A while back, I got a pair of wholecut leather sneakers from Beckett Simonon. I thought they looked kinda cool—they reminded me of Crown Northampton's, which I had wanted beforehand. But actually trying them out, I realized that, despite how ubiquitous minimal white leather sneakers were, how simple the wholecuts were, and how clean they could look in photos, the shoes were paradoxically hard to wear well.

Discussing this with menswear friends, some argued that wholecut oxfords were often similarly problematic. While people make some beautiful, sleek wholecut oxfords that show off an elegant last incredibly well in a vaccum, they usually look a lot worse in the context of an outfit. As the Styleforum debate on the topic of Oxfords worn casually rages on, it's clear that they're nowhere near as wearable as they might seem at a glance. And don't get me started on pre-patina'd shoes.

Now, you could go with a slightly more complex shoe. A german army trainer, a penny loafer, a longwing buck. Those generally look fine in most contexts. But something interesting happens when we take things to another extreme.

Chunky sneakers, Tyrolean Shoes, and Birkenstocks are all... Ugly. Just look at them. What dumb fucking shoes, right? Well... Until you put them into a decent outfit. Here's the other side of the paradox.

Themes to look for:

• Menswear enthusiasts sometimes like "ugly" clothing because it is ugly—because it presents a challenge to wear, or because it is interesting.
• The more "versatile" or "neutral" a shoe is, the less it contributes to an outfit. A totally versatile shoe like a white leather sneaker looks bland with everything. An interesting shoe, while harder to pair, can actually look good.
• Oxfords are designed for wear with suits. Sleek lasts look "sharp," or "smooth," but clash with many casual vibes, including relaxed clothing, workwear, gorpcore, and milsurp. Good-ugly shoes may be "chunky"—their silhouettes might be wide, or high-profile, or angular, or otherwise unusual.
• You will also see lots of color, and lots of contrast.

Chunky Sneakers

In 2017, Balenciaga released a stupid sneaker. The Triple S is named for the way it crudely smashed three different types of sneaker soles together. The melted marshmallow vibes of the tall, ugly, chunky soles and bright, colorful upper bits haphazardly strewn about these Franken-shoes instantly made fashion history for being... cool as hell.

The Triple S is part of a recent trend, but chunky sneakers have a long, rich history. If you look in your dad's closet, you might find a par of dull gray New Balance sneakers. Its logo will be a big, ugly N. You'll wonder how your dad could have ever worn those hideous things.

But look at them in the right context, and they transform. New Balance 574s, 550s, and 99xs, in particular, are not just for dad vibes (usually in gray-focused colorways), but neo-Ivy, streetwear, and gorpcore as well. They each have their own heritage—particularly the 550, as a basketball sneaker. In comparison, 327s look like they're supposed to be prettier... and that's probably why they don't appeal to me at all.

But I love the "ugly" new balances. They strike me as an easy shoe to wear—even compared to my white sneakers. Again, I've tried my white sneakers in a lot of combinations, and they don't look awful, but they never really made me happy, they never really looked good, always like I was trying to get away with owning as few sneakers as possible.

But New Balances say something next to jeans, next to sweatpants, next to chinos, next to tailoring, and all of those things make sense to me. Dadcore done right, streetwear easy mode, neo-ivy, menswear merger. They make boring styles interesting, and interesting styles accessible. Even one odd-colored pair can do what the white sneakers try and fail to accomplish: they span a spectrum of styles and shine through them all.

Another absolute classic, even if it is controversial, the Fila Disruptor is known for an exceptionally thick sole, but also for its white colorway. In a profile on the shoes. Chris Black called them “an ugly blemish on our beautiful world,” and Lawrence Schlossman, “a crime against good taste everywhere." I agree that they are ugly, but are they good ugly? I've certainly seen women pull them off. I believe they look better-proportioned on small feet: shorter and narrower, but still with the high profile sole, the part that needs to shine.

Aside from the Disruptors, and gray New Balance sneakers, these chunky sneakers also tend to feature complex color patterns. New Balance isn't shy about color. Personally, I'm partial to Karhu's colorways. I find New Balances exciting on paper but hard to pair; Karhu's colorways are more... harmonious—even some of the more interesting colorways can fit nicely with a variety of outfits.

