What to Wear on a First Date for Men: The Ultimate Guide


Finally getting the chance to take your crush out on a date? Let’s not mess up the day before you even get out of the house. Thinking about what to wear on a first date can be extremely intimidating and nerve-wracking. What if you try too hard? What if you blow it up by underdressing? 

We completely understand how you feel! In this article, we’ll be going over some basic things to take into consideration before stepping out of your front door. Furthermore, we’ll also include a couple of pro tips at the end which will easily swoon your lady. 

Think About The Date

Before you start taking out the trenchcoat or rocking that new denim jacket you just bought, think about the date. Where is it going to be and what’s the temperature of the day? If you’re on your way to a romantic dinner, dress up a little extra with some leather shoes and a long-sleeved polo. 

Otherwise, some board shorts and a clean polo shirt would be great for outdoor activities. Your outfit will very much depend on the setting of your date and the activities you’ll be doing.

The First Impression

Your first impression is gonna set you up for all impressions henceforth. If you pull up wearing a pair of joggers, your lady isn’t gonna expect you to wear a suit on the second date (good luck getting another one if you’re wearing sweats).

We don’t want you coming up to your date looking like the best you’ve ever been, but you should definitely try to be groomed. Have you met before? For complete strangers, dressing up in simple or toned-down versions of your aesthetic is the best way to let them feel your vibe. You can gradually introduce and be more outgoing with your fashion in progressing dates. 

However, if this is a long-time-friend turned crush, think about how you want to make her feel. A great way to impress someone like this is by putting on something that she doesn’t often see. So if you’ve always been hanging out in shirts and jeans, spice it up a bit and put on a jacket and some sneakers. Adding layers to your style is a great way to add depth to your outfit.

Does She Know Your Style?

If she’s already familiar with your style, try mixing things up a bit in small little details. Now’s the perfect occasion to put on that good-looking outfit you’ve been meaning to wear the last couple of weeks.

Perhaps you don’t really have a style yet, but she knows what you usually wear. Well, dates are a great way to build a great foundation for your aesthetic. Though this might be a bit costly, if you can afford to do so, we suggest buying some new clothes.

A couple of dollars for a plain white shirt and some fitted jeans can go a long way. Though this might feel like a boring outfit, it is actually the best form of smart casual there is. The white shirt is simple yet clean. Jeans that fit well show an attention to detail that loose legwear just wouldn’t convey. 

Don’t forget the shoes! You don’t need the latest Nike or Yeezy shoes, but a clean pair of shoes will definitely elevate your look. As most people like to say, shoes make up 80 percent of your outfit. 

Be Comfortable

It’s completely normal to feel like a nerve-wracking mess before a date. This is especially common for individuals who may not start with the best self-esteem or confidence. However, screw layering yourself in clothes, having a sweatless and smooth date should be your top priority.

No one wants to be with someone who’s sweating a lot, nor be the person who’s actually sweating. Even if it isn’t a hot day, an extra-tight shirt can make you fidget by your pits or feel constrained. This can easily make you feel more nervous than you already are, and we all know how it feels to get into that spiral staircase of being self-conscious.

Believe us, your girl will notice you every time you reach for your pants to unstick your groin. Wear something comfortable, but don’t underdress. We’ll explain the specifics of what you can wear and what you should avoid in the segments below.

What To Wear

Now here’s where the magic happens, or until tonight anyway (If that’s both your thing). What should you actually wear? Well, there’s a lot that we’ll cover in this list, as well as specific things you should generally take note of. 

At the end of the day, wear something that compliments your personality. Just because this date goes well doesn’t mean you can wear the usual flip flops to the next one. Understand that you’re going on a date to let that someone come into your life. To see how you are as a person. Don’t try to sell a facade or wear something that isn’t your style.

We understand the feeling of wanting to impress on that first date, but at the end of the day, what’s important is that she gets to know who you are. What you like and how you like to dress. Now don’t take this as an excuse to not be groomed! This is simply a reminder to not feel obligated to wear what’s “cool” on social media just so you can seem hip. 

