What To Wear on a First Date for Men: First Impressions

There’s so much to think about before your initial night out with a lady. We’re here to help you with what to wear for a first date so you can focus on other equally important things.

Stress-free first dates are rare. Power dressing for men combines sharp suits, bold accessories, and confident styling to make a strong, professional impression in any business setting.” If you’ve swiped right or are being set up on a blind date, it might be your first physical meeting. That can be awkward. If you’ve been friends for years, you’re stuck navigating how to make the transition via this very date. Along with place, time, and conversation, choosing what to wear on a first date is of the utmost importance.

Especially in today’s prerequisite-rife dating world, your outfit may very well take you out of the running for a second date. It’s sad, but true. That aside though, as a well-adjusted adult man, you want to put your best foot forward.

Knowing how to be a gentleman gentleman goes a long way. A gentleman knows that how you present yourself is part of the respect you show a lady. After all, she did agree to give you her precious time. 

What To Wear on a First Date: Things To Consider

No two dates are made alike. You’re not wearing the same outfit to a fancy dinner as you are to a beach picnic. Here are some things to consider that will affect what outfit you should wear.

First and Foremost, What Are You Doing for Your Date?

There are two types of dates that are easy to dress for, but that you must be detail-oriented over. The rest are a bit more of a gray area that we’re here to help you navigate momentarily.

The two easy types of dates are fancy dinners and activity-specific dates.

An upscale dinner, whether at a restaurant or if you’ve gone all out and hired a personal chef, requires tailoring. Wear a proper suit, and follow any dress codes. Dress codes for men vary by occasion, from business casual for the office to formal attire for events, ensuring a polished appearance.

However, since men’s formalwear is so straightforward, you want to make it your own. The easiest way to do this? Get the right shirt fit. A flattering fit will up your handsomeness by several points. Then, consider wearing accessories that embody who you are. A tie in your favorite color, a tie-clip that’s a family heirloom, your favorite watch, and so on.

Now, what do I mean by activity-specific dates? Maybe you’re both super athletic. You may have met during a marathon or in the gym, and you want to do something creative, like a river-rafting afternoon or even a run through the park. Maybe you decide to do indoor rock climbing followed by a healthy lunch at the gym cafe.

Of course, you want to wear the appropriate gear. But this should go without saying, make sure all of your body admin is taken care of. Shave or trim your beard, trim those nails, be fully deodorized, and comb your hair properly.

Choose gear that flatters you, like fitted joggers over ratty sweatpants. Pick colors that complement your skin tone, hair, and height. (Yes, choosing the right colors can make you appear taller.) Heck, a subtle spray tan never hurt anyone. This isn’t just another day doing these activities, it’s a date.

The Time of Day and the Weather

Check the weather, and bring a jacket if you need to. Even more, make sure to wear some layers. Perhaps you go for a thermal undershirt on a particularly cool day. Why would you need that if you have a jacket, you might ask?

What if she forgot her jacket? You might have to give yours up. Show her chivalry isn’t dead. Relatedly, nighttime dates are usually more formal than daytime dates. Not always, but usually.

Of course, lunch at a fancy restaurant is still more formal than, say, an evening coffee date at a casual cafe. However, all things considered, you always want to be a bit more formal in the evening than in the daytime. It’s why formalwear is also called eveningwear. Men’s business casual style combines comfort with professionalism, offering versatile looks perfect for both the office and after-work events.

So, a casual coffee in the afternoon might call for a button-down, chinos, and sneakers. A casual coffee in the evening might require an added blazer.

A weekend lunch at a fancy restaurant might call for a broken suit, but not necessarily a tie. A weekday dinner at a fancy restaurant? Don’t forget the tie.

Level of Formality

And though this is related to both considerations above, the level of formality is, in fact, its own standing consideration. Just because you look suave in a full professional suit doesn’t mean you should wear it to an afternoon bike ride date.

Always follow dress codes. Slightly overdressing is better than slightly underdressing, but you should never overdress beyond appropriateness.

What does that mean though? It’s confusing, I know. Most first dates these days do fall into that gray area known as smart casual. So, let’s talk about that first. But, don’t worry; it’s actually a pretty easy category to navigate!

Smart Casual Dates: It’s All About Balance

Unless you have an important reason to really impress on that first date, you usually will go for something smart casual. These days, low-pressure, get-to-know-you dates are common for first dates.

