What to Wear on a First Date For Men (2023 Guide)

Nervous about what you’re going to wear on a first date? This article will help men choose the perfect first date outfit.

First dates are nerve-racking. Even guys who have been on a lot of first dates can still feel anxious about them.

There’s a lot to think about. What are you going to say? Where are you going to go? And, of course, what are you going to wear?

If you have no clue what to wear, you’ll feel even more nervous, and you’ll probably end up throwing something together at the last minute.

And sure, you might be presentable, but it’ll likely be obvious that you rushed things.

Knowing what to wear on a first date is crucial to making a good first impression, and assembling a good outfit will take some planning.

So let’s get to it. Here’s our practical guide on what to wear on a first date for guys.

First Date Style – Things to Consider

Before you even think about your clothes, you need to think about your actual date situation.

There are many factors that can affect what you wear, and that’s where some planning will help.

The Location and Activities

The meeting place and activities are the most important considerations for putting together a solid date outfit.

You want to match the formality of the location (at least approximately) so that you don’t look out of place.

If you’re meeting up at a dive bar and show up wearing a blazer, you’re going to stick out like a sore thumb. Save the blazer for a formal dinner date or to wear with your best New Years Eve outfits.

But, if you arrive at a fancy restaurant in jeans and sneakers, you’ll feel equally out of place.

Remember: when in doubt, it’s always better to be slightly overdressed and than underdressed.

The Time of Day and Weather

This is another big factor. If your date is in the daytime, then you’ll probably want to lean into something smart casual style. Generally, nighttime dates call for a slightly dressier look.

This ties into location. Daytime date locations (casual restaurants, coffee shops, parks, etc.) are typically more casual than nighttime locations (fancier restaurants, clubs, etc.).

Also, nighttime is generally cooler than daytime. So, regardless of formality, you may want to bring an extra layer or jacket to a nighttime date.

On the other hand, don’t overdress for a daytime date. You’ll already have reason enough to sweat without overheating under too many layers!

What NOT to Wear on a First Date

Before we look at what to wear on a first date, let’s look at what not to wear. When it comes to first date style, avoiding mistakes is half the battle.

Here’s what not to wear on a first date:

Hoodies

Hoodies are great for casual get-togethers, but if you wear one on a first date, you’ll just come across as lazy.

Opt for less casual sweaters, such as cotton pullovers, wool crew necks, overshirts (shackets) or light jackets (bombers, Harringtons, etc.).

Sweatpants

Just like hoodies, sweatpants are way too casual and sloppy for a first date. For colder weather, try a pair of thick cotton chinos or heavier weight jeans.

If you’re going for a hike, wear performance chinos or upscale joggers instead of cotton sweatpants.

Think lululemon, not Champion.

Graphic T-shirts

As much as you might want to rep your favorite artist or TV show, that’s not a look you want to be sporting on a first date.

One possible exception here is if you’re going to a concert, but even then, consider pairing it with an unzipped jacket.

If the date goes well, you’ll have plenty of to get to know each other’s interests. You don’t have to broadcast yours on your chest 😉

Ties

Ties are a bit too formal for most dates and can make you look too corporate. Unless you’re going to a very fancy dinner or somewhere with a formal dress code, ditch the tie.

Sandals

This one’s self-explanatory…right? I hope so!

The one exception here is if you’re meeting at a pool or the beach, or if you’re going hiking and expect to navigate some water.

Even then, though, I’d go for espadrilles or loafers over sandals. If you do want to wear sandals, avoid flip flops. Go with Birkenstocks, Tevas or Chacos instead.

What to Wear on a Casual First Date (e.g., Coffee Date)

Now that we’ve gone over some basic date outfit etiquette, let’s look at some of your clothing options for casual (or daytime) dates.

Oxford Cloth Button Down (OCBD) Shirt

The trusty OCBD shirt is an excellent choice for a lot of first date scenarios. It’s classy but not pretentious, and it communicates that you put thought into your appearance. Plus, it doesn’t matter how old you are. Whether you have mastered the art of old man style or just learning how to dress for your body type, you can’t go wrong with an oxford shirt.

