What to Wear on a First Date: A Man’s Guide

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by  William Barton | Last Updated: 

This one’s easy:

Velvet suit. Jewel encrusted cane. Massive signet rings. 

You meet her at the local Jamba Juice, hold your hand out, and say “kiss the rings.” Get a smoothie, enjoy the date. The rest, as they say, is history. 

Ok, obviously that’s a joke (you knew that, right?). 

But picking your outfit for a first date can be tough. You want to make a good impression on her, but you don’t want to look like you’re trying too hard. 

You want to show a bit of your personality, but you don’t want it to be too relaxed. 

Don’t worry. No matter what your personal style is, there are plenty of outfits you can put together to impress her without looking like you anguished for hours over your style. 

Building the Perfect First Date Outfit

As a men’s fashion writer, I don’t pull these style rules out of a hat. I’ve asked dozens (if not hundreds) of women what their favorite things to see on a guy is, and while I’ve gotten a few left-field answers (eyeliner? really?) there are a few answers that stand out over and over again. 

I’m going to break down your perfect first date outfit piece by piece so you have the best possible chance to impress her. 

The items in the sections below are a great place to start. For specific dates (like going to a bar, or meeting for coffee), I’ve outlined how you should scale your outfit up or down. 

A tux isn’t going to knock her socks off if you’re meeting her for a bagel. So without knowing what legendary first date you have planned, we’re going to start with the basics. 

On Top

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Your surest bet on top is an Oxford cloth button down (OCBD). It’s such a versatile piece in that it can be styled in so many different ways. 

Darker colors are usually the most flattering, so a nice navy or black button down shirt is a great way to go. 

Outfit 6 Frank and Oak 2

If your date is a casual lunch occasion, you can leave the OCBD unbuttoned with a t-shirt underneath. Try rolling the sleeves up twice to show off those forearms, too. Most women find men’s forearms sexy. So anything you can do to set those puppies free is in your best interest. 

That said, don’t casually roll your sleeves if it’s freezing outside. And if you have noodle arms, you may want to beef them up a bit before you set the pythons loose. Here’s a handy guide to help you jack those forearms up

Leave the shirt roll below your elbow. You don’t want it at or above because you lose a bit of the mystique, and the rolled fabric accentuates and forces more bulk into the bit of muscle you’re showing. 

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If you’re doing an evening date (or just don’t like the layered t-shirt and OCBD look), leave the shirt buttoned. On cooler evenings, throwing on something simple like a bomber jacket is a fantastic choice. But if it’s warm outside, still roll those sleeves and stun her with those husky man-wrists. 

Now if you’re an athletic and fit guy, I hope you haven’t been getting lazy with your style. You always look incredible with just a t-shirt, so you may not put in more effort for a date. But that’s a huge mistake. If you wear something nice like a crisp oxford shirt, tucked in, you’re playing on the next level. Fit and stylish? You’re a total catch. 

As you can tell, I’m partial to the oxford button down shirt for nearly every first date. There are a few exceptions for specific types of dates, but I’m going to cover them later. For now, just know that a good OCBD is your best friend, no matter what your body type is, and it’s appropriate and stylish for just about any date situation. 

Accessorize

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You might think the second most important item to consider for your date night is your pants, or maybe your shoes. But you’d be wrong. While those are important, your accessories catch her eye more than you’d think. 

The most commonly accepted form of men’s jewelry, and one of the best ways to subtly express your personality, is through a nice watch.

The watch you choose for your date should be masculine, stylish, and a little unusual. 

Vincero Outrider closeup dial

If you’re going casual, I’m a big fan of the Vincero Outrider. At 40mm, it’s large but not oversized. You don’t want to wear anything larger than 44mm in diameter. When your watch is too big, it can either dwarf your wrist or make you look like you’re trying too hard. 

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But 40mm is the perfect balance between strong and masculine, without crossing over the line into “hey, did you see my watch? I feel the need to try and prove myself to everyone.” 

For dressier dates like a cozy cocktail bar, a classic automatic like the Vincero Icon is a better pick. With a steel link bracelet and a handsome refined dial, you’re showing you have class without going over the top. 

Again, the Icon has a 40mm dial, so it’s a flattering size, and the silver accents bring her attention to your hands and forearms, two areas women just seem to love

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The key with accessories is to stick with your personality. If you don’t feel comfortable wearing a bulky signet ring, skip it. Above all, you don’t want anything to look out of place. But a nice belt that matches the color of your shoes and watch shows you’re a man who pays attention to the details. 

