Despite my obsession with tailoring, vintage ties, and felted hats, I’d like to think I’m a practical person. All my clothes serve me just fine in my everyday life, with breathable fabrics and a plethora of pockets helping me get by in my soft-handed, city boy life. 

I’ve always tried to push this “Practicality of Menswear” theme in everything I do to show that these purchases can be fun and yet perfectly applicable to everyday life. I’d also like to think that despite each of these things being coded and rooted in historical formality, they are perfectly fine to be worn out socially (YMMV), removing the idea that these are precious or too costume-y. Who says that an Account Manager can’t wear white bucks or a beret? These are just clothes! My clothes. 

What I’ve noticed is that, outside of Safincore and my predilection for Kimono coats, my closet is rather “normal”. It’s trad, with a lean toward 1920s-1940s proportions and designs. Nothing feels too wild when you put it that way, even if it’s anachronistic or read as “formal” by other people. I’d like to think that my styling and overall attitude help sell this easygoing vibe.  

Lately, I’ve been wearing something that puts a wrench in that sentiment. A garment that is rooted in the era and aesthetics that I like, but is certainly much more expressive and bold; it might be the most absurd thing I’ve ever owned. It’s something that I’ve always wanted, even before my menswear tenure; I actually appreciate that menswear allows me to wear it out, even if it’s still a wild choice. And if anything, owning this garment has helped further the idea that, despite all the talk about practicality, menswear is still fun, which means we can make space for the things we just want to wear for no reason. After all, I do love a silly little tie! What function does a tie have now, especailly in a world where it’s not required for office wear?

So without further ado, allow me this space to talk about my beloved Riding Boots. 

Despite their completely superfluous use in my city boy life, riding boots are indeed a practical garment…historically speaking. The Wikipedia entry on them (as well as this article)  provides a great overview. These boots are made for riding horses, with their long shaft protecting your legs from friction against the saddle. Tall motorcycle boots follow a similar pattern though they’re used to stop contact with hot pipes and machinery; it’s no surprise that early aviators also tended to wear Riding Boots.  After all, boots were indeed meant to be tall. 

Despite their practical use, the Riding Boot reads as elegant and fancy. The boots are inherently tied to all things equestrian such as dressage, fox hunting, or polo, all of which are the tradition-heavy and leisurely activities of high-status individuals (they have to own horses after all). Even in terms of militaria, officers were the only ones who would have such boots, simply because they were the ones who would ride the horses. This context turns this discerning piece of menswear into something traditional, with an anachronistic charm that’s also found in Stroller Suits or a white tie rig. It’s probably not something a regular menswear guy needs but if you have an appreciation for vintage, especially Golden Era styling, you might find yourself drawn to these silly little pieces of footwear. 

Riding Boots are also just aesthetically pleasing. In general, long and sleek objects tend to have a “sophisticated” air to them— just look at a classic Rolls Royce or the “prestige gap” concept. As such, the most iconic version of the the riding boot is black with a long, uninterrupted shaft, though brown versions (and “tan tops” for hunting) as well as ones with zips and laces did exist. In my search for riding boots, I found that classic ones are still made today, though they are pricey no doubt due to the amount of leather used; cheaper ones are made from full synthetics. There are also modern models with commando soles to help with traction on the ground, an innovation from the leather soles of the iconic versions. Of course, that rugged quality may detract from the streamlined aesthetics of the classic riding boot. Riding Boots just make sense when they’re tall, lace-less, and smooth.

As a result, Riding Boots are decidedly a fashion item, with the bonus being that they are fancy, traditional/historical, and practical…at least for the specific activity of riding horses. While the boots are mainly worn with dedicated equestrian or hunting attire (as well as the uses of breeches or jodhpurs), there are plenty of photographs and illustrations of people wearing them outside with “normal” clothes: sweaters, dress shirts, ties, and especially blazers and sportcoats (though some sportcoats are paddock style and were cut/designed to be worn while riding).  Men and women could be seen in such attire whether they were fancy folk, aviators, cyclists, or even archaeologists. Their abundance in photographs, advertisements, and especially Apparel Arts shows that the fashion heads of the day certainly signed off on it. 

The combination fascinates me, as wearing Riding Boots brings with it a variety of connotations, melding formality, militaria, and adventure with a trad outfit. Footwear has always had this expressive power, being your last footnote (heheh) to the expressive direction of your outfit. I don’t mean this in terms of casual vs formal but in terms of narrative and thematic merit; suede chukkas and white bucks are both more casual than an oxford but they still communicate different things, being rugged and leisurely respectively. 

