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How to Wear One Outfit, Three Ways

One set of clothes versatile enough to be worn on the weekend, at the office, or out on the town.


Here’s the bad news: there’s no shortcut to style. Choosing quality, well-tailored clothes in timeless styles (with a contemporary bent) is the only consistent way to achieve sartorial success. However, there are a few ways to milk the system, like leveraging one set of good clothes into three different outfits.

And this isn’t a “zip-off shorts/pants” set up. Gimmicks don’t work. It’s just one ensemble that is readily adapted as casual, business casual, and quasi-formal. It’s a get-up that can move seamlessly from morning errands to a lunch meeting to that reservation you finally got at Polo Bar. You’ll move through the day with ease, because everything you’re wearing is breathable, light, and easily packed away when not in use. This is upper-level outfit execution made easy, so stay confident and go get ’em, all day long.

The List of Versatile Goods
MeUndies Boxer Brief: $20
Etiquette Clothiers Abbey Stripe Sock: $24
NN. 07 Marco Slim Fit Chinos: $160
Wolverine Wesley 1000 Mile Wingtip Chukka Boot (tan): $295
Everlane Cotton Crew: $15
Maison Margiela Button-Down Oxford: $395
Everlane Singled-Sided Belt: $45
Burberry London Beige Unstructured Blazer: $995
Apolis Striped Linen Pocket Square: $30
Apolis Indigo Wool Tie: $78
Shinola The Runwell 47mm Watch: $600
Filson 24 Hour Tin Briefcase: $355

1The Casual Set Up
The pillars of this outfit are a crisp, airy white oxford from Maison Margiela and a pair of slim fit chinos from NN. 07. These two items are the base elements capable of holding your closet together for years to come. Roll the sleeves up on the Margiela button-down, wear it untucked, and cuff the chinos to show some sock. If it’s too hot, stuff the oxford in the briefcase and opt instead for the simple, perfect white tee from Everlane. The Single-Sided belt is proof that class and quality aren’t always expensive. Lastly, MeUndies boxer briefs and Etiquette Clothiers socks are A+ base layers that won’t let you down (or start you smelling).

2Class It Up a Touch
Tuck in the oxford, roll down the cuffs, and put on the Runwell watch from Shinola. The Wolverine 1000-Mile Wingtip Chukkas fit in great in the office and only get better with age. Pull out and put on the beige blazer from Burberry — it’s unstructured, lightweight, and (practically) meant to be stuffed into a bag. If the setting is more formal, add the indigo wool tie from Apolis. The briefcase has space for your laptop, too, in case you need to make the office mobile.

3Upgrade to Friday Night Formal
The goal is to walk out of the office Friday afternoon and be immediately ready for Friday night. Ditch the tie, but keep the blazer and add the striped pocket square for some panache. You can also opt to roll the sleeves up on the blazer and cuff the chinos again for a more casual evening look.

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