This is a recap-ish of the latest podcast episode. You can listen to the episode below before or after you read. That’s because I tend to expand on topics from the pod as well as straight-up write about things that we did not discuss. The choice is yours in how you want to proceed!

I wasn’t expecting to write an article about Whimsy, but here we are. Honestly, the more you think about it, it makes sense for me to finally talk about— and see just how much its applied throughout my entire approach to menswear.  The term just feels so pertinent, so central to everything that I do, even if I never used it myself. After all, during one of the days it took to write this article, I typed this while wearing a sawtooth and cowboy boots…and on another day, a cape. Go figure! 

The idea behind this first came up when I was having a conversation with some mutuals about what it meant to be “into menswear”. Most of them said something related to how it’s about finding cool pieces (some of them were vintage pickers, but it was ultimately to be able to showcase your personality and taste. I didn’t disagree, although I offered an alternative. I want to play in my clothes. Buying clothes and putting together fits were a part of it, but I had the most fun simply being myself out in the world in a silly little outfit. We remarked about this particular approach, but it never came up again. 

Well, until a separate discussion arose.

I had another conversation, this time with Spencer, reminiscing on how my beloved article on Slouch is now five years old! At the time, the essay represented my entire philosophy on wearing classic menswear: you can have a casual approach to something colloquially seen as “formal”. As more people started to get into menswear during the pandemic, I simply wanted to show that classic menswear never had to be prim and proper, or at least didn’t have to carry itself that way. A suit and tie is still just another form of a jacket, pants, and a fun accessory, things that are in menswear all the time.

Today, “Slouch” has become quite the buzzword. No longer a pejorative for bad posture or a synonym for disheveled, it’s a positive adjective for easy, nonchalant menswear (usually in wider cuts). You can find it being used across various editorial copy, substacks, and your favorite menswear influencer (or budding content creator). I was just one of many on a similar wavelength; I am far from original!  But here’s the rub. As its use has become more popular, it’s become more codified. Even though I firmly believe that you can be slouchy in a full suit (or even a tuxedo with a bow tie), it really just means a dressed-down approach to menswear. It’s less of an attitude and more of a specific look, one that takes some ideas of vintage menswear and eschews the brash and exuberant (aka ties and hats), and opts for something more “cool”.

This was made apparent when I clocked how, when I referenced out in the interwebz, such as when Derek posts me on Twitter or Simon’s feature of my style (two accolades that I will always cherish), the outfits they pick are almost always the decidedly casual ones. You know, the stuff without ties and hats (or kimono coats and riding boots)— the bolder, dressier outfits. It hurts because these are the outfits that are most “Ethan Style” — and the ones I actually wear on a daily basis to do, well, anything. I’m more than just the slouchy outfits of me in a brown suit and a severely unbuttoned shirt.

It was clear that I needed to put forth a realignment. Obviously, I don’t need a sort of catch-all term for my approach to menswear; cores and codification can still be a form of dispassionate reductionism or, at the very least, a bit too “chronically online”.  Then again, I do admit that it’s nice to have some form of adjective to call “home”, something that others can hear and agree with, even on the surface. It’s human to want to be understood!  I just wanted to write about a philosophy that celebrated being extra for no reason, one that embraced the expressive possibilities of menswear, and that still felt casual— in the sense that dressing doesn’t need to be stuffy or overly pragmatic.  

The answer was quite obvious. People have been talking about it for quite a while, though not so much when it comes to menswear (specifically classic menswear). And when you consider my frequent use of riding boots, capes, and all of the Wizard, Jedi, and Ren Faire stuff I’ve been up to– all while wearing elements of menswear–  the term practically shouts at you. In fact, you might even say that they’re all related.

I wanted to write about Whimsy.

An Appropriate Descriptor For My Attitude

To me, Whimsy is a pure, wholesome expression of Free Will. This term encapsulates the Inspiration we get from seeing something “empty” —something that has the potential to be filled with energy and adornment—as well as the self-directed actions we take to fill the space. Whimsy involves creativity and sincerity, elements of personal taste, and the confidence to express them outwardly.  It is an attitude, an approach to life that is dedicated to adding amusement, charm, and, dare I say, life to wherever you can,  simply because no one else will do it for us (or at least not as often). 