Posture, Wax, Cologne, & All The Details

Skincare is something everyone needs to do. There’s nothing worse than feeling like your face is full of oil and grime three hours into your date. Put on some sunscreen or moisturizer, even if you have to borrow it from your sister.

The next best thing you can wear is proper posture. For you gamers, try to get rid of the gamer neck if you can. A quick ten-minute video on YouTube for neck and back stretches can go a long way to help you stand straight. 

And before you leave, don’t forget to put on a spray of cologne on both sides of your pecs. For added gentleman effect, spray the scent on your wrist and rub your wrists together. Dab each wrist on both sides of your neck, in case the lady gets too close. 

Lastly, shave Mr. Sergeant Junior. You never know what the night has in store for you. Additionally, greeting your date with the Whomping Willow is the last thing you want.

With that in mind, let’s put on some clothes!

Keep Things Simple

You don’t need to wear a lot of layers to your date so you can feel a bit more sophisticated. While it’s true that layers add a level of detail to your outfit that women do notice, keeping things simple is a really great mood setter for casual and cute conversations later on.

This especially helps if your date is also nervous about meeting you. Put on a plain shirt, a snug pair of jeans, and some matching clean kicks to set that friendly mood. Don’t worry, since you’ll feel calm too, your conversations should flow easily in that setting.

The secret to making a simple outfit work is in the fit. Make sure your pants and shirt hugs your body instead of sagging. Pick a clean and ironed out pair of clothes as well, and always try to clean your shoes beforehand.

Absolutely Avoid Joggers Or Sweats

Remember that part about being underdressed? Joggers. Sweats are an incredibly big no-no for first dates. You may as well come up to the date in boxers with a toothbrush in your mouth. It might be acceptable to hang out with your friends in sweats, but for a lady, that’s a huge buzzkill. 

There’s nothing classy about joggers, even if they are expensive. If you’re bringing her out to a playground like American Ninja Warrior, then we might give you a pass for wearing sweats. Other than that, try to avoid it.

Put On Some Layers

Having overlays on your body is a great fashion tip that anyone can use. Wearing a grungy ACDC shirt? Cover that over with a blue denim jacket, but leave the buttons open. Layering your clothes adds a lot of depth to your outfit.

If it’s especially cold outside, grab yourself a thick brown trenchcoat and pair it with a white turtleneck underneath. Now slide into a slim fit pair of black jeans and put on some Chelsea boots. Having a thick turtleneck underneath the trenchcoat acts as a second-level of protection against the cold, in case you have to let your date borrow your coat. 

Now, don’t let the heat discourage you from putting on some layers. If it’s especially frying outside, having a thin red flannel is a perfect way to block your arms from the stinging heat. In the event that the heat clears up, you can always just tie it around your hips for extra style points anyway. 

The most important thing to do when thinking about layers is to find out what your date is wearing. If she’s gonna be decked out in layers, maybe you won’t have to get a thick turtleneck. But in the event that she’ll be wearing a dress or some light clothes, having that extra layer you can let her borrow is an ace you should always have up your sleeve. 

Lastly, here’s a pro tip: spray a little bit of cologne on your jacket. The right amount of cologne and she’ll snuggle into your coat while you’re watching a movie. 

Rock The Chinos

We love the chinos and, really, who doesn’t? Chinos are a great way to look semi-formal while keeping yourself comfortable and snug. Not as corporate as a pair of trousers, but not as rough as a pair of jeans. 

Chinos are smack-dab right in the middle of smart casual fashion, and for good reason. Artistic or historical dates like museum trips are a great place to wear a smart casual outfit. Furthermore, the smart-casual aesthetic suits a lot of older gentlemen or mature young adults.

Dressing up with a pair of light brown chinos and a white short-sleeved polo can go a long way with the right pair of dark brown leather shoes. This is a great way to tell your date that you’re dressing up for her while saying you’re confident enough to not overdress. 

