Men’s Guide: How To Dress On A First Date?

First dates are always nerve-wracking, no matter how many you’ve been to. You always have a lot of racing through your mind.

Where will you go? What will you carry? What will you talk about? And most importantly, what are you going to wear?

The venue shouldn’t be much of a biggie. As long as there is food, booze is great, and the environment is ample for communication, you’re good to go.

The same, however, cannot be said about the outfit you’ll be wearing. One wrong outfit and you ruin everything.

By now, you probably know that a good first impression will score you lots of points. So you don’t want to make it pretty obvious that you rushed into things.

And while it’s probably true that men have it easier when it comes to putting together an outfit, that doesn’t make it a walk in the park either.

If you’re reading this article, then you’ve Google searched ‘how to dress on a first date.‘ Well, I’m glad to tell you that you’re in the right place.

I’ll share with you everything you need to know about ‘sealing the deal‘ on the first date – take this from someone who has been to lots of them.

8 Important Things to Consider

Before getting deep into details, there’s something you need to know: your style is the easiest thing to change.

Not sure about your life and career path? Good luck changing that in a week. But as for style, a little adjustment in your wardrobe and you’re good to go.

The information I’m sharing is also part of the responses that I gathered from different women as research. I interviewed women of different ages, backgrounds, locations, and jobs. So if you’re here for the time, think again.

1. Effort Is Important

Effort Is Important

When a father drops his son/daughter to school, does it matter what car he is driving?

Of course not. What is important is that he arrives with his kid on time. It shows that the man is responsible and cares for the education and wellbeing of his kids.

The same principle also applies on first dates. Does it matter that you’re wearing classy designer clothes?

No. If you don’t look good then you lose it. From all the women I interviewed, none of them mentioned anything to do with designer clothes.

The most important thing on a man as per women is effort i.e. trying to look nice. It shows that you are responsible and that you care.

2. Pay Attention To Little Details

It only takes seven seconds to make a first impression. So before you leave the house, ensure that every aspect of your look is in check.

That implies ironing every wrinkle crease, thoroughly brushing your teeth, buttoning up your shirt to the right place (two to three maximum open buttons), and spraying the right amount of cologne.

Having everything on point will not only make your date appreciate your look, but it will also boost your confidence. You can be rest assured that nothing can go wrong in terms of outfit.

3. Emphasize On the Right Fit

I’ve mentioned this before and I’ll not tire to repeat it: don’t wear ill-fitting clothes.

Honestly, I’ve never understood why people insist on wearing baggy clothes. Maybe they feel more comfortable in them or maybe they grew up at a time when that was the fashion trend.

But one thing is clear, ill-fitting clothes dent your attractiveness. They make you look short, fat, and sloppy. Nothing but hard facts here!

Putting on properly fitting clothes make you look good, even if it’s a pair of jeans and t-shirts. It showcases your body’s true shape.

Editor’s Note: When I say properly fitting clothes, I don’t mean skin-tights. Your clothes should hug and not constrict your body.

4. Consider The Venue

Are you having dinner at an elegant venue or simply grabbing casual drinks at a restaurant?

The rendezvous point will have a huge effect on what you’ll wear. So plan your outfit based on the venue. Things might be a little awkward when you find yourself at a bar in a two-piece suit.

5. Shoes Aren’t As Important As You Think

I too was equally surprised by this finding. Whereas we know shoes play an integral part in a man’s outfit, it turns out that they’re pretty much all the same for women.

Probably a big reason for this is that you’ll spend more time concentrating on the upper body part than the lower one.

So, concentrate more on the trouser, watch, and shirt parts. For the shoes, a pair of boots or classy sneakers is fine. But whatever you do, don’t wear finger shoes.

6. What Time of The Day Are You Going Out?

If your date is during the day, a casual outfit will do. If it’s at night, then you might consider getting a dressier. The venues are also tied to the time.

Daytime dates call for parks, coffee shops, and casual restaurants. Night dates, on the other hand, blend better with clubs and fancier restaurants.

But this isn’t a strict rule, it’s a free world and you can dine anywhere at any time.

7. Ensure Alcohol Is Present

Yes, you can argue about this. But I’m entirely speaking out of facts. Some women agree that you don’t need alcohol to have a great first date, but a majority think otherwise. 65% of the women I interviewed voted for venues that had alcohol.

Dinner at a classy restaurant scooped the lions share at 28% of the votes, a nice cocktail was close behind at 25%, while a fun bar got 13% of the votes.

The remaining share was split between coffee and ‘strictly no alcohol’ as per some responses.

8. Consider Your Partner

Still on the same note, if you the other person is a non-drinker, then there is no point in going to a bar. While statistics might play an important role in my study, the final and most important say depends on the person you’re taking out.

Some people are introverts and would rather hang out in an isolated coffee shop. Some are intellects and will find museums and libraries more efficient. While you would love to have fun, also consider the taste of the other person.

A List of ‘BIG NO’ Outfits

A List of 'BIG NO' Outfits

Whereas there are tens of outfits you can put on to first dates, there are those that simply don’t work.

You’ll be committing fashion faux pas. And you don’t want to be the guy who bottles down all the points on the first date, do you?

So, what are these outfits that I’m talking about?

First on the list are hoods. Hoods are okay, great in fact, for the 10th or 20th date (if there’s one) but not on the first one. Hoods make you appear lazy. And as I said earlier, it’s all about making effort. A bomber jacket appears better than a hoodie.

