The Going Out Look


Let’s explore a new POV: what we want to look like when we “go out”. The answer is something a little cool, a little sexy, and a little slouchy, all while using pieces we already own in a new way.

Before you read further, listen to the podcast episode below. It is technically Part Two of our interview with John Robinson, but I think it’s a very good standalone topic.

Is the blog header just our version of the “going out shirt” of the late 2000s?

Do you guys remember the “going out shirt”? If you don’t, I suggest you read this GQ article from 2013. Or just check out this excerpt:

“It is the bro’s uniform whenever he goes to clubs, bars, house parties, or—god help us—dates. It is always worn untucked with jeans (boot cut, of course), and is considered the “dressed up” alternative to a T-shirt or polo. Whether gingham or striped, rumpled from the hamper or neurotically over-starched, it is, in short, an abomination.”

– Scott Christian in “Men, Time to Ditch the Going-Out Shirt”

Presumably fresh from reading The Game‘s chapter on peacocking, men in the early to late 2000s would wear “going out shirts” any time they…well, went out. As the description suggests, it was meant to be an alternate to the regular things in a man’s wardrobe. Christian calls out that it’s mean to be more formal that typical casual attire, but when you look at what Google Images produces, its clear that this obscenity was mean to be more than just a casual shirt. It clearly gaudy (not in a good way), but maybe that was the point. The patterns and colors are so bold- if it wasn’t striped or checked, then the shirt was made of a solid color in some shiny material (I’m thinking of those solid black or saturated single color shirts). It would be difficult not to notice it in the bar, club, or whatever locale your nightlife endeavors chose to situate itself in. I even feel like the going out shirt trickled into what teens wore to prom, where the idea was to be flashy and stand out with (or for) your date.

But despite all that, I have to cut the “going out shirt” some slack. Why? Because the idea was that the shirt was something different. With it’s bold patterns (usually striped or checked), multiple buttons, contrast placket (or collars), and slim fit, this shirt was mean to evoke the ideas of a dress shirt (meaning corporate) but be more fun. You’re not at the office and you’re not at home. You’re going out.

My going out look, or rather the more casual one. You’ll see variations of this throughout the essay!

Now while I understood that sentiment, keep in mind that I was still pretty resistant to it. That’s because I never saw myself as a going out guy. I’m a nerdy guy with theater kid tendencies. I couldn’t imagine doing anything that was considered “going out”, let alone wear that type of shirt. There was probably some insecurity there, but honestly, my hobbies and friends weren’t conducive to that kind of life style, even as I entered my twenties. Boba hangs and watching movies wasn’t “going out” to me. Having a late night drink at a bar was- and that seldom happened to me. I didn’t even drink coffee!

It’s not that I didn’t have great fits when doing activities with my friends, but it never had that “going out” vibe. To me, the vibe is a bit peacocky being equal parts slouchy and sexy. But in that stage of my life (around 2015- even 2019), I didn’t have many opportunities to be fully “Ethan”. I was in college (and later working at Ascot Chang) and while my outfits were bolder than the average guy, I was still conscious about how much I was doing. In short, I would save the Full Ethan fits for particular hangouts with my friends, providing the opportunity for us to get a little SaD and match each other’s energy; it’s a different vibe than simply dressing for work. Sex appeal and being flashy was low on our list of priorities- we just wanted to be able to wear spearpoint collars and white socks together and not on our own.

Reflecting on this is quite funny, since it proves that style is a journey and your stage in life certainly echoes that. I wouldn’t say that the stage I described was lacking in confidence (many of the essays I reference today were made during that time period), but rather that my lifestyle wasn’t conducive for going out. The idea for dressing for flash just didn’t cross my mind, since I was too preoccupied with being able to wear my wide lapels with military chinos or reconciling a way to get what I wanted from both contemporary and vintage menswear (as well as with a healthy dose of streetwear and merch). Basically, I was still becoming fully formed.