Brands to Consider:

• New Balance 574 (alt link)
• New Balance 990v3, 992, NBxALD 993, 997h (alt links to 990v3, 992, 993, 997h)
• New Balance 550 (alt link), NB x ALD 550
• Fila Disruptor II
• Karhu Fusion 2.0
• Salomon Raid Wind Advanced (alt link)
• Asics (alt link)
• Saucony (alt link)
• Buttero ($25 off referral link) (alt link)
• Diadora
• Moncler "Leave No Trace" (alt link)
• Balenciaga (alt link)

Tyrolean Shoes

Tyrolean shoes are weird. On one level, they're kind of like moc toe bluchers... if the moccasin went all the way around to the relatively small lacing system, relatively high on the shoe. But the real oddity is not the moccasin-esque seam itself, but the way the upper turns in and up and out. They have a sort of upside-down and backwards feel.

The whole setup is bulky, even compared to a moccasin-lasted loafer or a chunky blucher. And because it involves two very distinct pieces of leather, it lends itself to unusual two-tone makeups. The close, short lacing system can draw some interest with chunky laces, or with alternative takes like buckles.

I saw a lot of well-dressed men wear Tyrolean shoes, and they never looked right for me—maybe just because I wasn't used to the idea. I don't think I really understood them until I saw Eric's two-tone Paraboots below.

So these funny-looking shoes... are interesting. So menswear guys love them. They add a little weight at the feet, but also give you new details to look at. The stitching, the last, the lacing... they're all something fresh and new to look at, not your boring old plain toe derbies.

The chunkiness can contrast nicely with a suit, without going so far as a colorful pair of New Balance sneakers. They work great with jeans, in gorpcore, in bookcore... It doesn't hurt that they're a hundred years old, because they've somehow flown under the radar until recent years, and even still have that insider charm.

And if you do have a complex two-tone makeup, like Eric's comfy-looking pair above, then you've got twice as many textures to show off. And unlike, say, spectator wingtips, they don't carry stuffy old associations—they're unusual enough to feel new and cool.

Brands to Consider:

• Clark's Wallabees (alt link), in a pretty squared-off last Note the funky paisley velvet models.
• Astorflex Beenflex
• Padmore & Barnes makes a very low-vamp tyrolean shoe and tyrolean ankle boot.
• Kleman
• Paraboot Michael—a higher price than the above options, but a rounder and, in my opinion, much better last.
• Heschung Thuya. Get $25 off at No Man Walks Alone if you use my referral link. Or don't, whatever.

Kilted Shoes

We can all agree that kilts are ugly, right? A few odd strips of leather, cut sharp, lined up in a row... slowly curling up and away from the shoe... Whose idea was that? Kilted shoes (or "kiltie shoes" if you want to make them to sound cute and stupid) look like somebody just had too much leather lying around, and wanted something to do with the straps. And for some reason, the "tongue" on kilted loafers is often squared off.

Well, once again, a terrible idea turned out to work out just right, because a kilt is just the right bit of interest some outfits need. I associate the style with loafers, although, as you'll see, that's not an exclusive combination.

The kilted tassel loafers from Solovair and chenjingkai office, in particular, have a lug sole, and that gives them a certain charm. Lug sole loafers in general are interesting—Blackstock & Weber and FE Castleberry have some cool models—but they aren't stupid enough to put a kilt on a shoe they want to sell. Yet.

Yuketen—oh boy, I have so much to say about Yuketen—makes a particularly ridiculous tassel blucher. What? Kilted camp moc bluchers, I didn't even know that was an option.

Brands to Consider:

• Solovair Kilted Tassel Loafers
• chengjingkai office kilted tassel loafers
• Yuketen Kilted Bluchers with a crazy thick sole.

Blundstones and other Chunky Chelsea Boots

I've mentioned wholecut chelsea boots before, and Blundstones are... pretty much wholecut. But unlike their smooth, sleek siblings, Blundstone boots are chunky. Their materials are rustic, drab, unpolished—treated for water resistance or other technical properties rather than a sleek consistency.

Their rustic look helps give men ease of mind. Blundstones fill the slot of a rugged boot. The men who wear them wear them in the rain, or even the mud, with denim and flannels. An SLP Chelsea boot and skinny jeans feel precious, but chunky blundstones and bootcut raws give rise to that key nonchalance—visible comfort.

