Men's Fashion Date Night Tips

It’s taken a lot of gumption to get to this point. Whether you’re risking a blind date or taking the online dating route, it’s not always easy to put yourself out there. And if your next “date night” comes with a long-term relationship, it can feel like a big production. So, what should you do to look your best? How can you avoid like feeling overdressed—or worse, underdressed? Here are some things you should keep in mind for men’s fashion on a date night.

Rules of Thumb for Date Night

Before we start, there are some basic lessons you’ll want to absorb about date night men’s fashion:

  • Show you tried. Even if you’re taking out a long-term partner, you should still dress up like you’re trying to impress. Don’t lower the expectations because you know this person well already. Keep up the “dating” mentality by continuing to put your best foot forward.
  • It’s better to overdress than to underdress. If you underdress, you can run the risk of not living up to a restaurant’s dress code, or just plain feeling embarrassed. You can avoid both if you take care to be one of the sharpest-dressed men in the room.
  • Keep it simple. It can be tempting to overcomplicate date night and turn it into a veritable fashion show. But you’ll do just fine by sticking to some fundamental men’s fashion staples.

What Men Should Wear for Date Night

With the rules of thumb out of the way, let’s talk specifics. What should you wear for date night? You might find that there’s some variability depending on what you have planned, but you can’t go wrong with some of the following items from the Vintage 1946 collection:

Quarter Zip

A simple monochromatic outer layer with some basic textural contrast that can highlight a crisp pair of jeans or khakis. Put it together, and you’ll have a light, casual outfit for a wide range of different date types.

Space Dyed Jersey QZip in Light Grey

Stretch Canvas Shirt In Woven Navy

Button-Down Shirt

A nice mix of casual and dress-up, giving you the buttoned appearance that’s great for restaurants as well as casual events like heading out to the movies.

Twill Pants

Of course, jeans always work—but what if you want to provide a little bit of contrast to your outfit? That’s where we recommend Military Twill Pants. The cotton twill is tremendously comfortable, while the military-style fit will help cinch together an outfit with a little bit of formality, giving you that “date night” look with something as simple as putting on a great pair of pants.

Military Twill Pants

More Great Options At Vintage 1946

When you dress for date night, you’re not just dressing for yourself. You’re dressing for that person sitting across the table. Be sure to browse the full range of options here at Vintage 1946 for great date night fashion ideas.