The company I keep (at least in regularly) also reflected this exploratory stage. None of us really had any want to go out, presumably because we were still busy figuring out our careers or working through our final years of university. Our clothing stayed trad, ivy, and vintage. It didn’t matter if it was perceived as stuffy because our slouch would take care of fitting into our context. Some of us made our context fit it, by working in menswear directly, hanging with the community, or having other ways of adjusting the life to our clothing using Forced Versatility or Practicality. We’re still young, but I think most of us had accomplished what we set out to do. We were the photographer (or journalist, or gamer, etc) who happens to wear classic menswear.

After a few years of the awkward Old Ethan, it certainly feels empowering to finally be who you want to be and to pay no mind to the context. There is some editing for specific things (like work or going to the pool), but overall I’ve been able to dress like me, whether that’s the Esquire Man, a Brycelands knock off, or a guy who is a bit too obsessed with Take Ivy. As my friends and I started to get more honed into our careers, we were suddenly able to wear what we wanted any day of the week without waiting for Dapper Day, Inspiration LA, or ! So what’s next you ask? Easy: going out.

Going out is a new experience for me. I’m not sure if it was COVID or the fact that I’m entering our mid twenties, but I’ve been going out more. Perhaps I was fed up with simple boba hangs and wanting something with more edge. Or maybe that with this new found confidence in my style (and a new career), I wanted the next challenge of going somewhere unfamiliar- like the bar or lounge, rather than a friends’ house to play Smash Bros. I’ve probably always wanted to go out (yes I’m acknowledging the very sad boi-joker past I had), but lacked the ability to do it effectively, both in the clothes I wore and the company I kept.

As I’ve gotten older and more established, I’ve been able to make more friends outside of the ones I had in college- friends that didn’t mind having a drink or staying out and conversing without a silly movie or videogame (not that there is anything wrong with that). To my surprise, I actually was being invited to bars and parties now- this is something I never thought would happen.

I think that my current friends were feeling the shift too. Maybe they just watched too many 70s films or finished the Sopranos for the 3rd time, but they seemed to all want to go out. Not with crazy night life, but just to go out for a change. It’s pretty funny to see MJ, Spencer, John and many others make the jump to go out. It’s a little less wholesome compared to our midnight ice cream hangs, but it’s still us. Maybe the pandemic made me more comfortable with going out, drinking a bit of spicy water, and perhaps being “that person” I envied back when I was in college (whatever that means).

In that same vein, I’ve noticed a shift in how we dress when going out. It’s still the same people with the same clothes, but with a bit more edge. There’s slouch, but there’s also that sex appeal. It wasn’t exactly a “going out shirt”, but a going out fit, made up of things we already owned- just with a different attitude. After all, most of us tend to keep our clothes for a long time and like the challenge of recontextualizing it for this next stage in our style and by extension, our lives. In other words, we’re getting sexier. Who would’ve known that this group of nerds would finally arrive at the party? Better late than never!

Now as I trace the idea behind “going out attire”, I’ve found that it really a culmination of everything I’ve talked about on the blog thus far. At the forefront, this type of fit is rooted in an intentional POV that takes context into account (that last part is actually quite important since it might be the first time we’ve been actively dressing in that regard). At a bar, you might be surrounded by guys in “going out shirts” or at the very least, the typical straight man date look of a slightly fun shirt with some sort of solid sportcoat and pant (maybe a matching suit trouser, dark chino, or jean). A big part of developing this new POV was basically figuring out how I (and my friends) could do that ‘uniform” or vibe (that clearly has some appeal) while still being me.

Now you might think that any of my outfits are fine, especially as I’ve been the Esquire Man to a few things already. But now, I like pulling a bit more inspiration than just Drake’s and Apparel Arts; I want to be more than just ivy-trad or just wearing jeans as a shortcut to “going out”. I’d like to think I have nuance and I narcissistically want to show my range. Call me misguided, but I want to show that the ideas of trad tailoring can still be cool. That you can intentionally wear it out.

You guys know that I have little bit of that 1960s-1970s groovy flair to reference now. There’s also that sleezy 90s yuppie look, as well as the Seinfeld-Sopranos mixture of sportswear and tailoring. And if we were being truthful, I would say that there is definitely a bit of appeal in that early 2000s going out shirt look, though with a focus on dark solids rather than flashy patterns. All of it just needs to be taken through my POV of vintage and contemporary menswear. It’s different than simply wearing a bucket hat or a workshirt to show that you aren’t corporate. It’s about creating a different vibe. Something sleek, sexy, and perhaps even cool combining the ideas of dark corporate cocktail hour with the sexy 70s movie star vibe, all within the pieces I already have. I’m not about to buy a whole new wardrobe just to go out!