In that way, Whimsy is about recognizing the agency we have, relishing in the fact that there isn’t a need to follow convention if you don’t want to. It’s about prioritizing and celebrating the self. It can only feel impulsive because it’s not overly calculated or concerned with optimization, but I do believe there is intention. There is a sincerity to its unseriousness.  This is why people compare it to embracing your inner child; it is not about being juvenile, but rather taking an earnest stand against the pragmatism of adult life, a move that seemingly was only possible in our youth. In other words, Whimsy is about embracing play. 

And so, while the term can feel cringe due to its frivolous perceptions or how it’s colloquially oriented toward the fantastical, I prefer to spin it as being wonderfully romantic, socially absurd, and decidedly intentional. Other terms can be similar (eccentric, dandy, and jaunty, to name a few), but I believe that they all stem from the theme of Whimsy. Its application can be a sliding scale, an overall theme that guides what you do.

It goes without saying that I’ve always been quite a Whimisical person, even if I never used that exact moniker to describe myself. Maybe I should have! 

My personality is quite big (more so when in loving company), being obnoxious and theatrical as I pepper conversations with riffs, non-sequiturs, references, and the occasional burst of song (just listen to the pod if you don’t believe me). [Thankfully, my friends do this too.] This genuine love for being silly and ultimately peculiar naturally comes out in my love of creating, whether it’s through photography, composing music, or painting shapes and colors. None of this is necessary for life, which feels quite whimsical. That being said, I think my output, like my music or my painting style, feels a bit Whimsical in its style (or specific technique and aesthetic).

Of course, this energy also goes into the things that decorate my life. My room is filled with adornments, be it quirky posters, vintage rugs, or various trinkets, all of which reference some sort of interest (history, art, and yes, fandom) and therefore bring me joy whenever I look up from my laptop or away from the incessant commercials from my cheap (or free) streaming plans. Hanging from a bookshelf (full of books, magazines, and vinyl) is a too-small-for-me belt back adorned with various pins and badges; this felt better than simply relegating those bits of metal to a box. It’s all maximalist, both physically and emotionally, bursting at the seams with sincere absurdity and joy. 

This all sounds mighty “extra” and “insufferable” (and decidedly Milennial), but believe me when I say that it’s all natural. There is no performativity here, no real rhyme or reason outside of passion.  We may have to thank my inherently boisterous Filipino upbringing, or the unfortunate fact that, thanks to a strict Christian schooling, I was never able to pursue theatre or filmmaking (I had to settle for church choir and making silly YouTube videos on my own). It just makes sense that Whimsy just came out, well, everywhere, in any place it could! There is a bit of intensity for sure, but I do think it’s more so that I am passionate about having fun. And yes, this obviously includes Menswear, an avenue I saw that allowed me to wear Whimsy on my sleeve and play wherever I went, beyond making jokes and doing impressions.

With its inherently superfluous and outdated/anachronistic nature, Menswear may just be one of the best examples that celebrate the absurdity of life in an external way. The choice to wear this mode (at least in a certain way) inherently conveys the attitude that not everything has to be so serious. And when it comes to tailored looks specifically, there are just so many components in an outfit to play with. Think of the possibilities, the nuances! 

And so, as someone who can never seem to shut the fuck up, I’m more than happy to walk you through how I see Whimsy in my Menswear, with the hope being that it invites you to develop your own eye and use it to guide your enjoyment of this hobby— and in life.

Details Make The Whimsy

The first part is about recognizing and finding Whimsy in garments. I do believe that every garment has an energy, an attitude. This could be based on the fabric, the silhouette, the design (lapel shape, belt loops), various additives (pleated pockets, pocket welts, belt backs), or their inherent history. I am not saying that you should reduce everything to a Whimsy Percentage, nor is it about seeing out the boldest items possible (unless that’s your thing, of course). No, I am simply saying that you should parse the expressive properties of a garment (whether minimal or numerous), understand its attitude, and ultimately decide if it has potential to work in an interesting outfit. 

