What to Wear on a First Date (for Men): The Do’s and Don’ts

Are you getting ready for the first date with someone new and exciting? There’s nothing quite like a first date: there’s potential, there’s pleasure, but there are also nerves.

If you’re feeling nervous about your first date, you’re not alone. A recent study revealed that 89% of people feel some degree of anxiety or tension as they get ready to embark on a first date.

How can you relieve some of that anxiety in the moments leading up to your date? Focus on putting together a great outfit.

Let’s talk about what to wear on a first date for men. When you dress well, you feel great! Keep reading for first date fashion tips.

Step One: Consider the Environment of Your First Date

The most important thing to consider when deciding what to wear on a date is the environment. Are you going out for coffee and a stroll in the park or are you going to a five-star restaurant? Naturally, the clothing you wear on those dates would differ pretty drastically. 

No matter what, you don’t want your outfit to call attention to itself in a negative way. Dressing in an appropriate fashion for the environment you’ll be in is important.

Step Two: Go for a Nice Fit

When you’re trying to dress well for a first date, cost doesn’t matter if you don’t know your true size. In other words, don’t go out and spend hundreds of dollars on an outfit that is too big or too small.

We recommend finding clothing that reveals your natural silhouette but doesn’t look skin-tight. For example, these Jasper Holland t-shirts paired with straight-leg jeans would make a perfect outfit for a casual first date.

Step Three: Don’t Overlook the Details

Are your pants wrinkled? Are you missing a button in your cuff? Does your shirt have a hole in the armpit?

While you don’t need to obsess over looking “perfect,” you do want to pay attention to these details. If necessary, grab an iron and a lint roller–and pick articles of clothing that are still intact. 

Additional Tips for What to Wear on a First Date for Men

We can’t tell you exactly what to wear. After all, we don’t know where you’re going or what your true style is. However, we can give you a few more tips that will help you pull together a great outfit that will impress your date.

Wear a Watch

If you own a watch, throw it on. A watch with a metal band is ideal for a formal setting while a sporty watch is more suited to a casual date. Watches are one of those subtle accessories that, like a belt, can make any outfit look a little more complete.

Go for Neutral Tones

Sure, a brightly patterned shirt might be a great conversation starter. Yes, there are seasons when pastels are in. That being said, you may want to stick to neutral tones for your first date.

Colors like black, grey, navy, and white are “grown up” and sophisticated. They also won’t create any distractions, allowing you and your date to focus on more important topics than your clothing.

Don’t Forget the Undergarments

You never know how a date might end. The last thing you want is to reveal your oldest, holiest, most faded pair of underwear to your date! Make sure you wear a pair that’s comfortable and that you wouldn’t be embarrassed to be seen in.

Pick Clean Shoes

Whether your date calls for dress shoes or sneakers, make sure they’re clean. A good pair of shoes can complete an outfit while a not-so-good pair can throw off the whole thing. 

If you’re wearing dress shoes, consider giving them a quick clean and polish. If you’re wearing sneakers, a little wear is fine, but don’t pick the pair you run ten miles in every day–and definitely not the pair you mow the lawn in.

Don’t Overdress

We tend to assume that overdressing is better than underdressing. While this rings true in some situations, you will really want to avoid overdressing on a first date. For example, unless the environment absolutely calls for it, you may want to skip the tie.

Why? Remember that your date may feel nervous, too. You want to help them feel relaxed in your presence, and overdressing can intimidate.

Don’t Wear Open-Toed Shoes

Yes, you can get away with wearing sneakers or loafers on a casual date. No, that does not mean that you can also wear a pair of flip-flops.

The truth is, no one is trying to look at your toes the moment they meet you. Even if you’re a once-a-week-pedicure kind of guy, it’s better to keep the toes hidden.

Skip the Hoodie, Hat, and Sunglasses

We all love a good hoodie because they’re comfortable and easy to throw on. For those same reasons, you don’t want to wear a hoodie on a first date. It’s offputting because it makes it seem like you weren’t concerned about putting effort into your appearance.

A hat and sunglasses are alright when you’re taking a stroll on a sunny afternoon, but take them off once you get indoors. When it seems like you won’t take off these particular items, it can send a signal that you’ve got something to hide.

Dress Well and Feel Great on Your First Date

If you’re looking for ways to beat the nerves on a first date, start with planning a good go-to outfit. We hope that our guide on what to wear on a first date for men has given you the men’s fashion tips you need to dress well and feel great. Want to know what to wear on other occasions throughout your life? Take a look around for more guides to fashion, accessorizing, and skin care.