However, the expression of a Riding Boot is decidedly bolder and does more to “casualize” an outfit than by simply chunky commando sole derby. Riding Boots bring in Equestria and its unique combination of practicality, elegance, and historicism; it’s casual but not rugged, sleek but not inherently formal (especially when worn with tweeds and field shirts). It feels leisurely but not in the same way as a loafer or sandal, where the lack of structure is what makes it feel easy to wear. On a similar note, we also can’t forget the crazy effect on proportions, as the boots are high and tight, which slims the legs considerably and in turn makes your pants blouse, making for a fun effect against the inherently clean geometries of classic menswear.  It feels British (or European in general) and decidedly American (just look at how Ralph uses it), which again adds to the character of your outfit. 

But despite the Riding Boots’ expressive character and how tied they are to Apparel Arts, it wasn’t enough for me to consider buying them for myself. No, the purchase finally came about because of Star Wars, Renaissance Faire, and you guessed it, cosplay. 

My real love of Riding Boots comes from Star Wars, full stop. 

It was a fantastic choice by John Mollo to incorporate tall riding boots in the costuming for Han Solo and Luke Skywalker (the throne room finale). Since then, tall leather boots have been a part of the Star Wars look, worn by Jedi, Rebels, Imperials, and even civilians. It seems practical for the myriad of environments you could encounter in their galaxy and provides a sense of adventure, which could happen at any moment. These boots help Star Wars feel familiar to us, even when combined with the overall sci-fi-meets-Asian designs that permeate through the rest of the Star Wars fashion aesthetic. 

It’s not that I’m a regular Cosplayer, but I like having the agency to point my attire into a niche aesthetic. And when it comes to Star Wars, it’s not enough to dress in Gorp. You need Riding Boots. That juxtaposition is what makes the look! I’m reminded of when I visited Disneyland with my ex last year and wore a Galaxy-inspired fit with a sport shirt, brown pants, and my old utility vest (that I barely fit into), though I think it was clear that my footwear was pulling me down. I’d say the same thing for dressing for the Ren Faire. Having Riding Boots would have come in clutch…and it was obvious that I would easily wear them quite a bit outside of cosplay/LARP outfits thanks to all the vintage inspo. They would be a truly versatile and yet “inauthentic” purchase for me.

It was my friendship with James that actually pushed me over the edge.  He’s a menswear guy (who prefers sleek 70s/Husband-esque fits), but he’s also a huge nerd who doesn’t shy away from going Full Send (he did Homestuck makeup for my Tumblr birthday party). A few years ago, he told me that he cobbled together a full Ren Faire rig, which included vintage knee-high Frye boot that instantly made his LARP fit better. Since then, James has worn his boots to a few Star Wars-themed events, showing that they indeed helped sell the look (more than if he wore his Cuban heel boots). I knew that I should just do it. Riding Boots just make sense for us cosplaying nerds who want to look like adventurers but have never ridden a horse outside of Knott’s Berry Farm (a SoCal experience). I at least wanted to make sure I had them in time for Ren Faire 2025, where I decided that my outfit would go even harder than last time. 

I eventually acquired my pair of Riding Boots after long weeks of scouring and waiting on eBay. Like with most things, I preferred to find a true vintage version instead of simply a cosplay or repro/reenactment version, which would either be low quality or expensive, respectively. Eventually, the eBay gods heard my prayer, as I ended up buying vintage ones (made by Effingham) for around $70 shipped. They were quite stiff and faded when I got them, which was remedied with some coats of simple boot wax; now they are quite comfortable, even if they hug my calf. Shortly after they arrived, I made sure to get a boot jack, as my initial experience of taking them off was quite nerve-wracking. I don’t want to throw out my back whenever I take off my glorious boots. 

Now, even though the real draw of these boots has been the general LARP connotations, I’ve actually only done that type of fit twice: a Star Wars-esque fit for Nerf and to this year’s Ren Faire (in which the boots really helped sell the fit. But that doesn’t mean my Riding Boots have been in my closet collecting dust. In fact, it’s been quite the opposite— I’ve worn them surprisingly often, especially in the weeks before the weather warmed up.

As you likely expected, all of the outfits that utilized the Riding Boots have been quite Apparel Arts or at least in that midcentury Anglo-Americana way. Think tweed jackets, OCBDs, Barbours, and flannels. These are all things I wear regularly but the addition of Riding Boots leans further into a niche POV!  With these boots s, my outfits [hopefully] read more Cecil B. DeMille, aviator, tailored archaeologist, or simply a semi-sports country guy (in the classic menswear sense) who dedicedly rides horses and has just finished playing a jaunty game of polo. It’s trad, slouchy, and leisurely while still being a bit more trussed up than my beloved dainty tassel loafer. 