And if the mood strikes, leather bracelets or even a metal cuff can also draw attention to your masculine attributes without looking misplaced. 

On Bottom

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Most guys who are new to paying attention to their style have a pretty limited selection of pants to choose from in their wardrobe. There’s a lot of variety, but it might not seem that way if you’re just getting started on your style journey.  

Reach for your crisp jeans (no holes or distressing, and hopefully in neat indigo or black) or chinos on a first date. Chinos are a safe bet, as they dress up or down depending on what they’re paired with. I personally like jeans, but for a first date, wear your nicest pair. 

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Don’t bust out your distressed jeans on the first date. Instead, go with the crispy deep blue jeans you might save for a Saturday night, even if your date is during the day. 

Because jeans are inherently casual, you can wear your most formal-looking pair and still avoid looking up-tight. 

Stay away from more casual pieces like joggers and workout shorts unless the date calls for it. If you both met at the gym and your first date is a post cycling smoothie, then workout apparel makes sense. Otherwise, play it classic. 

Whatever you do, don’t wear your ratty old cargo shorts. If there’s one thing all women agree on, it’s that cargo shorts are terrible.

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If your date is on a hot summer day and you need to ditch some fabric around your legs, try a pair of simple, classic chino shorts. 

Fit is the key for all bottoms. Your pants shouldn’t be baggy, nor should they sag. I always recommend a slim fit, even for huskier gents. You’d be surprised at how few guys understand the principles of well-fitting clothes, and because so few guys do, women go crazy for guys who get it. 

Seriously, just wearing a pair of pants that fits well sends a signal to your date that you’ve got control over at least one aspect of your life. And she’s going to dig it. Many guys don’t dress well, so you should take advantage of that and blow other dudes out of the water with your understanding of style. 

On Your Feet

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Your shoes will bring your whole outfit together. In fact, a study suggested that 64% of women judge a man’s shoes—and you better believe she’s scoping out your footwear on the very first date. This is the hardest part to nail down because your footwear determines the formality of your style. 

Consider this: if you’re wearing a oxford shirt, chinos, and a pair of dress shoes, you might look like you just clocked out and are on a break from the office. But if you pair the same top and bottom with a pair of white minimalist sneakers, suddenly you look refined, chill, and put together. 

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If I had to go on 100 first dates and could only pick two pairs of shoes for all of them, I’d go with a white dress sneaker and a pair of brown city boots. 

KOIO Capri Triple White

The KOIO Capri Triple White is as loud as a white dress sneaker can get without leaving the minimalist realm. Go for these if you want a pair with a lot of details that aesthetically sits in between the dress and athletic sneaker worlds.

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Bust your white dress sneakers out for any daytime date. They should match any color combo you have on top, and if you keep them clean, you’re expressing your ability to care for the things in your life. 

And a well cared-for pair of brown boots is a solid play for just about every evening date, assuming it’s fairly casual. Boots match well with both jeans and chinos, and like white sneakers, they blend with whatever your personal style is. 

What Should I Wear to a Bar?

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The bar is one of the most common first dates, so it deserves a special mention. And while this next tidbit isn’t style advice, I think it’s important: don’t take her to a dive bar for a first date. You should know of a nice cocktail bar in town, and that’s where you should go. 

Having a drink in hand will take the edge off for both of you, but a nice lounge is fun, inviting, with a bit of sensual edge. Just make sure to limit yourself to two drinks—an SIA study found that 70% of women don’t like it when their date goes for drink number three. 

vintage old fashioned bourbon cocktail

If you’re not sure what to order, a cocktail like an Old Fashioned is always a solid choice. It’s gentlemanly, and it likely won’t be the go-to order for most guys she’s been on a date with so it’ll be an interesting talking point for her. 

My go-to date night at the cocktail lounge outfit goes like this:

  • Clean white t-shirt
  • Fitted leather jacket
  • Crisp dark blue jeans
  • Brown boots
  • Classy but casual watch

It’s a simple outfit, but a killer combo when you pull it off correctly. But you need to consider the finer details. 

Make sure your white t-shirt is ironed and stain-free. No wrinkles, and no stray mustard stains. If you don’t have a shirt like that, either get one, or go the oxford cloth button down route. 

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The fit of the leather jacket is crucial here, too. It should taper through the torso and not add too much bulk to your top half. Don’t put on your dad’s leather jacket—the one he took on motorcycle rides. You want something slimming and dapper. 