Relativism plays a big part in this curative act, especially if you’ve decided to remain firmly in the tailoring mode of things. Now, suits and ties are generally quite whimsical (or at least just odd) when worn outside of External Occasions, but that energy can be played up when you consider the details of the garments themselves. The “timeless” ultra-fine, slim fit suits that were plentiful in my youth felt dispassionate and cold. Instead, I was drawn to the full-cut silhouettes of vintage and contemporary-classic custom tailoring, whose full cut silhouette provided you with comfort without sacrificing dynamism.  Wide lapels and the peculiar 3-roll-2 and double-breasted closures only furthered that Whimsical charm, not to mention the options for textured/drapey cloth in deep colors. It’s not that a full cut suit is the most whimsical garment in the entire world, but that it decidedly was more whimsical when compared to more agnostic, personality-less slim cut tailoring. Again, my point was to find this jaunty energy in my chosen genre. 

You can apply this approach to literally anything! Foulard and abstract geometrics (particularly vintage ones) just felt fun to me, especially compared to grid-like Macclesfields and medallions.  Vibrant repps and block stripes had more charm than the lines on a BB#2. Brocades in their iridescent opulence just felt so perfect in their “extra-ness”. Spearpoints and OCBDs with ample roll were more interesting than mundane semi-spreads and severe cutaways. Long collars and fuller fits not only echoed my taste in suit cut, but their slouch just felt more fun; this was emphasized by having striped shirts over solids (particularly reverse and Bengal varieties). Low-vamp loafers, with their dainty figure, seemed whimsical in how their feminine wiles contrasted against trussed-up oxfords. Again, this is about being cognizant of details and their potential energy.

There are also garments that simply have Whimsy throughout. Again, the exact level may vary, but it’s about whether you feel that they have it or not. Bow ties, sweater vests (particularly Fair Isle), berets and fedoras (or Tyroleans), colorful socks, madras trousers, white suits, saturated rayon shirts, a novelty cuff-link here and there; these are all no-brainers for Whimsy, each adding its playful energy each time I put them on. If your personality (and gumption) allows, I think it’s good to make space for Whimsy in your wardrobe. A pink chino, crazy wide shorts, a plaid bucket hat, a funky paisley tie. Purchases don’t always need to be functional or socially pragmatic (“cool”); there is always time for play. Funnily enough, if you enjoy the garment, you’ll find that it can be plenty versatile and applicable across different outfits; this is “forced versatility”. 

I feel that my embrace of whimsical details helped me get more comfortable with even bolder items, garments that might  “costumey” in how they deviated from menswear convention (or, how “regular guy” might not wear them). After a while, being a natty dresser, these also became natural acquisitions: white bucks, SFC’s extremely wide-leg gauchos, cloak/kimono-style coats, riding boots, and bib-front shirts, to name a few. These represented the culmination of my Whimsical mindset, as many of them served as an overt link between my love of menswear and fandom/cosplay. I wear these audacious garments surprisingly often, exponentially contributing to my already playful approach to menswear. Whimsy can be a positive feedback loop— the more you let it guide you, the more often it will come out! 

This leads to the DIY quality of clothing. After all, having a direct hand in your garment’s details is certainly a great form of playing with your clothes! While I have not cut and sewn a full garment myself, I have dabbled in some tangible creativity with my clothes. My beloved Senior Pants, of which I own four (and one short and one jacket), serve as a great way to literally add my appreciation of art (as well as cultural references and inside jokes) to regular cotton pants. These decorated trousers are indeed casual, but they have a particular energy to them. I’ve also done a fair bit of dyeing, which, despite mainly being trad colors (I’ve dyed white shorts to brown), adds a story behind the garment and therefore, a bit of Whimsy. 

It stands to say that being Whimsical was a foundational aspect of not just my  Foundational Wardrobe, but across everything I owned. It’s not hard to acquire only things that have kinship with your inherent personality! Menswear is already designed to prioritize defaulting and dispassionate creation. I simply wanted whatever I add to my closet to be as proud and excited as I am! 