This effect is all due to the tall shaft of the Boot, which I emphasize by tucking my trouser hems into them. Admittedly, this is a bit of a silly move, as jodhpurs or breeches (in cotton or wool) are the correct pants to wear with Riding Boots as they fasten around the knee, ensuring a clean tuck into the boot. I don’t own those pants (not yet anyway) but my workaround has been to simply wear my slimmest trousers: I have two pairs of straight-leg western chinos as well as one thrifted pair of grey flannels, all of which have worked wonderfully, even if I have to end up having to press my pants after each wear. 

Of course, in true Ethan fashion, I ended up sourcing some proper riding pants (ahem, jodhpurs) a few weeks after I wrote the previous paragraph. The ones I got are from the 60s and are made of a cream nylon-rayon fabric with brown suede in the knee area. They don’t “balloon out” as much as traditional riding pants which helps them feel a bit more wearable (I wouldn’t have minded if they did) and come across as more streamlined, perhaps a bit feminine, which I enjoy.

Whether it’s tucking in my pant hems or wearing proper jodhpurs, the resultant look is quite different from my usual attitude. I think both moves help to sell the effect of Riding Boots and allow me to lean further into the theme, as well as create a fun proportional result. I’d even say that this helps me “reference” (ever so slightly) the zeitgeist’s hesitant return to slimmer silhouettes without me adjusting the width of my preferred trousers (which I would never do). Overall, it has been fun to take a break from the wide-width and shivering-break hems you typically see me wear, but in a different way that explores a new and nuanced POV.

I really do enjoy wearing my Riding Boots. They’re just a great way to lean into a vintage menswear POV, apart from simply wearing the associated proportions or particular shirt collars, tie patterns, and hats. The Boots also just help scream fall and early spring in a different but similar way that White Bucks and Sandals do for general spring/summer.  And to my surprise, I find them quite easy and natural to wear, as out of place and bold as they are. The boots (and the resultant look) are definitely a dandy and foppish move (I ain’t escaping those accusations), but I don’t mind it. I think it makes sense for me, especially when you consider my cosplay allegiances.

Riding Boots just say a lot more than the agnostic (but similarly rugged-meets-trad) chukka boot or commando sole derby. Hiking boots might do a related POV, but they are a bit too chunky; cowboy boots turn everything Western, even if the horse connotations are present.  It’s hard not to bring Cowboy boots to mind as they are extremely expressive and have a light horse connotation, as wearing them does indeed coat your outfit in casual light, leaving it up to you to decide if you want to subvert or lean into the vibe….that is decidedly Western. I might want to have that casual vib,e I don’t necessarily always want to have a cowboy vibe.

Menswear isn’t about formal vs. casual but about dressing to express the POV or character that you want. They’re specialized and are definitely rooted in a particular part of classic menswear, even if they go with everything. They’re a bold choice but still feel refined. It’s camp and certainly flamboyant.  I’m not saying you should get them for yourself (as they are difficult to find), but I like them. I think it’s safe to say that they’re a firm part of the Ethan Canon at this point. When it comes to new things or experimenting, I tend not to buy it unless I am confident that I’m going to wear it often (and easily). 

Clearly, these boots are the most costume-y thing I own. Granted, a lot of classic/vintage menswear falls that way too but there is still a bit of practicality involved: fedoras shield against the elements, and kimono coats are a layering piece that remains quite comfortable and easy to throw on. Riding Boots are a bit out of left field for a practical menswear guy, even if they are footwear and are rooted in menswear history.  

But I’m not practical. I’m an absurd person. I love wearing ties when I really have no rhyme or reason for them. I could get away with one solid knit, but that’s not me. I like the patterns and expressive merit that each of my ties brings to my outfits; making a pleasing combination is what keeps menswear so interesting to me.  I don’t own them for practicality, I own them because I love them. Should Riding Boots be any different? 

The only way these would be a waste would be if I never do a Luke or Han Solo look. You guys will have to hold me to that. 

Just please don’t ask me if I know how to ride a horse. The answer is obviously no. And yes, I’ve already gotten that question asked of me a few times when I’ve worn my beloved riding boots (and pants) around town. I guess I really am poseur!

– end of blog post –

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Always a pleasure,

Ethan M. Wong (follow me on IG)

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