Second, in line is sweatpants. Reason? See above. If the weather is cold, cotton chinos are an excellent alternative.

graphic T-Shirts
Graphic T-Shirts

Don’t make the mistake of appearing with graphic T-Shirts on first dates. Leave this when you’re going to your favorite rapper’s concert. An exception here is if the date is at a concert.

Next are ties. Ditch the tie and save it for a red carpet occasion. Ties will make you look too corporate and formal.

Finally, we have crocs and sandals. I don’t have to go into details of these two, do I?

What To Wear On a First Date?

After giving you a list of what not to wear, it’ll only be prudent for me to give you a list of what to wear.

Casual/Daytime Dates

1. Button-Down Shirts

These are excellent choices for first dates. They’re classy but not pretentious and they communicate through your appearance.

The weather will dictate the material of your shirt. If it’s a bit cold, put on flannel shirts. If the weather is lenient, linen shirts would be perfect.

2. Polo Shirts

Polo Shirts

While many people associate polo shirts with golf, they are actually versatile.

A polo shirt is the intellect version of a t-shirt– casual but nicer. Brands on polo shirts can be distracting, so go for those with minimal writings.

3. T-Shirts

These are the baselines of dates. Everyone wears these. But beware; t-shirts aren’t suited for all kinds of dates.

What type of t-shirt should you wear?

One that doesn’t make you look like a dork. Let the t-shirt be plain or with minimal writings on it and well-fitting (not too tight).

4. Chinos

If it’s cold outside, don’t wear sweat pants. Go for chinos instead. These are the most versatile pants you’ll come across. They are excellent for casual occasions and will also seal the deal in a business casual setting.

Another great thing with chinos is that they blend with just about any outfit. You could also opt for chino shorts if you’re going for a warm outdoor date. Nothing could go wrong with chinos.

Formal/Nighttime Dates

Formal/Nighttime Dates

You’ll need extra warmth for night dates. Here are different outfits to consider

1. Jacket

Jackets will provide you with the needed warmth while still giving you the classy look.

There are numerous types of jackets to choose from but the Harrington is my favorite. It’s lightweight, structured, and can be dressed both up and down.

Men with Jacket

The patterned linings of Harrington jackets will add the fanciness when you leave them open. Classic leather jackets are also excellent alternatives to these.

2. Sweater

What could possibly go wrong with wearing a sweater to a date? Sweaters are warm, versatile, and give you a simple but classy impression.

Moreover, you can style up a sweater with any combo you like, whether with a blazer or Oxford Cloth Button Down (OCBD) shirts

3. Blazer

While blazers are considered to be formal, you can get creative and wear them with smart casual outfits. You can wear a blazer with a dress shirt or OCBD shirt. If the weather is cold, exchange the shirt with a sweater.

4. Dress Pants

If you’re headed to a fancy restaurant, you might want to upgrade your chinos to dress pants. a pair of linen or woolen trousers will do the trick. Go for the basic neutral colors, nothing too flashy.

5. Dress Shoes

For the footwear, it’s safe to lean on the formality side. This isn’t to cancel out sneakers, but you definitely don’t want to show up with your dirty worn-out chucks. Oxfords are perfect for a casual date. But if you want to scale things down a little bit, other options include boots and loafers.

Boots are versatile while loafers are for guys with a sporty or preppy taste. If you opt to go with sneakers, aim for minimalism. Simple black or white sneakers with a sleek silhouette will go with most outfits.

Pro Tips: The Do’s and Don’ts


  1. Always wear a watch. It doesn’t have to be expensive, but catchy. One with a metallic strap for fancy dinner or a sports watch for a casual daytime date. A watch makes you whole and complete.
  2. Put on quality underwear, just in case things escalate to the bedroom. You can imagine the embarrassment of getting caught in old, stretchy, flimsies whities.
  3. Lean more towards neutral or dark colors: black, gray, navy, and white. These give you a sophisticated look. Your date will focus more on what you’re saying rather than what you’re wearing.
  4. Cologne or perfume. But don’t overdo it. A simple spray inside your shirt and near the neck is enough. Smelling good is equally important to looking good.


  1. Hoodies top my list. Wear hoodies everywhere else aside from the first date. You want your date to know that you put effort into meeting him/her. If the weather is cold and you must put on something warm, a denim jacket, trench coat or cashmere sweaters will work the trick.
  2. Open shoes. You might have passed by the spa for a quick manicure, but no one wants to see your toenails. No matter how casual your date is going to be, leave behind your open shoes. Instead, opt for moccasin or driving loafers instead.
  3. Hats and sunglasses (especially indoors). Having these two on will make your date suspect that you’re hiding something. Sunglasses make you unapproachable and non-revealing. I’m sure your date wants to know you both inside and out.


The first date might be the beginning of something beautiful and long-lasting. Therefore, dress for the occasion. Let your date know that you’re serious.

When the outfit is perfect, everything else will follow. Don’t forget to take the time worthwhile. Take her to a fun place and have a great time.

To You! What have you decided to wear on your first date?

About Austin Green

Austin Green is the co-founder of Men Glow Up. This guy is obsessed with Men's Grooming and Fashion. I mostly publish tutorials, advice, and buying guides on Beard Care Products. Follow me on my channel Twitter. (No Spam, please :))

Leave a Comment