The Measure

Exploring what it means to be a better man.

First Rate Dressing Tips for a First Date

October 7th, 2015

You’re meeting in 20 minutes and you’re standing in front of your closet… almost naked. Well, that look won’t work. You’ve got the conversation skills, the manners (Thanks, Mom!), but what to wear? Don’t worry, let me help.

But before I tell you which shirt to pick, let me remind you of two important things.

  1. People will notice what’s on the inside more than the outside. So be comfortable being you, and you’ll look that much better.
  2. She’s probably concerned about whether what she’s wearing looks good, too. So calm down, it’s not just you. Worrying is a natural part of the process.

So the first step: Don’t freak out.

Second step: Know what to avoid and what to aim for. Here are a few pointers that won’t steer you wrong.

Leave T-Shirts at Home

Unless you’re going on a day hike or a beach date, leave the T-shirts at home. You can still be rugged, but let’s shoot for ruggedly refined, okay? Word to the wise: You’ll never go wrong with jeans, chinos, and a classic flannel.

Check out: The Humboldt shirt in Red.

Nobody Looks Bad in Blue

If you’re afraid your beard and a flannel will make you look too much like a lumberjack and not the “rustic stud” look you were going for, throw on a blue shirt. Because nobody looks bad in blue. Add khakis and a brown belt, and you’re out the door.

Check out: The Auckland shirt.

A Gentleman Always Has a Jacket

Is it cold out? Doesn’t matter. A sweater or jacket over your arm is not just an accessory but quickly becomes a shawl for her, if needed. You gentleman, you.

Check out: The Hudson Sweater in Dark Navy

Handle the Bill With Class

If your wallet looks like it’s spent too much time in the sun (or has Velcro) it’s time to put it out of its misery. You need something that’s subtle but stylish, a wallet carries everything you need and nothing more.

Check out: The Bi-Fold Wallet in Green.

Don’t Blow It Because of Your Belt Buckle

Nothing’s worse than being “that guy with the weird belt.” You know who we’re talking about. Keep your pants up (at least for now) with a classy, understated belt. And stay away from the giant Harley-Davidson buckle.

Check out: The Post belt in Brown. Simple and clean, this belt fits perfectly with jeans.

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