The idea is to not look trad or corporate, but still retain ideas of both. It’s not as bold as the fun shirt I posted earlier, though its on the same throughline. I feel sexy in it lol.

A few specific pieces are favored during going out looks and most of them are alternatives to my regular trad clothing. Instead of striped spearpoints and OCBDs, I tend to favor solids ones, either in dark colors or plain white, echoed with plain ties. It’s a bit plain, but the vibe is more about sleekness than being sterile. Funnily enough, going out has given new life to those seldom used pieces, as plain/solids aren’t exactly the most utilized in my wardrobe; I’m quite glad I invested in them in the past!

When “going out” with tailoring, it’s almost echoing all of those douchey, prom-ish looks that we’ve come to eat from early 2000s menswear. But maybe that’s entirely the point. It’s an excuse to wear solid dark colors, especially after years of menswear blogs telling you that you shouldn’t. But instead of wearing a navy non-iron shirt, you’re doing it with a faded denim westerner against a Crispaire suit or a black knit polo and a grey tropical trouser and a slouchy chore coat. Going out just needed a bit of refinement and taste. Monochrome and tonal looks just seem appropriate for a dimly lit bar or restaurant. I’m really leaning into European tailoring from the mid century- think Le Sans Blague from The French Dispatch.

Color can still be used, but it should be smart. A bold striped shirt is a great choice (to echo the beginning of this essay), but it doesn’t need to be worn on its own with boot cut jeans- it was just waiting for a somber black tie and a dark jacket. Maybe a bit of The Game‘s peacocking flair can be referenced with a jaunty scarf, a beret, or a bandana (which I have yet to write about). To be clear, the goal isn’t to get laid (in fact, none of this is good advice for that) but instead just to have a cool outfit that is a just a bit different than what you wear regularly, at least in terms of attitude.

Of course going out is also easily done when you have dedicated pieces that are more conducive to it. A slouchy navy hopsack sack jacket is cool and works great with jeans, but a double breasted version just has bit more dramatic flair that simultaneously signals menswear and yet subverts it depending on how you wear it. Wearing a dark DB with black jeans and a merch tee is a great way to pull the 90s look together without doing it so straightforward with lightwash Levis and retro sneakers.

A rayon sportshirt is also something I wear when going out. It may not work with a tie, but it still feels a bit more interesting than a polo shirt or even a chambray workshirt. The blousy cloth just feels slouchy and when you have it severely unbuttoned, it adds in sex appeal. Sure, you could do it with shorts and jeans like most guys, but adding in the sportcoat feels a bit more “menswear”, keeping that POV alive. Let’s not forget that men have been wearing slouchy sportshirts with tailoring for nearly 80 years. SLP brought it back with skinny jeans and sharp jodphur boots. Now its my turn to do it my way!

Jewelry can also help, though admittedly it’s not something we’ve covered before. Black shirts (that are severely unbuttoned), dark ties, and slouchy DBs are great, but we can’t forget how great true hard ware is. Adding in a western necklace, bangle, or ring adds a bit more of that “peacocking” that tends to go with this theme- it’s also much more sexy than a silver collar bar. Wearing jewelry with a menswear Going Out Look can be bit subversive, perhaps a bit rockstar but I like that. Think of it similar to the metal zips and clasps on a leather jacket (which used to be more for workwear) or the brass buttons on a blazer. A few people might assume that its all rather negligible since jewelry isn’t on the garment itself, but that’s all the more reason to incorporate it. Its a subtle move that gets you in the mood to go out.