The Styling Of It All

This considered and instinctual curation applies not just to the clothes we buy but also to how we style them together. Obviously, if dressing in a fun way is the goal, then having pointed garments in the first place definitely helps, but it’s only half the equation! 

I like how John Berger put it in Ways of Seeing,  “[All] its elements are there to be seen simultaneously. The spectator may need time to examine each element of the painting, but whenever he reaches a conclusion, the simultaneity of the whole painting is there to reverse or qualify his conclusion. The painting maintains its own authority.” I believe the outfit is this painting (or any comparable art-object), and so it’s up to us to take the steps to ensure that it holistically exudes playfulness from the start. 

Thankfully, this is quite easy with a playful wardrobe, or at least one that has playful pieces! It’s all a game of emphasis, choosing which aspect you want to play up. You could have a hero item take center stage, which could be as brash as a pink corduroy suit or as subtle as a patchwork madras tie. Sometimes it’s about adding a finishing touch that is just a bit off-kilter, like leopard-print Belgians with evening wear, a beret with a grey suit, or a jaunty scarf over a simple sweater and jeans in Early Fall. I even think subversion is a great way to be Playful, like wearing a rayon western shirt with a navy blazer, a Star Wars tee with a DB suit, or choosing white socks and leather loafers… with shorts. Dressing down something formal, making something casual a bit more dressy, adding in a reference to jazz-ivy, mod, or Westernwear, there is so much that you can do to make a playful menswear outfit. In fact, references in general are a great way to make an outfit whimsical. Even if the outfit I wear with a cloak or a riding boot isn’t exactly Star Warsian, its enough for me to feel like the throughline is there. It’s not unlike getting a brown plaid jacket in linen in order to exude an affinity for a Fall/Winter palette, even when it‘s warm. Whatever the case is, it’s about intentionally doing something interesting and pointed in a way that gets you excited to wear that outfit! If it wasn’t exiting, then why wear it?

Of course, your styling moves don’t need to be done at random. There’s also the act of using POV or character-based styling, which provides a sense of congruity, a narrative— bit of context, which may or may not actually be applicable to your life, beyond your enjoyment, of course. In other words, it’s fun to go all in and Full Send on a particular menswear vibe, just because you felt like it. Themed outfits are much like themed parties; they’re supposed to be fun! You could dress like a 1910s railworker with a bandana and Wabash chore coat, a mid-century ivy leaguer (or Mad Man) in a sack blazer and OCBD, a Golden Era leading man with abstract ties and big DB, a slick 1970s dude complete with flares and heeled boots at the club, or, to get meta, a Beams+ employee, with their earnest Amekaji looks. 

And even if you don’t feel like going 100%, you can always add elements of these themes into other “regular” outfits; perhaps the Whimsy can be that the railworker is going to church in a suit or that the Ivy-Trad guy wants a bit of western influence. Whether you want to be a bold character or one that involves nuance, every outfit will tend to lean on consideration and intention. That’s something to play with! 

Intricacy & Being Extra

While I certainly enjoy exploring all aspects of Americana, I do know that my heart truly lies in tailoring. As I said before, this attracted me most of all, simply because it had so many slots to plug-and-play with. It was like a blank piece of sheet music— and it was up to me to compose a song, one that expresses different elements of my personality and interests through expressive possibilities. Much like my love of a symphonic score, the narrow purview of tailoring presents a constant, intriguing challenge. I strived to make outfits that were delightful and avoid being business-oriented or overly concerned with “swag”, two things that tend to color most menswear content. At the end of the day, I’m a dumb nerd who wants to play with clothes! And so, I find so much enjoyment in playing with the nuances and adding even just a bit of Whimsy where I can. 

One example lies in shirt and tie selection— under a suit, of course. I had already noticed that in the 30s, they heavily used pattern mixing with their shirt-and-tie combinations, which were heartily employed even among business and cocktail attire. It was “dressed up”  or even “formal”, but it’s certainly interesting. I even clocked similar moves across contemporary brands like Drake’s, whose entire output was predicated on leveraging fun tie prints against striped oxford shirts (and penchant for cotton suiting, another fun move).

