What to Wear on a First Date: 2 Go-To Outfits for Men

What to wear on a first date right now is arguably a very pressing question since Valentine’s Day is on the horizon, after all. But there’s never a bad time to reexamine what you’re wearing on a date. Heck, even landing a face-to-face date means you cut through the digital noise out there, so you might as well dress stylishly for the occasion. Make no mistake though, a date night can take on a life of its own, especially if you subscribe to the idea that one date can really become … two (dinner at one spot, drinks at another). So, we’re offering up two ideas when it comes to what to wear on a first date: Casual and dressy, each with its own merits. Good luck out there.

The Casual Ensemble

TravisMathew Matchmaker Jacket – $175
TravisMathew Matchmaker Jacket

You’re getting soft flannel fabric, plus the casual and rugged appeal of both a shirt and a jacket in this winter-ready piece. A more unique option than a standard winter puffer jacket, and one that you easily drape over your date’s shoulders if need be (people still do that, right?). This is a fail-safe top layer when it comes to what to wear on a first date.

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Taylor Stitch California Shirt in Everyday Chambray – $118
Taylor Stitch California Shirt in Everyday Chambray

As reliably solid and timeless as can be, this crisp chambray shirt is a stone-cold classic from Taylor Stitch. No matter where you go or what you do, we think this stylish chambray shirt is going to impress your date, no questions asked.

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Proof Rover Pants – $98
Proof Rover Pants

The Proof Rover Pants pull out all the stops when it comes to versatile (yet casual) date night style. With the look and feel of denim or classic canvas work pants, these are polished yet laid back. That sounds to us like the perfect pair of pants to wear on a first date.

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Beckett Simonon Morgen Sneakers – $149
Beckett Simonon Morgen Sneakers

While you could reach for a pair of classic leather or suede chukka boots, we think vintage-inspired sneakers are a neat change of pace, especially if you live in a more temperate climate. Think classy and sharp, without overdoing it.

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V76 by Vaughn Styling Cream – $20
V76 by Vaughn Styling Cream

Reach for a styling cream that nourishes and gives some structure to your ‘do. And leave the ball cap at home, even on a casual date night.

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Filson Mackinaw Field Watch – $400
Filson Mackinaw Field Watch

There’s a solid chance Filson makes the bag you carry every single day — turn to this heritage brand for a reliable, rugged field watch that stands out quite nicely on, say, a more laidback brewpub outing.

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Duke Cannon Solid Cologne – $25
Duke Cannon Solid Cologne

A new addition to your grooming routine, Duke Cannon’s Solid Cologne is an everyday essential that’s going to pleasantly upgrade your entire casual ensemble. The Land scent is at once subtle and classic. It’s exactly the right aura to project on a night out.

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The Dressy Ensemble

Indochino Hemsworth Navy Suit – $369
Indochino Hemsworth Navy Suit

Does dressing up these days always have to mean reaching for a suit? Not necessarily, depending on where you’re going. But if you need to suit up, you might as well put on a well-fitted, classically designed navy suit that’s a heck of a steal in terms of price.

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Institchu Bedarra White Shirt – $89
Institchu Bedarra White Shirt

If you’re saving money on your suit, you should splurge on your shirt. After all, the right white dress shirt can work day after day, week after week, in situations where you don’t even need a suit. And the crisp, classic Bedarra White Shirt from Institchu exudes refinement and taste, plus versatility.

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The Tie Bar Burgundy Wool Knit Tie – $25
The Tie Bar Burgundy Wool Knit Tie

Nod toward winter with a rich burgundy knit tie in a seasonally ready fabric like wool. While most knit ties feature a square, this tipped tie is just a little more dashing.

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Jack Mason Aviator Watch – $495
what to wear on a first date men jack mason aviator watch2

Versatility is also key when it comes to your watch. The Jack Mason Aviator Watch, in both its black dial and white dial iterations, is equal parts rugged and refined. As they say, a watch is arguably one of the things to catch your date’s eye, so make yours a great one.

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Pantherella Cashmere Socks – $72
Pantherella Cashmere Socks

These socks are loved by menswear aficionados and global jet setters alike for their durability, style, and comfort. They’ll prove just as effective on your date night.

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Rhodes Dean Boots – $220
Rhodes Dean Boots

Shoes are every bit as critical as the rest of your outfit, especially when navigating slippery winter streets. The Rhodes Dean Boots deliver excellent traction, plus sleek, date-ready style.

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If you’re a planner and are just looking at this article to prep for a potential first date, but haven’t actually gotten one yet, here are a few useful tips on how to ask a lady out.

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