A flannel shirt (like the one on the right) is also a solid option if you’re in a cooler climate. I’d go with solid colors or subtle pattens vs. something loud like buffalo plaid.

If it’s going to be really hot out––or if you just live in a really warm climate––consider a linen button up instead.

Linen shirts are thinner and more breathable than OCBD shirts, but they look every bit as nice.

Polo Shirt

While many guys associate polo shirts with the preppy frat look, they’re actually quite versatile.

A polo is a good choice if it’s warm enough out for a T-shirt but you want something a bit more refined.

Polos with lots of branding can be distracting, so go for a nice minimal polo in a neutral color like navy or charcoal.

In addition, opt for a pique knit polo instead of a jersey knit. Piques are more textured and look less sporty.

T-shirt

Full disclaimer: T-shirts aren’t appropriate for every kind of date.

But a simple t-shirt that fits properly can be perfect for any first date that involves some sort of physical activity (like hiking).

If you need to layer, no problem – there are lots of great outfits you can build around t-shirts.

And if you want to stand out a little more, choose something with a subtle pattern.

Chinos

Chinos are some of the most versatile pants you can buy. They’re great for any casual situation, and you can even dress them up for business casual settings.

Chinos are nice for first dates because they go with just about any outfit. Basically, it’s hard to make chinos look bad.

Chino shorts are also an option if you need something breezier, but only wear shorts if you’re on an outdoor warm weather date.

Jeans

Jeans are a bit more casual than chinos, but they’re perfect for casual first date outfits, and they work all year around.

In general, dark wash jeans are more formal than light wash. So, if you’re going on a dinner date, go with dark wash jeans.

Either way, avoid jeans with a lot of distressing, rips and fading.

Pair your jeans with a casual button up, polo or t-shirt.

Casual First Date Outfit Ideas

Now that you know which articles of clothing are best for daytime dates, let’s look at what to wear on a casual first date.

#1: Button Up Shirt with Jeans

For more casual daytime dates, throw a casual button up shirt, and leave it untucked for a relaxed yet refined look.

If it’s a slightly crisper day, you can put a sweater on over your button up shirt for a nice layered look (and extra warmth).

This is a really flexible look that will work well for just about any kind of daytime date. Avoid jeans with a light wash and lots of distressing, though.

There’s nothing inherently wrong with lighter jeans, but they can tend to make you look like a 15-year-old who shops at H&M if they have lots of fake distressing.

Darker jeans tend to give off a more mature vibe.

#2: Polo Shirt & Jeans

This outfit is simple and straightforward: a polo, jeans and sneakers.

Again, minimalism is the key here. This polo has no visible branding, and it’s a deep navy that matches most outfits. The jeans and shoes don’t draw any unnecessary attention to themselves, either.

Learning how to wear dress sneakers with this pairing also ups your style game if casual canvas sneaker aren’t your thing.

It can also help to accessorize. For example, tossing a watch and bracelet into the mix as shown here can add some nice detail and tie your outfit together.

#3: Henley & Chinos

Another simple, understated look, this casual date outfit idea is based around a fitted blue henley and olive chinos.

The colors complement each other nicely, and the GAT sneakers add some contrast and visual interest to the otherwise basic look.

A watch and some sunglasses finish off the look.

This is a good outfit for a super casual first date, like meeting at the dog park or going for an easy hike.

#4: Casual Layers

A vest can add warmth and interest to your outfit without the bulk of a jacket. They’re great for transitional seasons.

But you want to avoid the Finance Bro look. So go with a quilted vest instead of a Patagonia fleece vest.

Also, skip the tucked in button down shirt, and opt for a casual crew neck sweater instead.

#5: Elevated Shorts

Let’s say you live somewhere hot, and you’ve planned a first date in the great outdoors.

But you’re not hiking. Maybe you’re sitting outside at a coffee shop or playing mini golf.

You don’t want to overheat, but you also don’t want to wear gym shorts and running shoes.

Go for a button up shirt and shorts, and make the outfit less preppy with sneakers instead of, say, boat shoes.

Accessorize to your heart’s content, and be ready for compliments!