And so I seldom find myself wearing too many solids at once; doing so wouldn’t have communicated the energy that I wanted. Even when tempering my maximalism, I still have something “going on”; I usually have a patterned tie (foulard, stripe, abstract) or at least a striped shirt! Things can get even more fun when you add ties or shirts with a pointed character (Whimsy), like a novelty tie or a western shirt. Their energies only add to the myriad of expressiveness!

Exercising this agency made me even more into wearing tailoring, which naturally became my trademark, a second skin that feels effortless to wear, despite all of the “intricacies”. I apply the same thing to separates, where maximalism truly takes hold, as I could don a patterned jacket and odd trousers, two slots to play with instead of one (a single suit). Even though separates are already coded as casual compared to a suit, I still took advantage of the opportunity to play. It didn’t even depend on the weather!

Of course, my sartorial approach doesn’t stop at shirt-and-tie combinations. That’s just the tip of the iceberg! For most days, this would involve a harmonized or contrasting pocket square (that was usually exploding out of my pocket, adding to the Whimsy of it all) and a superfluous collar bar. I could also add knitwear (solid or patterned, all short length for high-waisted pants), belts, suspenders, as well as consider headwear and dramatic outerwear.  When it’s hot, you’ll still see me wearing hats and suits/separates, though I’ll add in saturated sport shirts, vibrant scarves, and a Panama. I will always try to max out the slots available to me! In fact, I often do that even when I’m dressed even more casually, like wearing a two-tone Hollywood jacket over a rayon shirt. 

I even think that my sartorial looks that lean toward “edge” and “swag” tend to still exude a bit of whimsy. In most cases, I think this is because the component items are still made up from my pointed taste; I do think that a flared leg, heeled boot, and or a black westerner are whimsical in their own right, even if it’s not as much as the others. I’m reminded of a fit I wore to a friend’s birthday, where I went tonal…save for a black tie with large cream polka dots. This outfit, with its mix of late 60s and aughts indie sleaze sensibilities, made for an amusing take on the Going Out look. Yes, a polka dot tie is quite Whimisical, but styling it in an edgy ensemble makes for a fun, pointed effect! 

Jaunty is the Key Word

There is definitely a discerning theme here, not unlike POV or some sort of “character”, that drives these decisions. After all, the inspo that compels these outfits comes from people (real and fictional/illustrated) who are inherently Whimsical and intentional in their maximalism: professors, composers, artists, writers, or radio psychiatrists who get offended when being called jejune. Perhaps this is because I have more in common with them (or I wanted to) rather than the capitalists; there’s something Whimisical about not going into business. If anything, they were at least all defined by a more casual approach to menswear— while still using a tie. 

All of them call to mind aspects of Ivy-Trad and certainly Apparel Arts, particularly how the latter pioneered the concept of “semi-sports”, which was about pairing elements of country attire (corduroy, sweaters, suede) with business-coded looks (navy suits, pinstripes). None of these looks (or characters) is sexy or louche (far from it, actually), but both the wearers and their clothes do exude a particular sense of humorous confidence, a cheeky flamboyance that certainly is played up when you bring those outfits into the modern day.  The costuming all over Wes Anderson’s films fit this vibe, as all of them are quirkily “just because”. There’s also “Bookcore”, as coined by Derek Guy to describe the indie and intellectual connotations these outfits tend to have, which was a good moniker, but I think even that can be reduced further. 

Jaunty feels like the right word to describe this particular attitude in menswear. It feels sharp and considered, one that does indeed lean into its effect on the outside world, relishing its dandy and now anachronistic styling. It feels much more at home when applied to sartorial looks, let alone those involving vintage styling. I feel like this describes me well, or at least a majority of my daily outfits: wild ties with striped shirts and a DB suit, riding boots with a plaid jacket and tattersall vest, senior cords with a blazer, a rayon shirt with fisherman sandals, or big shorts and a pair of white socks and derbies. Hell, even the move of wearing a vibrant sock with a tuxedo. Those outfits just feel and look Jaunty! As I said before, the term still falls under the whimsical umbrella, as being jaunty requires a whimsical attitude in the first place! If anything, jaunty can be seen as the technique and effect, while Whimsy is the base emotion. (Don’t think too hard about it; it’s not that serious.)