If you’re not feeling the leather jacket vibe, or you’re not sure you want to invest there yet, opt for a fitted blazer. Keep it simple with a dark navy, but try to avoid black, which is a bit too formal looking.

Your boots should be clean. Not the job-site kind. Not the boots you wear for yard work. But the boots meant for hitting downtown on a Saturday night. The best choices are dress boots and Chelsea boots—they’re both sophisticated, but have plenty of masculinity, too. 

And lastly, the watch you wear is going to catch her eye. Having a watch or two (or if you’re like me: 20) shows an appreciation for the finer things. For this leather jacket outfit, I recommend something a bit dressier, but still masculine and bold. I’d finish this outfit with the Vincero Icon

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The Vincero Icon is a statement. The Seiko automatic movement, sapphire crystal, and hefty water resistance are all packaged in an affordable and dressy timepiece. If you had any doubts that Vincero is commited to quality, let the Icon put them to rest.

Check Best Price Read Our Review
If you click this link and make a purchase, we earn a commission at no additional cost to you.

The silver and navy with the link bracelet has that boardroom formality to it, but because it’s a bit larger at 40mm, it’s still casual and plenty masculine. 

What Should I Wear to a Coffee Date?

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The coffee date is a completely different vibe than the cocktail lounge date, so ditch the leather jacket or blazer and keep your outfit relaxed while minding critical details like ironing. 

My ideal coffee date outfit looks something like this:

  • Oxford cloth button down shirt, buttoned up with the sleeves rolled three-quarters
  • Slim fit chinos
  • Clean white dress sneakers
  • Casual watch
  • Optional if it’s chilly: a slim fitted bomber jacket

This is the perfect coffee date outfit because it comes off as very relaxed, but it’s also clear that you’ve made an effort (but not too much) to look nice. 

Keep the OCBD untucked to avoid crossing into business-casual territory. Fit is everything with this outfit. If your shirt or pants are too big, you risk looking like you raided our dad’s wardrobe. 

If the weather calls for a jacket, a clean-cut bomber is a solid choice. Because this outfit is so simple, add dashes of personality through your accessories. I like military inspired watches, so for this one, I’d bust out the Vincero Outrider. Metal cuffs and leather bracelets also work well with this outfit. 

Like I said up top, because you’re going all-casual here, you must make sure you’ve ironed or steamed everything. If you wear a wrinkled shirt with wrinkled pants, you’ll look like you just rolled out of bed. But when these items are crisp and neat, you come across as mature and self-assured. 

3 Style Rules You Must Follow for Your First Date

1. Confidence First

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Really, you’ve read this far because you understand something very basic about dating: your confidence is the key. 

Yes, I believe an awesome outfit can boost your confidence. But I also know what it feels like to put on a set of clothes that doesn’t really fit my personality. 

If you’re reading through this and thinking that chinos and an Oxford shirt don’t really meld with your personality, I’d first challenge you to give it a shot. But if it’s really not working for you, swap out one thing at a time. Maybe switch out the chinos for a crisp new pair of jeans. Feeling a little more yourself? Good. Then that’s your first-date outfit. 

Whatever you choose to wear should add to your confidence level, and never detract. If you get simple pieces that fit well, there should be nothing holding your wonderful personality back.

2. Fit is Everything

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As a 30-year-old guy, my friend group is pretty evenly split. About half the dudes dress like they’re in their early 20s, complete with ripped baggy jeans and band t-shirts, and the other half have girlfriends or wives.

You might think a girl is cute even if she’s wearing a baggy old shirt and a pair of sweats, but I’d bet she’d be even better looking with some clothes that fit her well. If you feel the same way, then there’s no reason you shouldn’t do the same. 

Make sure the shoulder seams of your shirts line up with your shoulder bone (not the end of the muscle). The sleeves should fall at your wrists, but not any further. Get a pair of slim-fitted pants, and wear them up at your waist.  

Once you’ve got the basic principles of fit down, you can look incredible in just about anything.

And if you’re a huskier guy, don’t think the rules of fit don’t apply to you. Too many heavier guys think they need baggy clothes to hide what they have going on, but it’s time to ditch that mentality. 

Slim fits aren’t just for skinny dudes. Big guys can rock fitted clothes and get the same confidence boost (and hence attention from the ladies).

And if you’re hitting the dating world hard and have several first dates already lined up, consider investing in a few quality clothes and taking them to a tailor. The feel of a custom-fitted shirt is enough to make any man confident, and is another way you can separate yourself from the pack. 

