Stake Out: SPY’s Street Style Report

Al is making denim-on-denim work well into the fall with a Levi’s vest and shorts, paired with Clark’s Wallabees.

Jah is making old things new again. He’s got a vintage tuxedo shirt refitted for summer, paired with Dickie’s that he’s repaired and patched himself, and Veja sneakers.

Brendan has a white J. Crew suit with a Club Monaco shirt, ready to squeeze the last days out of the summer.

Reynaldo’s suit and shirt come from SuitSupply, but the hat is straight from a Ralph Lauren’s own roastery.

Chris’s is making this CDG shirt his own by misbuttoning it, and its paired with Wales Bonner Adidas sneakers.

Ky’s got a vintage Balenciaga shirt and Needles pants on for a baggy fit ready for Fall.

This guy’s wearing a Zegna red blazer, incotex pants, Hermes belt, ferragamo driving loafers.

Donovan’s got on a bespoke jacket dating back to the 80s, pants from Ralph Lauren’s Purple Label, and slippers from the Stubbs and Wooton J Press collab.

Nick is wearing a vintage US Marines shirt jacket, OrSlow denim pants, and Soloviere shoes.

Ebrima’s Ben Davis painters overalls and Troentorp Clogs are a force to be reckoned with this Fall.

Reggie’s got a Todd Snyder shirt and jeans paired with Belgian loafers.

Kshitij is wearing a vintage sweater vest with Levi’s jeans and Alden shoes.

Yung Chomsky is sporting a Scott Fraser Collection shirt, Nepenthes belt, and vintage trousers.

Manny is decked out in all vintage pieces, with yellow Chuck Taylor’s and an RRL shirt.

Frankie’s making the most of the last days of summer with the Cranbrook hat from Arcteryx, Dita sunglasses, and shoes from the Gucci x Adidas collab.

Jackson’s all-black ensemble is landing on the right side of the downtowner style. His Vans slip ons pair well with the Midnight Rodeo duo he’s got: tee shirt and sunglasses from the Thierry Lasry collab.

Rowan is pairing a custom-made trucker jacket by Calvin Klein with pleated pants from Acne Studios.

Adam’s nailed the summer preppy in the city vibe here. His Alden loafers and Levi’s jeans are the perfect pair to match a Filson bag.

Vinny’s style is a perfect blend of timeless and nuanced looks. Issey Miyake pants with Vans sneakers and a vintage tee are a cap-tip to those in the know.

Angelo’s vintage Friends tee goes well with his Army surplus store pants and Nike SB Dunks.

All of Mark’s wardrobe comes straight from RRL, from jacket to pants. The one outlier is his pair of Wallaby’s from Clarks.

Jordan’s got a navy blue jersey from one of the top-tier street style brand collabs: Comme des Garcons x Bape.

Donny’s wearing pants and flip flops both from Marni. His Tom Ford sunnies are also working overtime through the heat wave.

For a more summery look, Tommaso’s got Belgian suede slippers, trousers from Pommella, and a J. Mueser seersucker shirt.

Angel has a Banana Republic suit paired with a Ralph Lauren oxford shirt and loafers from Cole Haan.

Kwami thrifted this sweater vest from Forever 21 and paired it with Dickies shorts.

Liam is matching basics with luxe goods: Persol sunnies, shirt and cargo pants from Dave’s New York, and Solovair boots.

Justin’s wearing pants from Canceled and Birkenstock Arizona shoes.

Dimitri is sporting pants, shoes and a shirt from Dries Van Noten, along with a bag from Want les Essentials.

Michael has Vans Slip-ons, an LL Bean Bote and Tote, and a similar Brut Re-Work jacket.

For a more polished, Upper East Side sensibility, Mark is wearing a Paul Stuart blazer, khakis, and Alden loafers.

Light jeans work all through the summer. Stephon’s are from Todd Snyder’s relaxed fit denim line. He’s pairing it with a shirt from The Armoury and vintage loafers and vest.

Harry is wearing A Vontade jeans, Grandma’s Vintage London Fog harrington jacket, and a hand-cropped tank. Mel is sporting Made in England Doc Martens and a tote bag by Colbo.

Ali is wearing a shirt by Sacai, pants from Banana Republic, and Feit shoes.

Brian’s wearing Rubinacci Belgian loafers, a knit tie from the Andover shop, a Todd Snyder western belt, and a hat from Raoul’s.

Paris is wearing sunglasses by Ray-Ban, Crockett and Jones loafers, and a Sartorio Napoli blazer.

Christian’s wearing shorts by Silphium, Salomon hiking boots, and an Ireland tourist hat.

Mitchell’s mastered preppy-style with simple picks like a Ben Davis tee, Lee jeans, and Luchesse boots that perfectly matched a very good boy.

The blues look good on Michael, with a Reigning Champ crewneck and Levi’s jeans, paired with some New Balance sneakers.

Wayne’s look works from the office to the afterparty. A DB jacket from Suitsupply and and Maison Martin Margiela German Army Trainers are brought together seamlessly by his Jacques Marie Mage sunglasses.