But as much as styling and making jaunty outfits is indeed quite whimsical, I believe that the real fun in clothing comes from wearing them— and walking out the door. 

Being Whimsical Means to Go Out and Play In Your Clothes

Whimsy isn’t just about making an outfit that looks Whimsical. Yes, that can be done, but I don’t want this to just be some styling guide or a list of reccs for specific pieces. Whimsy is an attitude, one that remains with you even after you’ve put on your fun little outfit. In that way, the term really is about going outside and playing in your clothes.

I understand that people tend to dress up only when there’s some sort of occasion that invites it. But I say, phooey! Nothing says Free Will like wearing a fun outfit to do something ordinary! Existence is the only excuse you need. After all, life has no dress code! Some may see this as a negative or confusing thing, so they relegate themselves to wearing vibe-agnostic outfits for fear of being seen as too much or too little. But that’s no way to live. I believe that our daily activities can always use a little spice to make them a bit more interesting and fun. You may even find that it makes whatever you do that day that much more enjoyable!

After all, so many menswear editorials are about being out in the world. Think about all the Drake’s shots from their heyday, showing the OG Crosby St. crew out for drinks and pizza, all while wearing equally fun sartorial combinations. Or how about my beloved Apparel Arts illustrations, which depict men in full-brimmed hats and collar bars, just… eating hot dogs or checking the time. Call it pretentious if you want, but that word means nothing if you truly enjoy it! And here’s the thing— you don’t need to be a menswear model or influencer to do such things; no need to wait for Buck Mason to invite you to an event or the next edition of Alfargos. I’d even say that my blog posts about what I wore to Hang Out, as well as the sillier, non-menswear (but still dressed up) stuff I do, are much more fun to write. I want to prove that you can just wear this stuff just because!

It’s not even that difficult; it just takes some confidence! But once you start, you’ll see just how easy it is to walk out the door to do anything — or even stay in — while wearing a fun outfit. Chances are, you’ve already come up with some bangers or at least have some fun cop that you want to wear out. Instead of waiting for some perfect occasion, why not just wear it out? Soon you’ll find that you can literally wear anything to do anything (relatively speaking). There’s no harm in wearing a pinstripe suit to a bookstore or senior cords to the bank. In fact, it may be important. 

You see, I believe that by going out in the world in a fun outfit, you may even gain more appreciation for your clothes. For example, you can see how they drape and move in ways that just don’t show up in a fit pic or outfit video.  Wearing clothes lets them age and gain patina, adding even more to their inherent Whimsy. You’ll also be able to introspect on what you like about the outfit itself and how it played into what you were up to! In that way, being out in the world and providing context to your outfits will help you build an even deeper understanding of yourself and what message you want to project to people. You’re missing out on all of this if you aren’t out there being dressed up! 

Of course, it goes without saying that fits do hit different when there actually is an external reason or an encouraged Theme. You can certainly seek out such events to help give you that impetus and build that confidence; Dapper Day certainly did that for me. I’m sure those in NYC or London have plenty of menswear events where you could wear something fun. It’s a bit rarer to find here in LA, especially if you don’t go to many fashion events (though certain bars and fleas have become the latest scene to get a fit off.)  Instead, I suggest you expend some Whimsical initiative and create those Occasions yourself! Take time to watch the symphony in black tie, have cocktails at home in a collar bar, start a book club and wear tweed, step out into the Ren Faire with tunics and riding boots, or make your own wizarding school party and wear a robe over something preppy. 

You can always find an excuse to dress up. But sometimes, you don’t truly need one other than just feeling like you want to play. 

Is This Just Cosplay? Yes, and That’s The Point— to PLAY

With all this talk about bold garments and themed outfits, I may feel like a form of cosplay simply because the outfit is too silly or “inappropriate” for everyday life. However, I see this as a badge of honor. People forget that cosplayers not only make the outfits, but they also go out in them. It could be a themed photoshoot, playing into the lore of the IP, or it could even be a bit of LARP, to show what that character could be doing outside of the script. Think Luffy at a Denny’s or Light Yagami at the park— how Whimsical! Such people are taking care to play in costume, showing that even with all their attention to detail, they are still about fun. 

