What to Wear on a Date: Dress for Success With These 5 Pieces

By Elliot Aronow

Dressing for a date can be a little tricky. A lot of dudes tend to treat a date like a sexual job interview and really overdo it when it comes to power dressing. And while there’s nothing wrong with wearing a rakish double-breasted suit, a spread-collar shirt or immaculately polished benchmade shoes to work, those Gordon Gecko-inspired pieces are better suited to land you props in the boardroom, not a ticket to the bedroom.

In simpler terms: Dress nice, but not too nice. Be casual, but not too casual. Like always, it’s all about hand-picking the best elevated basics (button-down shirts, minimal sneakers, grey trousers) and styling them up or down according to your individual taste. We are just offering up some awesome ingredients here. The rest? That’s just you cooking.

And while we have your ear, here are three really quick etiquette tips to help make your date a big success. Remember, not even the dopest outfit can compensate for shitty manners. Put away your phone. Ask your date lots of questions about their (creative, not sexual) passions and their professional ambitions. Don’t talk shit about any of your exes. That’s it. Go get ‘em, tiger!

Every dude needs some dope leather in his rotation. For date night, we highly recommend going with a classic suede trucker jacket. It’s less of a look than a butch motorcycle jacket, but still conveys a lot of masculine energy. For an upmarket piece like this, you want to invest in the best, as good leather can outlast anything (hopefully not your marriage). Look for a slim-fitting model from a heritage brand like Schott. It’s been meticulously hand-crafting gourmet leather pieces since the days when picking up your date in a horse-drawn carriage was de rigueur.

If there’s one thing that is an instant turn-off on a date, it’s seeing a dude in his “going out” shirt. You know the kind: slick, a little shiny, maybe with a contrasting design on the inside of the collar. Terrible! Instead, take a cue from classic men like JFK and Steve McQueen and rock an “Ivy League Style” button-down collar shirt, like the one pictured here. It’s a little retro and just the right kind of laid-back. As a bonus, the longer collar points will draw your date’s attention upward and elegantly frame your handsome face.

A lot of guys would think to wear some smart black dress shoes on their date, while others might feel more comfortable going with a more laid-back low-top sneaker. Our advice: Split the difference and roll up to the spot rocking some elegant leather slip-ons. The minimalist design and luxe materials will prove you are no slouch, but the inherently casual vibes of a slip-on add a breezy note to your outfit. These black Vans with porcini accents would be perfect.

Each element of a great date night outfit should be a reflection of one of your best qualities. To demonstrate that you are dependable, unmoved by foolish trends and of solid mind, we highly recommend sporting a pair of classic grey trousers. Not only do they play nice with everything from dapper blazers to swaggy leather jackets, you can also wear them straight from work without looking like you’re making a sales presentation. To finish the look, pair yours with some bold socks and an understated shoe.

This one is obvious—you want to smell good on a date. There are few rules for wearing cologne on your big night. The first: Don’t try out a new scent for the first time. The second: A cool dude is seen before he is smelled. Wear enough to make that first hug a beautiful experience for the both of you, but not so much that your artificial pheromones compete with your delicious steak au poivre. To apply, simply spray a few pumps into the air in front of you and walk into the cologne. For a manly cologne we can’t get enough of, try one of NYC perfumer Odin’s signature scents.