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Four First Dates, Four Outfits

Your first date will be over before it starts if you don’t dress to impress. Here’s how to style yourself for each level of formality.


It’s all well and good to mythologize first dates and believe that when you find your soulmate you’ll look deeply into each others’ eyes while everything else blurs in the background. like smooth bokeh at f/1.8. Most of the time that’s not what happens, though: You’re asking questions, sniffing around for pheromones, looking at the way she’s dressed. She’s doing the same, and while you may not win her heart by dressing well, you can certainly lose out on a second date by dressing like a schlub. Dress well and dress for the occasion — and your winning personality will take care of the rest. Here are some suggestions for how to elevate your style on that all-important first date.

Taking Out Honey Ryder


Start practicing your martini order — shaken, not stirred — because you’ll need to act suave as hell to pull off this formal attire. Done properly though, knowing you have to wear a tux can relieve some of the pressure of what to wear. Just make sure your date knows ahead of time that you’ll be dressed to the nines.

Brooklyn Tailors Tuxedo Jacket ($770)
Brooklyn Tailors Tuxedo Trouser ($305)
J.Crew Ludlow Piqué Tuxedo Shirt ($98)
Kingsman Bow Tie ($125)
Brooks Brothers Silk Formal Hose ($40)
Alice Made This James Rhodium Cufflinks ($248)
Dior Eau Sauvage ($65)
Detroit Watch Company M1-Woodward Silver Dial ($1,850)
Magnanni Cesar Black ($350)
David Kind Richmond Glasses($295)

Casual (But Not Too Casual)


Dating in the 21st century is rarely strictly formal, but you can still show a flash of class with your dress. Don’t wear dad’s old blue collar or your high school dance corduroys. Invest to impress with some of these quality casual threads.

Rag & Bone Graydon Pant Beige ($140)
Onassis Dobby Dot Shirt ($168)
Steven Alan Bucket Pocket Oliver Jacket ($346)
John Lobb Buckles William II ($1,480)
Oak & Oscar The Burnham Watch ($1,650)
Quixotic The Monday Pocket Square ($35)
Falke Henna Sock ($30)
Kiehl’s Essence Oils ($26)

Flatteringly Relaxed


You might have a special place in your heart for the bong water stained Phish ’97 European Tour T-shirt, but your date definitely doesn’t. Casual doesn’t mean pajamas. Take advantage of the casual setting to show off your laid back side, but keep it classy with a style that’s still noteworthy.

Mister French Long-Sleeve Linen Shirt Aegean Sea Blue ($148)
Cuise De Grenouille Gunter Chino Slim-Fit ($55)
Hickoree’s The Hill-Side Sneaker ($184)
Liberty United Gunmetal Cuff ($345)
Made Eyewear Hudson Tortoise ($124)
Braun Men’s Classic Analog Watch ($200)
Agua de Colonia Concentrated Cologne ($25)

Dating on the Summit


Congratulations, you’ve thought outside the box and decided that a hike would make a great first date. You’re right, but your date doesn’t want to see your hairy chest and cargo shorts when she’s getting to know you. Be the outdoorsman she’s seen in the magazines by dawning the perfect adventure gear.

Topo Designs Camp Shorts ($89)
Western Rise Pioneer Pop-Over ($85)
Farm to Feet Cokeville ($20)
Osprey Stratos 24 ($120)
Klean Kanteen Stainless Steel Tumblr ($10)
Suunto Ambit3 Peak GPS Watch ($352)
Scarpa Men’s Oxygen GTX Hiking Shoe ($189)
Parks Project Trail Arrow Camp Hat ($34)
Burt’s Bees Herbal Insect Repellent ($7)

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