#6: Tucked In Tee

Here’s an easy way to wear a super casual and comfy outfit, but still let your date know that care about your appearance: tuck in your t-shirt.

A tucked in tee is not only comfortable, but it creates a streamlined, somewhat fashion-forward look that will set you apart from the crowd.

Bonus points if you throw a light jacket on over the tee.

Oh, and this look works equally well with jeans or chinos.

#7: Polo and Chinos

If “jeans and t-shirt” had a handsome older brother, his name would be “chinos and polo”.

This is still a casual outfit, especially if you wear the polo untucked and opt for casual footwear.

Bonus points if your shoes compliment your shirt.

This outfit is perfect for everything from a walk in the park to coffee or cocktails.

What to Wear on a Nighttime First Date (e.g., Dinner Date)

Like I mentioned earlier, if you have a nighttime date planned, chances are the atmosphere will be a little fancier.

You’ll also probably need at least a little extra warmth. With that in mind, here are some garment choices for evening and nighttime dates.

Casual Jacket

If you need a bit of warmth (or just another layer), opt for a jacket.

There are many jacket types to choose from, but you could argue that the Harrington is the best all-around jacket.

The Harrington is lightweight yet structured, and it can be dressed up or down.

Most Harringtons have patterned linings that look great when you leave the jacket unzipped.

It adds a ton of depth to your outfit and gives the impression of an additional layer.

You could also go with a classic leather jacket if your date is more casual, but a Harrington is way more flexible, so it’s a safe bet.

This kind of casual jacket is perfect for a first date that involves meeting up for a couple of drinks.

Blazer or Sports Jacket

For a more formal look, consider a tailored blazer.

Blazers are often seen as more formal, but you can also dress them down by incorporating them into a smart casual outfit.

The formality of a blazer depends on its color, construction and fabric.

You can wear a blazer over an OCBD or dress shirt for a smart casual look. If it’s colder out, exchange the button up for a sweater or wear a sweater over your button up. Either way, you’ll have a snazzy layered outfit.

Sweater

Sweaters are perfect for colder weather, and you can layer them with just about anything for a dapper look.

The classic combo is, of course, a sweater over a button up, but there are tons of styling possibilities.

You can also just wear a crew neck sweater on its own, without a button up shirt underneath.

Cotton or Wool Trousers

Chinos work well for a lot of first date environments, but there are some instances where you’ll want to upgrade your pants (for example, if you’re heading to a fancy restaurant).

In these situations, a pair of wool, cotton or linen trousers will do the trick. Go for a basic/neutral color like black or grey.

Of course, if you’re not heading to a five-star restaurant, then a nice, ironed pair of chinos will probably be fine.

The important thing is to choose clothing that matches the formality of the occasion and venue.

Loafers, Bluchers or Boots

When it comes to footwear, it’s always safer to err on the side of formality.

That doesn’t mean you should rule out sneakers, but you should probably not wear those dirty Chucks you’ve had for over a decade.

How fancy do you need to go? If you have a pair of Oxfords or bluchers, those are definitely formal enough for a nighttime date.

In fact, depending on the date, they very well might be too fancy. Going down a few notches on the formality scale, you have loafers and boots.

If your style is somewhat preppy or sporty, then loafers might be a good choice for you.

Boots are a little more versatile – you can choose from a wide range to suit your needs.

Minimalist Sneakers

Finally, when it comes to sneakers, aim for minimalism. A clean pair of white sneakers or a darker pair with a sleek silhouette will look best with most outfits.

If you’re on a budget, check out our list of the best Common Projects alternatives.

Smart Casual First Date Outfit Ideas

Dressing up can be tricky, especially if you’re not used to it, so let’s look at some simple smart casual outfits for first dates.

#1: Timeless Layering

If you have a nighttime date that’s more casual than formal, you’ll want an outfit that’s refined yet not stuffy.

Pairing dark wash denim with a classic layering combo on top – button up, sweater, jacket – gives you that “put together yet laid-back” vibe that can be hard to achieve.

The jacket will provide you with a bit of warmth if you need it, and it looks great over any type of sweater and button down.