To be clear, there’s nothing wrong with going out in straightforward trad clothing. I still do it occasionally! There is a separate appeal to rocking a gingham shirt and repp tie or an OCBD and a seersucker jacket at the bar. It’s a bit like an “intellectual went out” or what you’d see at a University final club in the 1950s. To make it more conducive for “nightlife”, you can always take off your tie and unbutton your shirt. But then you run the risk of looking like a regular biz caz guy off the clock rather than someone going out. There’s nothing wrong with that, but you have to admit that its a fun challenge to try and take that trad clothing and filter it through the idea of going out. Sometimes you don’t want to be a group of history professors at the pub. You want to [try] to be the cool guys who happen to be wearing cool clothes (and maybe a sportcoat). You need a bit of edge and sex appeal. Well, with at least in the dosages that classic menswear allows and hopefully this essay (with its plethora of photos) proves that.

This whole topic (like much of what I write about) should be considered a loose guideline for a POV. You can certainly wear gingham to go out just as much as you can wear a slim black jean. This isn’t supposed to be a list you can check off. Sure, some pieces are more conducive to the look like a leather jacket or an aloha shirt, but I like the freedom and challenge to turn a piece into a going out one. I think that the photos I’ve included at the end are proof that all of what we like gets a pass, from an navy blazer and blousy aloha to a wide legged grey trouser and even a normal striped OCBD. It’s all about the attitude when you wear it. But don’t let it intimidate you- it’s supposed to be fun!

It may just be as easy as using Forced Versatility, though now you are adding edge and sexiness to it. You know, for going out. It’s fun to lean into the confidence of the going out look, even with the added irony that you’re wearing “vintage-esque” tailoring with high waisted pleated trousers and wide lapels. It’s a conundrum that just makes it that much entertaining. As John and I discuss in the podcast episode, its simultaneously dressing for yourself and others in an environment where the only rule is to “be cool”. You can’t rely on a corporate dress code or some formality rules to save you. You just gotta get good.

In my mind, the Going Out Look is almost about bringing the concept of slouching in menswear to come around full circle and point it in a different direction. Instead of blending in with slouch, its about showing that you have no problem going out in the outfit you’ve decided to wear (perhaps confident slouch is the move). It’s proving that tailoring can be considered just clothes, but now we know that these clothes (which have trad roots) can be spun around and be cool at the same time (context pending). Classic menswear is formal, casual, practical, and now it can be worn out for drinks. Furthering the idea that sportcoats, dress shirts, and trousers don’t have to default to simply being seen as work attire or something an “adult should wear” is entirely the point of this essay. I mean dressing intentionally is always going to be silly, so why not have fun with it and get the most out of your clothing?

The entire idea is to be match the energy of the place you’re going to. Kiysohi (in my Patreon) is a big fan of this, where he mentions that as he lives in the city going to dive bars and art galleries, trad clothing (meaning OCBDs, tweeds, grey flannels) just doesn’t make sense. I’ve been understanding this more and more, especially as I start to have a wider, non-menswear context in my interactions. A going out look should display some social cognizance but with a bit of personal narcissism, showing that “hey even though I am a guy who likes to wear suits, I can still go out”. It’s almost like you’re accessing your inner douche or at the very least, your inner “IG Explore page menswear guy” with a bit better execution and cohesion. Going Out is just a new POV to add to your arsenal when creating an outfit.

I feel like I’ve already been doing this in practice. If I know I’m going to an night event, I try to wear darker, sleeker colors almost to evoke the ideas of evening wear, but within regular (non-event) tailoring. There’s more black. More suits rather than my beloved separates. My charcoal brown suit with a vibrant stripe shirt and solid tie worn to the first Dapper Day Soiree is a good example of this. It’s about finding the “going out” look in what you already own, though it does come to mind when buying new things. I’d even go as far to say that my new experience with going out has lead to an even more nuanced philosophy when buying clothes.

Not only does what I buy have to work with my 1930s-meets-Styleforum approach to tailoring and my love of ivy-trad and Japanese Americana, but it now also has to be conducive for going out. And to my surprise, that still encapsulates a lot of things! I’m not sure how my taste has gotten there, but as you guys already know, a lot of my wardrobe is quite interchangeable. A spearpoint works equally well with a foulard and a bandana. A brown cotton suit looks sharp with a chambray workshirt and a dark rayon. A dark club motif tie is looks good with OCBD + tweed fits, but it also becomes a focal point when worn with a somber suit and shirt. Versatility is key, not in formality but in aesthetics.