Wear Something Offline

We all can’t help but ask our friends to take pictures of our outfits so we can post them online. And why should you help it? You look great and your friend took an amazing photo for your Instagram feed. 

But here’s the kicker. Try not to wear that on your first date. If you met your date on Tinder or some other dating app, then you should especially avoid wearing the clothes of the pictures on your dating profile. Surprising her with another outfit should be your biggest priority.

Furthermore, wearing something she’s already seen will make her think about the limitations of your wardrobe. This is especially important if you already have a lot of bomb outfits in your wardrobe that you can use instead. 

However, if your outfits are limited, then try to switch things up a little at the very least. You can easily do this by switching your shoes or jacket with something else that matches. 

Accessories & Final Touches

Finally, wear a watch. Having a watch is one of the most important things you can wear to a date. Of course, the type of watch you wear does speak for your personality, but if you can help it, try a metal or leather stripped watch.

If you have both, then wear one that matches the date you’re about to have. Leather watches feel classier, and can be worn for dinner dates or outdoor activities. Metal watches are, ironically, great for casual dates and can be worn to the movies or to lunch. 

Try to be careful about wearing rings, as these can feel rebellious. Furthermore, review the details of your outfit. Look around for stains, get rid of lint, and fix your hair. 

Related: Best Digital Watch for Men

Pro Tips

Now for the baby-maker. These details will change your dating life forever and can be the biggest impression you’ll leave on your date. Remember, everyone can look good but only a few people can be thoughtful to plan ahead.

Check The Weather

Getting your phone and opening up the Weather app can be the biggest thing you’ll do before a date. Are you expecting rainfall tonight? Bring an umbrella. Bring it. When your lady asks you why you brought an umbrella to your lunch date, she’ll be awestruck to think that you planned ahead in case it would rain. 

Luckily, umbrellas are uni-weather and are also great at blocking out the sun. We recommend carrying something that folds, so you won’t look like a modern-day samurai. Additionally, you can also bring something of medium size, so you’ll both have to squeeze in to protect yourselves from the rain. Romantic.

Carry Two Handkerchiefs

Yes, two. Hankies are an incredibly underrated accessory that can make a world of difference at the right time. Of course, you’ll be bringing two hankies so you won’t populate her face with your germs by handing her yours. 

Keep a handkerchief for yourself and for when you sweat, but bring an extra one for the lady. Soup stains or any kind of mess can easily be wiped with a hankie. Furthermore, she might want to take it home and clean it as a sign of gratitude. This way, you’ll both have something to look forward to on the second date. 

Bring Your Wallet

If you’re any kind of internet lurker, a few horror or sweet posts on Reddit will let you realize how common it is to forget your wallet on a first date. Personally, I’ve never done it, however, I’d probably feel my soul leave my body If I didn’t feel my wallet when the bill arrives.

Free Checklist: 10 Must-have Clothing Items for the Modern Man 🕶️

Frequently Asked Questions About Dressing for a First Date

What color should a man wear on a first date?

Any color you want, as long as you’ve understood each other’s personality. A part of the dating process is also knowing what either of you likes wearing. However, you can never go wrong with a plain white shirt, dark blue jeans, and sneakers.

What should you not wear on a first date?

Absolutely do not wear joggers. Sweats are a great way to underdress and make your date feel like you just came out of bed. You may as well be showing up with a toothbrush in your hand. Also, avoid wearing thick clothes especially for a hot day. Sweating is the wrong type of attractive liquid that you should be secreting. 

What is the best thing to wear on a first date?

Wear something simple yet personal. For example, avoid overdressing or underdressing by choosing to wear a fitting pair of jeans. Now for something personal, put on a complimentary shirt of your favorite band or movie. The first date outfit is all about not scaring your girls while showing a tiny bit of personality. 

A Final Word From The Trending Man

First dates can be nerve-wracking, but don’t let that stop you from having a good time! Remember, your first impression will set you up for all future impressions. However, at the end of the day, what’s important is that you both had fun. Relationships are sometimes nothing more than two people who enjoy hanging out with each other. 

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