I've generally resisted them, myself, as I never thought of my own style as "rugged." But ultimately, I need a rugged boot for snow and salt and mud, and I think Blundstones will probably end up serving that role better than anything else for me. I wouldn't wear them with any suit I can think of now, but I'll wear them with jeans and chinos and it'll work.

Brands to Consider:

• Blundstone
• J. Crew Kenton on deep sale—definitely under $150, possibly under $100.
• Red Wing

Clogs

If you go looking for menswear "rules," you'll invariably start noticing a few that are obviously ridiculous. Some men will say you should never wear shorts. Another rule suggests that wearing brown shoes in a city is somehow a bad thing. And many of these stuffy old coots will argue that men should never wear open-toed shoes or sandals. Utterly Ridiculous.

Luckily, the utterly ridiculous is familiar territory for us by now. Instead of asking why backless slip-on shoes really need buckles, we just laugh about the fact that a brand that used to be known for a stereotype is now hyped to hell for straight men too.

The stereotype primarily refers to the Arizona, but I don't think the Arizona is really ugly. If you accept that open-toed sandals are wearable, the Arizona is probably about as pretty as they get, at least for men.

But the Boston—and clogs in general—kind of have a certain ugliness about them. They're a smooth curve, but that kind of clashes with the cork sole to remind you that what you're looking at is still at least kind of a sandal. They still remind some of a stereotype, and they still have a buckle for some now-inexplicable reason, and the upper is cut funny to accomodate the strap. You see them in oiled leather and suede, in plain, somewhat wide-looking lasts, and they kind of just look... blech.

Until you pair them just right. And then they start to fit Nepenthes styles, TF-core, gardencore, sleep vibes, crunchy hippie vibes... And yes, in some cases, high fashion styling. If you really want to, yes, wear them with socks. Is it garish? Yes. You should know by now that that shouldn't stop you.

Note that I won't be recommending crocs, no matter how popular they become. Crocs are for nurses and bakers and that's about it. I draw the line somewhere.

Brands to Consider:

• Birkenstock Boston
• Yuketen Sal 1
• If you must get a rubber clog, the Garden Heir "Italian Garden Clogs" are... well, something

Tabi Boots

Hah, just playing, Tabi boots are dumb.

Split Toes

This is a subtle one. Split toes—including "NSTs" or Norweigan Split Toes—have always irked me. Moc-toe stitching is already a little bit rustic, but dropping that tiny line straight down the front of the shoe... it might seem like a small detail, but it doesn't add anything good. All it does is interrupt the smooth curve. That's dumb.

And that's what makes people like them. That subtle little line... kind of ruins these shoes in exactly the right way. It's hard to explain just what's right about split toes, but the extra bit of exposed stitching just adds that extra bit of rustic charm. It draws attention to the toe, and to the symmetry—or asymmetry—of the shoe. And it just feels a teensy bit more... rugged, for some reason. At least, that's what I see.

Brands to Consider:

• Meermin
• Paraboot Avignon
• Heschung Thuya, a split-toe Tyrolean shoe.
• Alden has about forty different split toe models sold through like 4,000 different dealers, go pick one.
• Drake's x Edward Green

Hiking Boots

Hiking boots are a funny thing. I'm not sure if people really wear them hiking, but the style is... Weirdly close to a wholecut boot, but with a chunky sort of tongue-thing, similar detailing around the top of the ankle, but most noticeably, an unusual lacing system. Thick laces, perhaps made with bungee cord, loop through speed hooks up top, but also metal... doohickeys in place of eyelets along the body. Since these doohickeys sit on top of the shoe, the entire thick lacing system is very visible and dominates the top of the shoe.

In some proportions, they might still look simple, or even clean, but they still jive with rugged practicality. Leon wears them below with a cotton-looking suit and simple color scheme, and they look clean; he adds a crunchy vest layer, and they seem even more at home, like he could go for a hike through... the nearest city park, at least, and be right at home.

If you keep an eye out, you'll occasionally see sneakers with hiking-boot-inspired lacing. These came out of the gorpcore wave, but while gorpcore peaked, hiker-sneakers seem to be sticking around. Have fun with them.

