The Flyest Shoes in Fashion Right Now All Cost Less Than $200

Five NYC fashion insiders talk about the power of regular footwear.

A few weeks ago, as I exited a meeting at the GQ offices, I was joined in the hallway by senior editor Noah Johnson and deputy style editor Sam Schube. Most of us on the GQ fashion beat have our own little style lanes carved out, but in a minor Condé Nast faux pas, we had all left the house with the same shoes on: Blundstone 500s. (If three’s a trend, just wait: Fashion editor Jon Tietz cruised by in his own pair shortly thereafter.)

With any other shoe, the style mind-meld might have been unsurprising. But Blundstones are the un-sexiest Chelsea boots in the fashion universe. The pride of Tasmania for over 100 years, Blundstone’s signature product has a clunky round toe, treaded sole, and rubbery leather—the quintessential gardening boot, basically. But this winter, the 500 hopped the L train turnstile and flooded streets where not too long ago the razor-sharp Hedi Slimane–style Chelsea reigned supreme. (As much as I would like to say we willed the trend into existence, I hesitate to assign that much influence to our only B’stone plug back in January 2017.)

New York’s recent garbage weather is one reason Blundstones usurped dressier boots in my personal rotation, but I wear them on nice days, too. I’ve simply come to love their abundant regularness. Clocking in at $175 at retail (but easily found for less), they’re the most democratic Chelseas out there that look awesome with every pair of weird pants I bought last year. And these days, you’ll see similar style moves on men all over NYC (or at least near the Clout Corridor and Dimes Square)—guys who won’t blink at designer pants or a $1,000 coat but are true believers in the power of simple, sensible shoes. I decided to talk to some of them, below, about the go-to regular footwear they reach for in the era of teched-out sneakers: Blundstones, Wallabees, New Balance 990s, Dr. Martens, and Bass Weejuns.

Is it a simple swing of the trendulum that’s turned reliable shoes into desirable ones? The footwear listed above certainly represent an antidote to the hype fatigue brought on by the endless waves of chunky high fashion sneakers and impossible-to-cop collaborations. But there’s also been an undercurrent of influence that’s made anti-fashion the cutting edge. The unlikely men’s style hero of our time is, of course, Shia Labeouf, who wears tattered sweat shorts with army surplus combat boots and crocs. (Shia’s style is said to influence Kanye’s Yeezy line—regular footwear is an essential part of Erewhon Drip.) It’s created the perfect opening for the classics to grow into, like the ultra-normie New Balance 990, which fits right into the era of expensive graphic tees and high-end carpenter jeans. And take the Clarks Wallabee, associated with British Mods, Jamaican reggae, and Wu Tang. Today the Wallabee is a hot shoe at the intersection of high fashion and streetwear when guys who guide the culture, like Angelo Baque and Tremaine Emory, wear them. Not to mention the walls between traditional style tribes have never been more porous. As Noah sells rugby shirts to downtown kids, skaters crushing beers at Sophie’s are wearing loafers and socks with their slashed Dickie’s. The shoes your parents forced you in as a child—or you purchased during your punk phase, like Dr. Martens—are now available to everyone.

Every bottoms-up trend gets co-opted by the capital-F fashion world at some point. Rick Owens just dropped a furry and expensive Birkenstocks collab. Balenciaga made an infamous towering croc. Uggs has looked to Y/Project and even Heron Preston for some much needed juice. But the best regular footwear has remained relatively unspoiled. That is, there’s no reason you’d want to buy the designer version of any of these. Meet some of the guys who do the originals well.

Shoe of Choice: Bass Weejuns ($110)

AKA @donetodeath, Chris is a partner at Public Announcement.

Origin Story
The reason I’m so attracted to Weejuns is ’cause I wore them as a kid. I obviously rebelled from them for years and years, and then six or seven years ago I got a pair again, and now I wear them every day. For $100, if you take care of them, they’ll last forever. I’ve seriously had the same pair for seven years. They’re classic and can’t really be fucked up. That is eternally appealing.

Luxury Version: Y/N?
There’s always that pull I feel to buy something very expensive, that J.M. Weston or John Lobb, and every time I get close to it I’m like, why? It’ll take me a year to break them in and they cost literally $1,000.

Pennies or No Pennies?
I keep pennies in them, I keep it real. The other key to Weejuns is to get them polished all the time. It keeps them looking very good and more expensive than they are.

Frequency in Rotation
Four to five days a week.

Styling Move
I wear them with jeans, Dickies, and Patagonia Baggies. Even for walking around. They’re not that good for your feet, but I’ve just gotten used to it. I love the way they look, so I’m willing to risk it all to walk around Manhattan in the Weejuns.

Shoe of Choice: New Balance 990 ($174.99)

Lawrence is Grailed’s brand director and co-hosts the podcast Failing Upwards.

Origin Story
I’ve probably been wearing New Balances for the past four years, and then in the past two years I’ve really fallen in love with the 990 for a variety of reasons, from a utilitarian standpoint to just appreciating them aesthetically. The grey 990 is what my dad has been wearing for ten years at this point. There’ve been a few moments when I’ve worn my 990s to see my parents and my dad’s been loving it. Right now he wears destroyed Carharrts and 990s, which funnily enough has become the de facto cool guy Brooklyn uniform.

Favorite Iteration
The ultimate best is the grey. But my favorite that ever came out was the Stussy collab, which I don’t have a pair of, but it’s that perfect off-white color that you can’t just get from New Balance. But the one you buy, you buy the grey.