That’s entirely what I want to do in my clothes. I want to play! The only difference between me and true cosplayers is that my outfit isn’t about recreating a specific fictional character, but instead, about playing up different aspects of my interests and emotions.  It could indeed be an outfit patterned after some approximation of a guy in Apparel Arts, 60s ivy, or 20s Western, but it’s still me! Can it LARP if you want, but the role I want to play is someone who is taking the time to enjoy his life, and having a themed or bold outfit is a great way (of many) that I can take. 

And so, I put on that shit every day! If you follow me on Instagram or have simply run into me in real life, you’ll know it’s true!  I’ll be in a white suit and bucks at the local cafe reading a book, wearing a fedora and a rayon shirt to pick vintage at the flea, or in riding boots and a bow tie while I go to Trader Joe’s; I’ll even be in cowboy boots and a leather jacket to visit my Lola! Yes, I could just wear a T-shirt and jeans to any of these things, but if I don’t want to, why would I? I’d rather wear something that excites me, something that is interesting and representative of my demeanor.  And so, I could even swap the outfits around, and it would still prove my point. Nothing truly matters, so we should take the initiative to have fun whenever we want. 

And because it truly is up to us, I’d also venture to say the fits that lean more toward being somber or louche will come off as Whimiscal in how they play into my regular outfit output. Context does matter— our own context! Again, nothing will truly beat out what we want to look like. And so, I could wear a tweed jacket for a night out, but I could also not do that. The decision not to dress like an Apparel Arts illustration or a mid-century advertising man and lean into something else is fun. This decision celebrates the agency we have when getting dressed.  And so, even if the outfit isn’t expressly whimsical because it’s conservative or intentionally toward sex appeal (or in how appropriate the outfit is for what I wore it to), consider how the outfits I wore before it were all much more dandy. The sheer contrast, predicated primarily on the arbitrary “what I want to look like that day,” just feels Whimsical. In other words, the Dichotomy is indeed crazy.

You see, I don’t have an “errand fit” much like I don’t have a “date fit” or a “flea market fit”. I mean, yes, I may wear an outfit when undertaking those things, but I’ll also wear it for other things before and after.  I only wear one outfit a day (save for days with a black tie event), which means that I’ll wear it to literally whatever I happen to be doing that day: going to Target, returning a book, dropping something at my dad’s, or a casual movie night at Serhan’s. All could be done in something preppy, Safincore, or equestrian. Some days could have a full docket, and others could contain one— or even none at all. It doesn’t matter in the slightest. 

I’ll wear whatever outfit I feel like, even to sit at home and do nothing, whether it’s waiting for its turn in the backlog (I once made 10 outfits in one go, just because the ideas kept going) or I’ll make something up on the spot (which could be casual or formal, who knows)!  There may be some small curation, as when you’re in your 30s, hangouts and events are more scheduled than spontaneous, but that doesn’t really change my approach at all.  All aspects of life can enjoy the spice of wearing a fun outfit! 

At the end of the day, this whole thing is like composing a song…and getting the chance to perform it. It really does make me happy to put something together and just wear it out! 

Conclusion

It really does seem apparent that my enjoyment of menswear is about play. As I’ve written before, getting into it was never about being fancy or formal; these were things I never needed to be. Silliness literally bursts forth from my soul! I never had to wear a suit and tie, much like how I never had to do a Bane impression (which has 2M+ views on TikTok, btw), compose a piano/violin duet for a crush in high school, or take photos of my friends. Menswear was just another place I could express my personality! The fact that I felt an affinity for a mode that was colloquially rigid, with cues that were anachronistic and costume-esque, only made it more absurd… and all the more intriguing!

