What To Wear On A First Date – For Men

date night

There many times in life that you have to make a great first impression. Job interviews, meeting new people, starting out in a new school or a new city… But is there any instance more nerve-wracking than a first date? It’s easy to second-guess every decision you make, from the venue you choose to the clothes you put together. Use this guide on what to wear on a first date for men, and you’ll know exactly how to put together a great date night outfit for a nice boost of confidence.

Keeping It Casual

The first thing to remember about what to wear on a first date is that it’s not a wedding. Men don’t need to look their absolute “Sunday best” to impress. You just need to be able to put an outfit together.

That means keeping it casual. You might want to go for a little more effort than a T-shirt and jeans, but you should think in line with the classic combinations that will never steer you wrong: a two-button Henley and a pair of khakis, for example.

Here’s a date night outfit rule of thumb: you want to look good enough to sit down in a nice restaurant… but not so over-the-top that you leave your date feeling underdressed. It’s a difficult balance to strike, but we’ll help you get there with a few suggestions.

Ideal Tops and Combinations for the First Date

When deciding what to wear on a first date, the trick is to pull off a smarter version of casual than you might even be used to. If you’re a “T-shirt and jeans” kind of person, let’s add a few buttons. Here are some great pieces to get you started:

  • Oxford Washed Plaid Woven Shirt. The colors of this shirt are interesting without being over-the-top. The buttons will help show that you did more than slap on any old shirt in your closet, and this item will pair well with either jeans or chino pants. Bottom line? It checks all of the boxes.
  • Retro Cable Cardigan. For those autumn and winter dates over coffee, go for a simple-yet-textured piece like this cardigan. You can dress it up with a button-down underneath or simply wear as-is for something more casual.
  • A button-down shirt and Classic Vintage Twill pants. You have plenty of color options here, which means you can either pair these pants with one of the options above or look to your wardrobe for something that already fits. Either way, vintage twill pants serve as a great foundation for any date night outfit.

Now that you know what to look for, let’s focus on key mistakes to avoid.

Don’t Commit These Fashion Faux Pas

Hopefully the tips above gave you plenty to think about. But just in case you need some more guidance, here are the potential mistakes you need to watch out for along the way:

  • Going too flashy. It’s great to incorporate some bold colors. Red contrasting with blue, pale yellow pastels, etc. But when you put too much together, it stops being bold and starts being attention-hogging.
  • Wearing gym sneakers. They’re comfortable, they’re easy to wear, and they’re completely inappropriate for a first date.
  • Going too tight. Find an appropriate, casual fit. Even if you’ve been working out hard in the gym, too tight won’t give you that fashionable look you’re after.

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Want more ideas for what to wear on a first date for? Browse our entire collection of vintage clothing, and you’re sure to find something that will impress!