Why the 990?
I want the dad shoe look, I want the tech comfort, and the 990 is the middle ground between the really basic shit you might buy at J. Crew that I don’t want, and the crazy chunky stuff like the 999. The 990 checks every box.

Frequency in Rotation
I have so much fucking footwear ’cause I just love sneakers and shoes and loafers. I probably wear them once a week, but that’s saying a lot. I have the Off-White Air Max 90s, and I never wear them. I wear my New Balances more than objectively more hyped sneakers.

Styling Move
I love the 990 silhouette aesthetically because it looks good with looser and wider-fit pants. I have on Supreme dad jeans today, but I’ll wear them with my Engineered Garments cargoes, or Lemaire trousers. That little bit of break and wider opening on top of the 990s just really does it for me. Prior to me wearing pants like that, it was a shoe I thought looked really good with shorts. So I also wear them with Baggies.

Value Proposition
$175 is a lot, but at the end of the day what goes into it is truly worth it. If New Balancess were re-selling for Wave Runner prices, that would be different, but because you can just get them, I’m personally willing to pay that little bit more rather than buy a general release sneaker from another brand for $150 or whatever. You get a ton of bang for your buck. New Balances aren’t made so you can flex on IG, they’re made so you can walk a shitton.

Shoe of Choice: Blundstone 500 ($174.95)

Jon is a GQ fashion editor.

Origin Story
We had a hobby farm in Wisconsin growing up and that’s when the Blunnies went down. My middle brother’s style has always been very utilitarian and chill, and he got them first. They were perfect for the farm—you just slide in and rock ’n’ roll when you need to run out the door.

Design Appeal
There’s nothing bad about how they look, there’s nothing good about how they look, they are what they are. They’re almost minimalist. There’s nothing about the design to take away. And the raddest part of them is that they’re basically unisex. As Chelsea boots are getting phased out a little bit, the husky utilitarian unisex boot is huge.

History Lesson
They’re to Australia what Red Wing was to the US.

Frequency in Rotation
I leave a pair at my brother’s place upstate, and then I have a pair in the city. I wear them whether it’s shitty out or not, because your feet still breathe in them.

Styling Moves
I usually wear them with a wider-leg pant, but I’m most excited to wear them with shorts this summer.

Shoe of Choice: Clarks Wallabee ($135)

After ten years at Supreme, Angelo is now a creative consultant and designer of red-hot streetwear label Awake NY.

Origin Story
I’ve been wearing Wallabees since 2000, 2001. When I got my job at Stussy I saw James [Jebbia] with Wallys on. I knew Wallabees were in the culture, but I never saw someone wear it on the day to day like that like James.

NYC Connection
I grew up in a West Indian neighborhood in Queens, so I grew up watching the older, cooler West Indian cats wearing Wallabees. So it’s always something I connect to being from New York and coming from a Trinidadian/Guyanese neighborhood that I always found really cool. It’s a very New York thing. Besides connecting back to the highlands of Jamaica, it’s very Wu Tang: it’s Raekwon, it’s Ghostface.

Designer Version: Y/N?
Hell no.

The Youth
When I bring younger kids to my office, they trip out that I got Wallabees—in a good way. They’re like, yo, those are fresh. ’Cause I don’t think their age group is really checking for Wallabees right now. It’s definitely my age group: Chris Gibbs, Tremaine [Emory], the older cats that grew up on this. We’re like, this is where we came from, this is culturally relevant to us today. As it was in ’94, or ’99 or 2000.

Frequency in Rotation
I wear them 50% of the week I’d say. They’re my equivalent to a pair of Chucks.

Styling Move
Honestly I can wear them with anything. Jeans, Comme des Garçons pants, wide-leg Dickies, even shorts. I love wearing them with shorts. And I wear them barefoot when I can.

Number in Closet
I have close to 20 pairs, always low top, all in the same color: fudge.

Shoe of Choice: Dr. Martens ($185)

Mac is an all-star stylist whose work has appeared in W, Interview, VMAN, and many more.

Origin Story
I got my first pair when I was 11 or 12, so in the early-’90s. I grew up skateboarding and listening to hip-hop, and then obviously Nirvana came around. So it was that era, and I remember seeing Dr. Martens. I must have gotten them for a birthday or Christmas. I’ve kind of gone in and out since then—I wear ’em, then I put ’em away, then I come back to ’em.

Preferred Model
Recently I got a pair of the red oxblood [1461] made in the U.K. ones. I have the blue 6” boot, but the made in U.K. ones are so much nicer. They’re harder to break in, though.

Frequency in Rotation
I wear them a lot during the fall and winter. Once a week, maybe.

Styling Move
You can wear them with jeans, khakis, a suit. The goal is to dress in a way where you look at a picture of yourself in 10 years and don’t know when it was taken. I don’t want to dress with the times. And that shoe just hasn’t changed. You see a lot of what’s going on around us, and there’s a timestamp on it. So you stick to what you know: Levi’s 501, Dickie’s, Red Wing. I like things that work and are utilitarian.

Trend Advice
The trends come and go so fast and people dive into them so hard, but then they disappear just like that. You take the big fashion sneakers, you can tell people are going to get sick of that real quick and then you’re stuck with these expensive huge shoes. And when you wear the classics you kind of don’t have that problem. And they’re versatile—if you want to be a fashion guy, you can wear Docs. If you want to be a punk you can wear them.

EDITOR’S PICK