Sporting a Loro Piana suit and Alden Cordovan tassel loafers, Chris pairs it down nicely with a simple white henley.

Don’t look at the thermometer, Michael’s primed for the chilly summer nights in the Hamptons as far as we’re concerned. That’s why he’s got the Nanushka sweater paired with the Nanushka pants for a combo look.

Jon’s leaning into layers for summer with Dickie’s overalls topped with an LL Bean chamois shirt.

Rainstorms come out of nowhere lately, which is why Edwin’s prepared with a Goldwin shell jacket.

Ping-Pong’s keeping cool in the heat with Gucci loafers, Levi’s, and Oliver People’s sunglasses.

Alex is bringing some colorful looks to the streets with an Issey Miyak jacket and pants. He’s also keeping it casual with MIHARAYASUHIRO shoes.

Standing outside The Armoury in Tribeca, Matthew has mastered Ivy Prep for the summer with a bespoke blazer from Tailor Caid and saddle shoes with a repp tie.

Extra-wide trousers aren’t merely coming back, they’re here. Dubois’s pair from OAS adds some height to this look without pulling too much away from the vintage sweater.

Will has mastered the look for a walk around the Central Park sailboat pond: belgian shoes, Sugar Cane jeans, and a blazer from Ring Jacket.

It’s a summer built for Brooklyn thrifting. Denny’s got the pairing down right by mixing tailored pieces like this vintage Brooks Brothers shirt with an oversized Utah Jazz jacket and wrangler jean shorts. The tasseled loafers add a dash of prep too to bring the whole look up a level.

Baggy trousers come in all styles. Cade’s cargo options from EighteenEast are well contrasted by a breton striped shirt and Braindead sunglasses.

When you’ve got the statement shirt in place, like this one from Bode, you keep everything else simple. For Jordan, that’s some Bottega Veneta shoes and a tote from Want Les Essentials.

It’s too hot outside to not keep it casual. For Will, that means Issey Miyake shorts and sneakers from Loewe to hit the streets.

Naoki’s two-way white tee from Blue in Green is taking this look back to (elevated) basics with Red Kap carpenter jeans and wallabee boots from Padmore and Barnes.

Weekends are for well dressed dudes just hanging out. What goes better with an Engineered Garments Loiter jacket? Your friend wearing some Ekhaus Latta baggy jeans.

Keep it simple, and then dress it up at the end for a little preppy pop. For Dwane, pairing the orange of this Polo Ralph Lauren cricket vest to the stripes in his Adidas Superstars makes all the difference.

All black always looks great in the downtown scene. Carlo’s making a case for it with Tom Ford sunglasses and a jacket from Alyx.

The majorette blue French blue chore coat Jeff is wearing is a vintage find, but there are plenty of similar options available—like this one from Wolf & Badger. To schlep around all his stuff, he’s got a Filson tote and wearing New Balance 574 sneakers to get him around town.

Too often, the ample storage of winter coats lead to feeling strapped for places to put your stuff when the weather gets warmer. Instead of opting for backpacks and messenger bags, pop on a Columbia Fly Fishing Vest and have everything tucked safely away. To really lean into the granola-chic style trend, add a pair of Birkenstock Boston clogs. 

Yun Soo’s classic New England look is working from top to toe: Barbour Bedale jacket, SNS Herning Cardigan, and the Aurora Shoe Co. collaboration for Drake’s. This is the look of someone who’s never far from a boat, and definitely has sweaters with “school colors.”

Just because a baggy-chic wave has hit mens pants, doesn’t mean everything needs to sag. This suede Todd Snyder jacket creates a streamlined, tailored look that highlights trendy style picks like looser vintage military pants.

Just because things come in a matched set doesn’t mean they can’t live separate lives. For example, Justin’s Uniqlo U pleated trousers look great with with Asics Sneakers by Kiko Kostadinov.

Some looks start from the ground up. Sky blue penny loafers from Camper are a big visual pop that lead to vintage trousers from Comme des Garcons and a vintage linen jacket.

Smoking isn’t cool, but it’s not our fault that vintage cigarette t shirts like the one Maetha’s wearing kind of are. He’s paired it with Acne Jeans and sunglasses from Jacquemus, finding the right balance of fashion kid and punk rock.

I suppose you need something extra reflective when you’re on the high seas, like these Pit Viper sunglasses. But hey, keeping a uniform that pristine and white with NYC soot and grime all over the place is no easy task.

It’s time to get behind the vest. For a relatively low amount of heat added during summertime, the additional layer, like this one from Skunkworks, offers four additional pockets. The J. Press seersucker popover shirt also gives the look some contrasting, pastel colors with more formality than a white t shirt.

For more slender frames—like Dominic—opting for a baggier look can be tricks, so that the clothes aren’t wearing the man. In this case, extra wide shorts from Colbo, and a wider-framed shirt from Hed Mayner are balanced by slimmed down Lemaire shoes and Jacques Marie Mage sunglasses.