This look is great for a lot of first date situations, especially during early spring and fall.

Don’t know what to wear on a first date to dinner? Try this. Grabbing coffee? This outfit is perfect for that, too.

#2: Sport Coat and Long Sleeve Polo

For a great smart casual look, toss a sport coat on top of a long sleeve polo.

The jacket will elevate your outfit, but the polo brings it back down to earth. It’s much more casual than wearing an actual dress shirt.

Feeling fancy? Add a pocket square for a subtle splash of style. It’ll make for a nice conversation starter, and your date will appreciate your attention to detail.

#3: Tucked In Button Down Shirt

Want an easy way to dress up your denim? Tuck in your shirt.

This is such a classy, laid back look. It’s perfect for meeting your date for tapas at a wine bar.

It’s not so stuffy that they’ll feel underdressed, but it’s more elevated than what their last date wore.

To add even more nonchalance to this look, show some forearm and ankle.

#4: Turtleneck and Sportcoat

Sometimes a blazer sports jacket can feel too formal for a first date. You can dress it down by wearing a turtleneck sweater instead of a dress shirt.

This is a great date night outfit for fall and winter because it provides plenty of warmth.

You could wear an overcoat if it’s really cold out, but chances are you won’t need it.

#5: Coming Straight from Work

If you’re meeting someone after work, and you work in a business casual office, that’s okay!

You’re probably already wearing the right thing.

Just make sure to wear a “fun” version of your office getup. Try a pink shirt instead of a white or light blue shirt.

Go for loafers instead of dressy lace ups, and add a dash of color with your socks.

Unbutton that second button for a more laid back look.

First Date Accessories

Accessories are an excellent way to express yourself and add interest to even a simple outfit.

Plus, accessories make for great conversation starters. It’s easy to comment on someone’s watch, bracelet or earrings.

Wrist Watch

For men, the easiest accessory to wear on a first date is a wrist watch. You watch says a lot about you. The message you want to broadcast is up to you!

Are you a modern, tech-savvy gent? An Apple Watch is right on brand.

Do you appreciate a bit of analog tech in your life? A mechanical watch is perfect for you.

Maybe you have a retro streak and are into 80s and 90s nostaligia. A classic digital watch, like the Casio F-91W makes sense.

Bracelets

You can also wear a bracelet. I really like a simple metal cuff or chain.

This sort of subtle jewelry says, “I put some thought into my appearance, but I don’t mind flying under the radar.”

Should You Wear a Hat on a First Date?

Honestly? Probably not. Unless you’re doing something outside where a hat serves a function (like keeping your head warm or keeping the sun out of your eyes), a hat doesn’t really make sense.

If you’re bald or losing your hair, don’t wear a hat to cover up your head. Your date is going to see your head eventually, and covering up is a sign of insecurity.

FAQs About What to Wear on a First Date

Here are some of the most commonly asked questions about first date men’s style:

Is It Okay To Wear Jeans on a First Date?

Yes, it’s okay to wear jeans on a first date. In fact, jeans are perfect for most casual or smart casual first dates, including coffee dates and dinner dates.

Can I Wear Jeans to a Dinner Date?

Yes, you can wear jeans to a dinner date. I’d recommend fitted jeans (slim-straight or tapered, not relaxed) without any distressing or rips. Dark wash jeans are a bit more refined than light wash jeans.

What Color Should You Not Wear on a First Date?

Don’t wear all black, all white, or any crazy loud colors. Keep it simple and understated. When in doubt, remember that neutral colors always work well.

Is It Okay To Wear All Black on a First Date?

No, you shouldn’t wear all black on a first date, especially if you’re going on a dinner date. You might be confused with one of the staff!

Can I Wear Blue on a First Date?

Yes, you can wear blue on a first date.

What Should I Wear on a Winter Casual Date?

Any casual outfit will do. For example, jeans and a long sleeve casual button up shirt with boots. For outerwear, consider elevating your look with a wool overcoat instead of a bulky winter jacket.

What’s Your Go-to First Date Outfit?

Over to you now – what do you like to wear on a first date? Will you be wearing one of these outfits on your next date?

Tell us in the comments down below!