Stake Out: SPY’s Street Style Report


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Forget about the runways and look books. Some of the best minds in contemporary fashion aren’t hoisted up in the high rise offices of fashion houses, but on the street, roaming around with the masses. That’s why SPY’s man on the street has been documenting their style for an ongoing series of portraits ready to take right to the shopping cart.

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man in cool outfit nyc
man in cool outfit nyc

Buy the jacket $378.00

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Buy the trousers $Prices Vary

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Buy the tote $96.00

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Phillip’s got a blazer from Spier McKay, paired with a shirt and trousers from Proper Cloth, and a tote from Rowing Blazers.


man in suit in nyc
man in suit in nyc

Buy the suit $1,500.00

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Buy the boots $225.00

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Tim’s suit comes from The Armoury. He’s also wearing boots from Sanders and a zip folder from Boldrini.


man in cool outfit in nyc
man in cool outfit in nyc

Buy the Tamagotchi $40.94

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Buy the boots $425.00

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Buy the sunglasses $250.00

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Kyle’s got a necklace that features a Tamagotchi, Bottega boots, and Versace sunglasses.


man in cool outfit in nyc
man in cool outfit in nyc

Buy the pants $1,350.00

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Buy the watch $4,900.00

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Buy the bag $11,324.00

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Giuseppe is wearing pants by The Row pants, a Cartier tank, and carrying a Comme Des Garcons for Louis Vuitton bag.


man in cool outfit in nyc
man in cool outfit in nyc

Buy the shorts $Prices Vary

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David’s got a shirt that’s Gucci for Adidas. He’s pairing it with shorts by Bode.


man wearing cool outfit in a gallery in nyc
man wearing cool outfit in a gallery in nyc

Buy the look $Prices Vary

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Carl’s whole look comes straight from Wales Bonner.


man and woman in nyc wearing cool clothes
man and woman in nyc wearing cool clothes

Buy the coat $2,290.00

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The Armory Show was full of impressive style moves, none better than these two in full Thom Browne.


man in cool suit in nyc
man in cool suit in nyc

Buy the jacket $224.00

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Buy the sneakers $96.00

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Steve’s suit comes from Engineered Garments. The shoes are from Camper.


man in new york wearing dickies
man in new york wearing dickies

Buy the shirt $1,612.00

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Buy the pants $29.99

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Pieter—seen here in front of his own artwork—is wearing a shirt by Margiela, and Dickies pants.


man in nyc with jeans and boots
man in nyc with jeans and boots

Buy the jeans $450.00

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Buy the boots $575.00

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It’d only make sense that the guy at the Drake’s store was decked out in the Drake’s brand, right?


man in new york wearing denim on denim
man in new york wearing denim on denim

BUY THE VEST $18.97

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BUY THE SHOES $74.99

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


man wearing outfit in part in new york
man wearing outfit in part in new york

buy the shirt $148.00

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buy the pants $34.99

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buy the sneakers $127.00

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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.


man wearing suit on street of new york
man wearing suit on street of new york

buy the suit $158.99

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buy the shirt $69.00

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


man in a suit in new york
man in a suit in new york

buy the suit $859.00

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buy the hat $49.99

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


man in new york holding a beer
man in new york holding a beer

buy the shoes $284.00

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


person in new york drinking a beer
person in new york drinking a beer

buy the shirt $59.95

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buy the pants $260.00

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


two men walking down the street in new york
two men walking down the street in new york

buy the blazer $1,230.00

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buy the pants $385.00

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buy the belt $1,005.00

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buy the loafers $795.00

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


man in new york wearing pink blazer
man in new york wearing pink blazer

buy the pants $995.00

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buy the slippers $550.00

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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.


man inside a store in new york
man inside a store in new york

buy the jeans $330.00

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buy the shoes $355.23

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


person named ebrima in new york wearing overalls
person named ebrima in new york wearing overalls

buy the overalls $92.99

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buy the clogs $99.00

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


man named Reggie in new york wearing cool clothes
man named Reggie in new york wearing cool clothes

buy the shirt $298.00

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buy the jeans $198.00

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buy the loafers $675.00

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


man named Kshitij in new york wearing cool clothes
man named Kshitij in new york wearing cool clothes

buy the jeans $69.50

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buy the shoes $886.00

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


yung chomsky wearing cool clothes in new york
yung chomsky wearing cool clothes in new york

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


man named Manny in new york city
man named Manny in new york city

buy the shoes $85.00

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buy the tee $125.00

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


man in street of new york
man in street of new york

BUY THE HAT $80.00

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BUY THE SUNGLASSES $495.00

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BUY THE SHOES $3,350.00

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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.


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the shoes $65.00

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Buy the tee $Prices vary

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Buy the sunglasses $515.00

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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.


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the jacket $Prices vary

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Buy the pants $350.00

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


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the loafers $663.00

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Buy the jeans $79.50

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Buy Now $275.00

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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.


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the sneakers $59.95

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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.


