Building The Perfect Casual Date Outfit For Men

The first date is no easy task. You’re nervous about every little thing. Where should you go? Should you show up early? How early is too early? What will you do after that? And the eternal question: what do you wear?

Fortunately, there’s a great way to ease those first-date jitters: know exactly what to wear. If that seems like a tall order in and of itself, we’ve got some recommendations for building the perfect casual date outfit for men, straight from the expertly curated stock here at Vintage 1946.

For the Shirt: Keep it Smart-Yet-Casual

We’ll start with the shirt. The shirt you choose largely determines just how “casual” your look is. Getting this wrong will make you feel out of place: you don’t want to wear a T-shirt to a slightly-upscale restaurant. Similarly, you don’t want to show up in a suit and tie like you have a job interview. Where’s the middle ground? We have a couple of options here:

  • Safe option: You can’t go wrong with the versatility of Oxford Washed Gingham in Navy. This shirt is versatile enough to match stylistically with just about anything else you’ll wear. You’ll want at least a button-down shirt to ensure you look like you’re ready for a night out on the town, but unless you have big plans, anything more than this is likely too much for a first date.
  • For the bold: This Solid Oxford Shirt in Pink Lemonade is a great option for showing a bit of confidence. It has a fun bit of contrast at the cuffs to distinguish it from “office-wear,” and the color is suitable for just about any first-date situation you might come across.

Want even more options? You can’t go wrong with any of the Woven Shirts here at Vintage 1946

For the Trousers: Make it Fun

Dress khakis in the plain color are great things. They’re versatile. They’re office-ready. They’re great for job interviews, get-togethers, and just about any other time you can think of.

But this is a date, after all—you want to look like you’re ready to keep things light and fun. This is a simple principle that can serve as the foundation for the whole of a casual date outfit for men.

That’s why we recommend going a little bit outside the box when you pick the color of your vintage pants. Think about pastels. Charleston Bricks. Trousers like these Vintage Twill Sky pants that highlight other stylistic choices like the shoes you wear.

Shorts Aren’t Always Out Of The Question

Depending on the weather, of course, you can always go for a pair of Vintage 1946 shorts as well. The key is to have a little fun with it. Don’t wear the same old drab combination that you might wear to class or the office. Spruce it up a bit. Show your date that you put some thought into it—but not so much thought that you overthought it into an outfit that looks like you’re ready to do some data entry at the office.

Shop Vintage 1946

When you like your outfit, you’ll like how you look, which helps you relax and enjoy yourself while you’re on the date. After all, isn’t that kind of the point? For more great pieces to help you look and feel your best along with more casual date outfit for men options, shop Vintage 1946.