I also had the realization that a going out fit doesn’t just mean to go monochromatic or wear only black (though both of those things do help). The truth is that dressing for this particular context simply requires a different attitude and POV when creating an outfit. Perhaps its the mature thing, to acknowledge that you don’t want to just be ivy-trad professor all the time. You want to have an edge while showing contextual fluency. I think that’s perfectly valid. The Going Out Look encapsulates all of that, allowing you to look “sexy” (relatively speaking) while still keeping the ideas of vintage and classic menswear that we all love so much. It’s a fun provocation, adding a new facet to the creative outlet of dressing up. AKA, we can be that going out guy, just in our own way. And it certainly helps that other menswear guys are leaning into it too, from our favorite style icons to our actual IRL friends. There is inspiration to be found everywhere, and you can certainly see that in the photos I’ve included below.

I could consider it a personal challenge, not only to recontextualize my existing clothes, but to actually find the context for these mode of dressing. Maybe all the years of seeing the Drake’s (and later, J. Mueser) boys hanging out at dive bars with somber suits and ties finally had an effect on me. Maybe it was the fact that it took me until now to find my own crew and get to a stage in life where doing that sort of thing felt normal rather than foreign. I never thought that I’d be the kind of guy to use his style and dress in this way. For a long time, I thought I was relegated to simply being a slouchy Gen Z-er who dressed like an old man and not in a cool way. But as I gained a bead and grew out my hair, I realized I could be that guy. I could be going out.

I may not be picking up girls and doing shots (at least not presently), but I’m perfectly fine wearing a cool fit that is not decidedly ivy-trad while sipping a Whiskey Sour (or cider, lets be real) with my pals, especially considering everything that’s happened over the past two years. Going out is actually fun! It’s really hard to believe that the nerdy guy I always thought I am is finally able to partake in what is honestly a normal thing without getting anxious. Maybe that’s a sign of getting older and more confident. Or perhaps it’s because I can use my clothes to be that person I envision for myself…along with cool friends who also just get it. Going out isn’t something to avoid- it’s now something that I actually enjoy and can see myself doing often!

More over, it’s proof that slouch isn’t the only thing I can do. I can be cool too. If I fail, don’t tell me. It’s finally a chance to for me to intentionally be edgy, to peacock a bit, and to lean into the sexiness and elegance we know deep down that we want to exude. We’ll make it happen, at least with our fits.

Podcast Outline

  • 04:49 – Going Out Attire and Being Sexy
  • 14:05 – What Do You Consider an “Event”?
  • 24:38 – Wearing Anything to Go Out
  • 31:48 – Mentalities for Going Out
  • 42:34 – Date Attire
  • 53:00 – Favorite Going Out Pieces
  • 1:00:54 – Wrap-up
Not Esquire Man, but still tailoring. And definitely conducive for going out.
Quite 1960s to me, despite using stuff I already owned.

Asian Men Club High Resolution Stock Photography and Images - Alamy
This whole thing is basically our version of doing this.