3. Cleanliness is Next

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Obviously you should wear clean clothes on your date. But this style rule goes a little deeper. I mentioned it several times through the article, but the cleanliness of your accessories (particularly your shoes) makes all the difference. 

If you’re wearing white sneakers, make sure the white leather is squeaky clean. Get a toothbrush and dish soap, and suds the white rubber sole (not the bottom, but the sides). 

A woman’s first impression of you takes place in a matter of seconds. And while she may not consciously notice your shoes right away, there’s no doubt that those seemingly minor details add up to a better impression.

And the same goes for your top. Steam or iron your shirt, and make sure it’s lint-free. Again, she might not consciously note it (though, so few dudes do this extra step, she might).

The more attention to detail in your outfit, the better the first impression.  

3 Huge Style Mistakes to Avoid on Your First Date

1. Graphic Tees

Graphic tees are made for middle-schoolers trying to discover their personality. 

It’s a widely known fact among women that any guy wearing a graphic tee is basically saying, “I need someone to take care of me.” And nobody wants to sign up for that.

If you’re 24 or older, it’s time to throw away your graphic tees. I’ll make exceptions for one or two of your favorite band shirts. But toss the rest. 

Needless to say, if you shouldn’t be wearing a graphic tee at all, you certainly shouldn’t be wearing it on your first date. 

2. Holes

Even if you’re going to the cool new cocktail bar across town, avoid wearing anything with holes in it. We’re mainly talking about jeans here.

Some guys can pull off distressed jeans (though I steer clear). But it’s usually a younger style for guys in their early and mid-20s. I know a few dudes in their 30s (and even their 40s) who look awesome with ripped jeans, but they’re also incredibly handsome, fit, have tattoos, and rock impeccable beards. That’s a very small percentage of the population. 

In general, guys who are either in their 30s or approaching should opt for crisp blue or black jeans over anything distressed. Especially on your first date. They can only “lose” you points, and you never want to play that game on date number one. 

3. Wearing What You’d “Normally” Wear

Man with shiny shirt and fedora pointing to himself and smiling 2

One of my best friends wears a graphic shirt, baggy jeans, and flip flops whenever he’s not at work. And that includes dates. 

He’s single.

And honestly, I can’t get him to see the value of wearing nicer clothes, at least for the first date. The dude is a total catch: good looking, super outgoing and friendly, great conversationalist, solid professional job. But he wears a shirt that says “I do my own stunts,” a baggy pair of jeans, and flip flops to his dates. 

And his excuse is “I want a girl who likes me for me, not for my clothes.” Which I understand. And I agree. 

But get this: he’s a lawyer. And when he walks into the courtroom, it’s a necessary part of his job to be taken seriously. So he wears a pressed suit and tie (it’s still too baggy, but whatever). Sure, he could win a case wearing flip flops, but his ragged clothes aren’t going to be a point in his favor.

While dating isn’t a job, per se, it’s important to go into a date with the same mindset. And if that doesn’t help, here’s another way to think about it: wouldn’t you want to date a woman who has the self-respect to date a man that puts some effort into his looks? If your girl has low standards, what does that say about you?

Sure, you don’t want to be with a woman that’s superficial. But there’s a huge gap between superficial and not wanting to date a man-baby.

Set for Success

From your initial swipe right, dating is essentially a process of information gathering.And your style conveys a heck of a lot of information. If you want to attract quality women, you have to dress the part. 

These style rules are great for first dates, but they should also apply for your everyday life. If you pick up a few of these clothing pieces, you won’t ever have to think about what to wear on your first date again. You’ll have no choice but to look dang good. 

Now all that’s left is to figure out where to take her. But don’t worry, we have 30 amazing date ideas right here.

FAQs

What color should a man wear on the first date?

Black is an excellent choice for the first date. It’s neutral, slimming, and masculine. Don’t go overboard by dressing all black—you don’t want her to think you’re goth. But a black shirt over blue jeans is a classic combo that ticks all the style boxes.

Are jeans OK for a first date?

Jeans are perfect for a first date, provided that you’re not going to a formal soiree. Just don’t wear distressed jeans—a nice, crisp pair of denim is ideal.

Who pays on the first date?

The person who initiates the date should assume they’re paying. So if you asked her on the date, you should be ready to pay unless you’ve agreed otherwise beforehand. The lines are a bit murkier if she initiated the date. In any case, you should be mentally ready to pay the bill and then adjust according to the moment. You don’t want to get caught being surprised that you’re paying—not a good look.

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