Based on the state of online menswear, it seems that people can often forget (or ignore) that outfits are more than just content for people to “like” and “repost” online. Getting dressed is cool, and we can certainly make outfits that feel cool, but it doens’t always need to be predicated on “swag” or being in the in crowd.  The fact that digital accolades are worn as a badge of honor, or that you can be paid and start a side hustle (or career) by posting fit pics, only reinforces these unfortunate views. That’s why I think it’s important to take time for fun and embrace the things you enjoy, whether they have “swag” or not. I’m sure this mindset is why I am so vehemently against influencers and sponsored content/ads; you don’t need benefits to be whimsical. That’s not play, that’s a job. 

My hope in writing this is that people will understand that menswear, and fashion in general, doesn’t have to be approached so seriously. We can be Whimsical and take steps for joy and amusement, just well, because. It costs nothing (outside of buying the clothes we like) to dress boldly and take care to wear them out, even if that means that you’ll stand out. You never know; perhaps a stranger seeing you in a beret and suit is the impetus they need to try it for themselves! In any case, you should care for your inner child— the part of you that is unconcerned with optimization, the part of you that just wants to play, the part of you that is Whimsical. And thankfully, this attitude can easily be applied to all aspects: what we wear, how we wear it, and where we wear it.   

That last part is so important because I believe that being out there is truly the way to keep this message going. Yes, finding/buying cool stuff can be enjoyable, and putting together an outfit that fits my self-imposed prompts can be cathartic, but nothing beats putting it on and being out there in the world. It’s not about getting dressed up, but about being dressed up— no matter what you happen to be doing. I really do think you’ll find that it just makes life that much better, especially when you’re wearing a fit to do nothing.  You don’t have to do it exactly the way I do (not everyone wants to be a walking sartorial cacophony or look as anachronistic as fuck in a boba shop), but you should find your own way to wear outfits that both look and feel joyous.

Of course, it goes without saying that plenty of dressers live and breathe Whimsy already; don’t let my bit of pessimism make you think otherwise! So many of my friends feel the Call and step out in a fun outfit, whether we hang out together that day or not; they truly are full of Whimsy. And as much as I tend to be critical of the internet, MFAD, Weejawnz, and a handful of folks on TikTok and IG, all of whom clearly get fitted because they like it. I love that these communities even undertake regular “fit battles” that only play up the absurdity and Free Will of it all; the outfits in the competition themselves certainly are indicative of that.  In particular, I enjoy it when dressers talk not just about how they put together their outfit, but also about what they did in it.  Again, being able to go out into the world (class, errands, dates, work-from-home) in a fun fit is exactly what life is all about!

Can you teach someone to be Whimsy? Well, yes and no. I don’t think that the draw to be Whimsical— the ability to see life’s vacancies and feel invited to fill them with joy — can be taught. You either have it, or you don’t. But I think that most people do have it, they just don’t know it. You can definitely exercise your whimsical muscle and start to recognize just how much agency you have! It’s up to you to slowly branch out and add in that amusement as you see fit. You don’t need to go overboard like I do, but you might find it fun to take that time for yourself.

It doesn’t even need to be about menswear and styling specifically. I do think we could all benefit by doing fun things in our lives. Go paint in the park and hang whatever you make on your wall, regardless of if its good. Have a vinyl listening night. Go ham on Halloween, or better yet, host a themed costume party. Learn to play the piano. Belt your ass off at karaoke. Start collecting pins. Buy that dumb statue. Go to the arcade. There’s just so much play to be had! Get dressed up for those things…or better yet, dress up in a way that celebrates those activities.

Overall, it is hilarious that even though most of this article was about Going Outside with your outfits, the term I’ve used is one that is very trendy and “chronically online”. But I don’t care! I actually do find kinship with what Whimsy stands for. It’s more pointed than Slouch and still involves my beliefs about Tangibity, Occasion, and Standing Out, pulling it all together under one, wholly absurd attitude that is steadfast in the face of dispassionate pragmatism and social optimization. 

If centering yourself and having fun through instinctual curation and expression is considered Whimsical, then so be it! (Though it helps if you guys also take the initiative to make your own wizard murder mystery party full of lore, games, and costumes.)

[And yes, I’m giving you guys permission to call me “Jaunty”. I feel like I’ve already peppered it in throughout the internet by now…]

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Always a pleasure,

Ethan 

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