Different styles, but they have that “going out mood.
An unbuttonned rayon scarf, dark jacket, and jeans is a great shortcut.
Seriously. Going severely unbuttoned can take you from normal to going out.
Dark shirt and plaid jacket. Cool move.
Casual is sometimes a bit too easy.
I mean it looks good!
But I like the personal challenge of taking my tailoring out of trad and corporate attire and putting it out.
Sometimes you can mix classic menswear (polo) with something unique (like this noragi) to give it an edge.
Or you just lean into tailoring. Andre does it here with a low buttoning DB, open shirt, exposed undershirt, and some bold glasses.
I’d argue that wide is just as louche as slim looks. The slouch makes it conducive to go out.
Husband’s 70s inspired tailoring naturally looks like a going out fit.
Jeans + chelseas added to tailoring is a good move.
Severely unbuttoned. A spearpoint collar worn open even mimics the disco shirts of the 1970s.
Dark colors are great for going out.
Cool sunglasses too.
I prefer DBs over SB’s when going out.
DBs can even help envelop a bold color.
SBs aren’t totally bad though.
Bold pattern mixing.
I should have just called this essay “you should go severely unbuttoned”.
I’ve been doing it a lot. It’s like the polar opposite of my striped shirt + foulard uniform.
Attitude is all you need.
OCBDs can be cool for going out. I like how John wears his with raw hemmed flared jeans and boots.
Mine is a bit more boring, but the DB helps!
Self explanatory.
This is pretty good for going out and it doesn’t even involve a collared shirt!
Sora is a master of the tee and sportcoat look.
I need to write about DBs already.
Dark shirts with abstract patterns >
Threw this in here because to me a DB is similar to a double rider. It’s dramatic and sexy.
Spencer’s idea of going out is still more rugged than mine, but I like how he retains tailoring in there.
Jake Mueser.
Not super sexy, but the dark colors work here.
Brown suits in the city are underrated!
A western belt is a good accessory.
More of a preppy going out look.
This is very similar to the outfit I posted early in the essay!
Spencer doesn’t have black clothing, but he still retains some of the same ideas: western belt and fun patterned shirt.
Think of a going out look as cocktail attire, except you’re free to wear whatever you want.
James also has a penchant for houndstooth.
Adam doing his own interpretation of that 70s movie star look with his new navy hopsack jacket!
A more rugged look, but the dark shirt and shoes help sell this as “going out”.
Lots to enjoy here. Jaunty scarves, slouchy cords, dark colors, and a turtleneck.
It doesn’t have to be tailoring, though being adjacent to it helps.
Patterned shirts!
Spencer has been dabbling in my “uniform” but in his own way.
Sometimes you just gotta bring the black tie vibes in. That’s the ”ideal” going out look for menswear enthusiasts.
Now a bandana or scarf is a good way to add some extra flair. This may need it’s own essay.

It instantly helps class up a tee or unbuttoned shirt and looks fantastic under a jacket.
It can feel more intentional than just unbuttoning your shirt (which can feel a bit bizcaz).
Jay loves doing it. It’s done almost every time we go out!
With suits and ties, it’s almost like we’re ironically-but-unironically doing this look.
Of course we still love the idea on using a tie. Hopefully these are proof that ties are still a great part of Going Out Fits.
Dark shirt and dark ties can feel prom, but at least our execution is better than when we were in high school!
My black knit ties get the most wear after I decided to go out more.
Trad still works at the bar! Note how I used a black repp tie.
Cocktail night is a vibe for tailoring enthusiasts who want to wear a tie.
This is a bit rugged- might have been more “going out” with darker trousers (preferably in wool or something more sleek).
After a long span of wearing patterned jackets, it’s nice to come back to something somber.
The left is a vibe.
Cocktail hour!

A “casual” tuxedo is a great going out look if you want to get a little bold and rebellious (against the fogeys of menswear that is).

Dark foulards are fine at the bar.
I prefer stripes.
Or knits!
Light solid ties are my current jam.
It’s hard to tell, but John is wearing a dark shirt and a dark tie.
Adam’s interpretation of a Going Out Suit Look: dark tailoring, denim shirt, and a dark repp tie.
Tonal looks, black knits, houndstooth, and flared pants are great for going out.
Two types of going out attire that involve jackets and jeans!
Arnold’s bar look seems very 1940s.
Bold stripe shirts echo that early 2000s vibe, but you just gotta make it more menswear.
Michael Drake on the right gets the going out look: dark jacket with tonal shirt and tie combo, all in deep blue family. More slick than regular business wear.
Drinks with Mark Cho! I’m in dark separates and a dark motif tie and Ryan has a cream suit and dark shirt with black pennies; Mark just has grey flannels and a bold blazer. All different interpretations of going out looks!
A bolder Going Out Look, but one that is quite fun!
Matt and Stephanie of the Bullshot Bookclub, taken by Chase.
Going out in a suit is fun.
A light variation of my previous look.
We all coexist.
Brown in town!
Two variations yet again, worn to a WM Brown event. I guess I’ve always liked dark tailoring for special occasions!
Trad, but still slick.
Leaning into the bold rather than being minimalistic/dark is an expert move.

Thanks for listening and reading along! Don’t forget to support us on Patreon to get some extra content and access to our exclusive Discord. We also stream on Twitch and upload the highlights to Youtube.

The Podcast is produced by MJ.

Always a pleasure,

Ethan M. Wong


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