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the dunks $353.00

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


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the jacket $290.00

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Buy the pants $345.00

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Buy the shoes $170.00

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


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the jersey $321.00

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


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the pants $441.00

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Buy the flip flops $270.00

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Buy the sunglasses $290.00

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


man in new york wearing a cool outfit
man in new york wearing a cool outfit

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


man in cool striped suit in new york
man in cool striped suit in new york

BUY THE SUIT $Prices vary

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BUY THE SHIRT $125.00

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BUY THE LOAFERS $298.00

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


man wearing a sweater vest holding a skateboard in new york
man wearing a sweater vest holding a skateboard in new york

Buy the shorts $22.00

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


man sitting in new york
man sitting in new york

Buy the sunglasses $367.00

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Buy the pants $11.99

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Buy the boots $219.00

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


person in new york wearing a cool outfit
person in new york wearing a cool outfit

Buy the sandals $110.00

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


man in new york with a cool bag and shirt
man in new york with a cool bag and shirt

Buy the shirt $Prices vary

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


man in new york with a tote bag
man in new york with a tote bag

Buy the vans $65.00

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Buy the tote $44.95

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Buy the jacket $Prices vary

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


man in a handsome blazer in new york
man in a handsome blazer in new york

Buy the blazer $1,195.00

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Buy the loafers $629.00

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


man wearing cool outfit in new york
man wearing cool outfit in new york

Buy the jeans $328.00

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Buy the shirt $325.00

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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.


man and woman wearing cool clothes in new york
man and woman wearing cool clothes in new york

Buy the jeans $Prices vary

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Buy the tote $35.00

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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.


man in new york holding a book
man in new york holding a book

Buy the shirt $Prices vary

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Buy the shoes $495.00

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


man dressed in business casual in new york
man dressed in business casual in new york

Buy the belt $195.00

Buy Now

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


man wearing a cool blazer holding a coffee in new york
man wearing a cool blazer holding a coffee in new york

Buy the sunglasses $163.00

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Buy the loafers $585.00

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Buy the blazer $Prices vary

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


man in new york wearing shorts
man in new york wearing shorts

Buy the shorts $Prices vary

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Buy the boots $229.95

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


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the tee $37.99

Buy Now

Buy the jeans $44.00

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Buy the boots $595.00

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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.


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the crewneck $125.00

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Buy the jeans $59.99

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


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the jacket $499.00

Buy Now

Buy the shoes $540.00

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Buy the sunglasses $995.00

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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.


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the suit $4,250.00

Buy Now

Buy the shoes $852.00

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


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the sweater $390.00

Buy Now

Buy the pants $225.00

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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.


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the shirt $69.95

Buy Now

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


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the jacket $118.00

Buy Now

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


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the loafers $920.00

Buy Now

Buy the sunglasses $682.00

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


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the jacket $440.00

Buy Now

Buy the pants $390.00

Buy Now

Buy the shoes $Prices vary

Buy Now

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.


man in cool blazer in new york
man in cool blazer in new york

Buy the blazer $Prices vary

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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.


person in burgundy pants in new york
person in burgundy pants in new york

Buy the pants

Price: $170.00

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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.


man in a plaid jacket and blue jeans in new york city
man in a plaid jacket and blue jeans in new york city

Buy the shoes

Price: $625.00

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Buy the jeans

Price: $147.33

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Buy the jacket

Price: $1,350.00

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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.


man in funny hat, green tee and purple zip up in new york
man in funny hat, green tee and purple zip up in new york

Buy the shirt

Price: $98.50 $73.88

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Buy the jacket

Price: $297.00

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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.


man in striped shirt and baggy pants in new york
man in striped shirt and baggy pants in new york

Buy the pants

Price: $165.00

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Buy the glasses

Price: $175.00

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


man in white shirt and jeans in new york
man in white shirt and jeans in new york

Buy the shirt

Price: $864.00 $742.00

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Buy the tote

Price: $625.00

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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.


guy in new york city wearing shorts and a t-shirt
guy in new york city wearing shorts and a t-shirt

Buy the shorts

Price: $315.00

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Buy the sneakers

Price: $790.00

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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.


man wearing cool outfit inside of a store in new york
man wearing cool outfit inside of a store in new york

Buy the shirt

Price: $132.00

Buy Now

Buy the boots

Price: $280.00 $123.00

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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.


two men wearing cool clothes on the streets of new york
two men wearing cool clothes on the streets of new york

Buy the jacket

Price: $Prices Vary

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Buy the pants

Price: $375.00 $244.00

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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.


man wearing a ralph lauren polo on the street of new york
man wearing a ralph lauren polo on the street of new york

Buy the vest

Price: $248.00 $174.99

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Buy the sneakers

Price: $105.00

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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.


person in new york wearing cool glasses, a white hat and a yellow/black shirt
person in new york wearing cool glasses, a white hat and a yellow/black shirt

Buy the glasses

Price: $485.00 $301.00

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Buy the jacket

Price: $275.00

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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.


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

BUY THE COAT

Price: $132.00

Buy Now

BUY THE TOTE

Price: $250.00

Buy Now

BUY THE SNEAKERS

Price: $90.00

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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.


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the vest

Price: $100.00

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Buy the clogs

Price: $150.00

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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.


man in hat in new york
man in hat in new york

Buy the jacket

Price: $395.00

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Buy the cardigan

Price: $259.00

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Buy the shoes

Price: $450.00

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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.”


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

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.


man in red shirt in new york
man in red shirt in new york

Buy the trousers

Price: $49.90

Buy Now

Buy the SNEAKERS

Price: $240.00

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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.


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy the loafers

Price: $195.00

Buy Now

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.


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy THE T-SHIRT

Price: $20.00

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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.


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy THE SUNGLASSES

Price: $119.69

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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.


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy THE SHIRT

Price: $98.00

Buy Now

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.


Street Style Looks in New York, as Spotted by SPY Agents
Street Style Looks in New York, as Spotted by SPY Agents

Buy THE SHORTS

Price: $395.00

Buy Now

Buy THE SHOES

Price: $695.00

Buy Now

Buy THE SUNGLASSES

Price: $550.00 - $1,895.00

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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.


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