Brands to Consider:

• Sorel Hiker Boots (alt link)
• J. Crew low-top hiking boot, with more of the ugly sneaker vibes from above than the leathe options on this list.
• Danner x Jjjjound Mountain Hiking Boots
• Paraboot Avoriaz
• Fracap's Magnifico M120 and M130 are customizable.
• Diemme. Also, Diemme x J. Crew
• Viberg Hiker

Duck Boots / Bean Boots

In the case of some of the shoes above, you guys might be thinking, "I don't know, those don't really seem so ugly to me." Well, I've got the style that will shut you up. Bean boots are... pug-fugly. They look like somebody took one ugly boot, and wrapped the bottom half in a different, even uglier rubber boot with a bunch of vertical ridges. They were made in an extreme case of function over form, handling the elements better than anything, but that doesn't stop people from seeing some sick, twisted beauty in a well-worn pair.

Bean boots have gained some favoritism among enthusiasts. Not only because they're cheap and impervious to all external forces, but because of the way they fit into the relevant vibes. Casual ivy and gorpcore each appreciate them—the former because they have a long history of being worn by cheap college students at fancy colleges, and the latter because they're chunky and because they exude the crude practicality they actually serve.

Personally, I was introduced to them as a shoe nobody wore for style, but only for handling snow and mud and rain and sleet. When I first discovered that people wore them for style, I had a somewhat visceral reaction. But, aside from the Ivy folks wearing them purely for hsitory... That's it, the visceral ugliness is the charm. The idea that anybody could ever wear such a clunky, function-forward malformed mess well, to dress like you're about to trudge through the mud, but make it fashion... It's an extreme form of everything in this article.

And then of course, some brands like Diemme put out more fashion-forward takes, and although that's a very different story, I think they still capture much of the same ugliness.

Brands to Consider:

• L.L. Bean - Bean Boots (alt link)
• Sorel Cheyanne (alt link)
• Studio Nicholson
• Diemme duck chelseas and laced duck boots

And pretty much anything else from Yuketen

Seriously, just any of it. Megco—the company behind Monitaly, Yuketen, Chamula and Epperson Mountaineering—gets "good ugly," but... thick-soled moccasins with an extra horizontal layer of contrast on the lower portion... Two-tone wingtip boots with a superfluous strap and buckle on top of the laces... these weird boots. Their designers are swimming in a pool of spice melange. They're tripping their way to a higher consciousness.

Conclusion

I'm certainly not against beautiful footwear. I still love my oxfords and my sleek wholecut chelseas, and Feit makes minimal and wholecut sneakers that escape the curse.

But I've learned some lessons. I've learned not to judge footwear based on the appearance of the shoe itself in photos, but to think a little bit deeper about how it will work in an outfit.

And I've learned to appreciate a little more complexity in shoes. Instead of exclusively going for sleek, simple and apparently versatile or dressy options, I am going to keep an open mind to chunky soles, funky colors, unusual lasts, and other details I didn't always like.

I usued to find minimal white sneakers and slippers / wholecut loafers more appealing, but now, I'm a little more skeptical. I decided that heavily patina'd and overly sculpted oxfords aren't for me a while back, but I realized that they might not look great with my slim chinos or my jeans.

So as with a lot of my articles, my core recommendation ends up being to keep an open mind. You don't need to go buy shoes you think are ugly, and you don't need to stop buying chelseas and oxfords. Just think twice about what makes a shoe good. Try a shoe on, imagine what you're going to pair it with, and consider what it adds to an outfit, instead of just assuming that a pretty shoe in the window is going to look right in your outfit, or that a strange, chunky mess is going to look bad. It might, but that second thought could surprise you.

Additional Reading

• Ugly Shoes That Are Actually Kind Of Great - Put This On. I swear, I only found this article after mine was mostly done.
• Bookcore: How Everyone Is Dressing Like a Bookstore Regular - Die, Workwear!
• Styleforum threads on oxfords worn casually and fancy dress shoes with fancy jeans, both expressing the limitations of fancy dress shoes.
• /r/moresneakers

Let me know if you want to see an anti-inspo album for oxfords, white sneakers, or some other pretty shoes.