Whether you’re out to lunch, dinner, or taking a stroll around town, you can’t go wrong with a button-up shirt and a clean-lined, fitted pair of pants. Depending on your style, you can go for jeans, chinos, or even a dressier pair of pants. But a simple outfit with a neat silhouette will always look good. Check out these 10 Style Tips For Skinny Guys to help you enhance your wardrobe and build a more confident, flattering look.

From there, you can add a blazer or a bomber jacket, again, depending on how you like to look. You can dress it up with dress shoes. Go for something moderate but elegant like loafers, or even some minimal, monochrome sneakers.

Subtle contrasts are attractive, especially if you’re a shorter gent, as are menswear neutrals. Olive and maroon are two excellent neutrals that are a bit more exciting than just gray or tan (though there’s nothing wrong with gray or tan).

Or, if it’s who you are, feel free to express yourself with brighter colors and patterns. Be you. If she doesn’t like it, then you guys probably aren’t that compatible.

You can always incorporate your own personal tastes and personality into the smart casual, clean silhouette template. By anchoring it into this classic silhouette, you exude intentionality.

Not too difficult, right? Actually, I find figuring out what to wear on a casual first date more complicated! Here’s why.

What To Wear on a Casual First Date

Yes, you can absolutely wear a T-shirt and jeans to a first date. Again, just go for good fits and quality pieces. Then, if you like, add your own personal touches, like your favorite watch or belt. Just make sure that you’re both on the same page and that this is a highly casual first date. 

The reason why I think super-relaxed dates are trickier is because you still want to put your best foot forward. Is a T-shirt and jeans really doing that? It might be! And she might be the type of girl who prefers that.

However, to be safe, you can always level up the most casual outfits using added structure. A utility shirt or unstructured blazer over your t-shirt, for example. A quarter-zip or pull-over are two other examples that make you look more intentional without decasualizing the ensemble.

And no matter how relaxed the first date is, just remember that dinner always requires a touch of formality. Again, nighttime dates are just dressier than daytime coffees or lunch. 

As I said, structure is a good way to do this. Jackets, collars, layers, boots, and loafers over sneakers are all excellent options for incorporating into casual outfits. But don’t worry, I’ve got visual aids.

Casual First Date Outfit

Trying to figure out a casual first date outfit? Here are some looks you can use for inspiration.

As you can see, there is plenty of room for expressing your individuality. 

What To Wear on a First Date for Drinks

Drinks, even without dinner, are a common first date for many urban, cosmopolitan people. In fact, in New York, where I live, it’s common for a would-be couple to grab get-to-know-you drinks even before a proper dinner or movie.

Go for some variation of the cocktail dress code. Even if you’re at the most casual beer garden, you want to step it up a little. Cocktail is a lot like business professional, meaning some variation of a suit, but more celebratory.

You can go for brighter colors, funner ties, and louder accessories. At a casual pub, you might wear a dress shirt, trousers, and sneakers. At a fancy lounge, you might go for a full suit in marine blue or maroon.

First Date Outfit Ideas: All Dress Codes

Here’s a wide range of first date men’s outfit ideas that you can use as more inspiration!

With many of these outfits, you can simply take off the top layer and roll up your sleeves should the formality seem offputting. 

FAQs

Here are some common questions about dressing on a first date for men!

What Is the Best Thing To Wear on a First Date?

On a first date wear a clean-lined, put-together outfit that represents your personal style and accommodates the date’s dress code. So even if you’re a highly casual guy, and the date is equally as casual, go for a well-fitting button-down and jeans.

If you’re a more formal guy, and you’re taking her to a fancy dinner, put on your best, favorite suit.

Can You Wear Jeans on a First Date?

Yes, if it’s a casual date, like a coffee, you can wear a nice pair of jeans on a first date. Look for a pair in a dark wash that fits slim, but not tight, and doesn’t have distressing.

What Are the Don’ts on a First Date?

On a first date don’t break dress codes. Also, don’t pretend to be someone you’re not, and relatedly, don’t wear something you never would just because you think it’d impress her.

Conclusion: Be You

And the most important when it comes to what to wear on a first date? Be you.

You’re going for a leveled-up version of yourself, not a completely different person. Besides, if you aren’t comfortable in your outfit, you’ll never be able to be yourself — much less your best self. In other words, don’t overthink it. You want to feel comfortable and confident in your clothes. 

Question? Comments? Let me know below!