The Ultimate Men’s Fashion Guide: What To Wear On A First Date

Posted by Sage, January 17, 2019.

So you’re finally going on a date with that cute girl you met last week. To maximize your chances of it going well, you have to look your best. However, a lot of guys don’t feel comfortable exploring their fashion style since it makes them feel less masculine. They’re likely set in their ways and don’t like to stand out. If this sounds like you, you’re going to have to overcome this mental hurdle, because whether you like it or not, we’re all judged on our appearance.

While fashion might sound complicated, it’s really not, once you learn the basics. To create the best first impression, you have to make sure you’re looking your best. There are a few rules for this:

1. Proper grooming
2. Fit
3. Match & Coordination
4. Overdressing & Underdressing
5. Dress to match your personality

We’ll go through and break each one down, one by one:

Proper grooming

Proper grooming includes showering, cleansing, and shaving. A shower cleans you up and energizes you for your date. I highly recommend taking a cold shower which gets the blood flowing and gives you an energy boost. Also, make sure to use a facial cleanser. While many guys may think that face cleansing products are only for women, men should use them too. I personally like Garnier, but there are tons of options. A facial cleanser help to keep your skin clear, smooth and looking young.

Don’t forget to shave. Going unshaven will communicate to girls that you’re a slob or just don’t care enough about the date to shave. Also, some girls are sensitive to stubble so you want to shave in case you kiss. If you’re one of the guys with a beard make sure to trim it. This includes your nose and ear hairs as well. The last thing a girl wants to see is a bunch of hair sticking out of your nose or ears as you guys are talking. If it’s been a while since you had a haircut, visit your barber as well.

Wear clothes that fit

When it comes to clothes, the fit is the most important. Most guys make the mistake of wearing clothes that are too loose which makes them look that they’re still in high school. There’s a good chance that a lot of your current clothes are too big. You can have the nicest clothes but if they don’t fit properly, you won’t look good.

The first step is to go through your wardrobe and get rid of anything that fits poorly. Be ruthless. If you’re not sure about your measurements, get yourself measured by a tailor.
Here are some quick tips to follow:

Shirt: The fit should be snug yet comfortable. The collar of the shirt should gently hug your neck without constricting it, and the shoulder seam should line up with your shoulder bone. For dress shirts, the cuff should meet the point where your wrist bends.

Blazer: For blazers, its length should cover your ass. The shoulder line should be smooth and there should be no folds if it’s buttoned up. If the blazer pulls across the chest or pulls across the shoulders when you fold your arms, it’s too tight. A good way to tell if its is too tight is if there an “X-shape” around the button when buttoned up. There should be no folders or bunching whatsoever. The blazer’s sleeve should extend just beyond the wrist bone. You should easily be able to fit your flat hand inside the blazer
Pants: Your pants should stay on your hips without a belt. This includes jeans. If it starts slipping off, it’s too big. Most guys wear pants that are too big and usually feel uncomfortable wearing their first pair of properly fitted pants. They should feel a bit tight which is normal. The pants should be close to the leg but not so tight you can’t move.

At most, you want a single break in your pants. These are the natural creases found at the bottom of your pant legs. If your pants get stuck under your heels, it means they’re too long. But if the pants rise up and expose your socks while walking, it means they’re too short.

Matching and Coordination

Most guys have no idea on how to match and coordinate their clothes. But it’s pretty easy once you know the basics:

For your shirt, a collared one is generally a safe option. It doesn’t matter if it’s a dress shirt or polo, as long as it fits well and is comfortable. A light-colored shirt generally goes better with lighter pants and a dark-colored shirt goes better with darker pants.

For pants, dark jeans, khakis or dress pants are a safe bet. If you’re wearing dress pants, they should match your socks. And if you’re wearing jeans, your socks and shoes should match.

If you want to dress things up, a blazer or suit jacket works well for most occasions. But if you do wear one, don’t wear a suit or tie. It’s a date, not a business meeting.

For accessories, make sure that your belt and shoes match. Watches are great, but make sure that it matches the rest of your attire. For example, if you’re wearing a blazer, don’t wear a sports watch.

Lastly, we move on to shoes. While running shoes may be comfortable, don’t wear them for a first date. Stick with leather shoes. Whether they’re casual or dressy, it’s fine. Just make sure they match your belt.

If you’re not sure where to start, the easiest way is to go out and buy a “black set” and “brown set”. Your black set will consist of a nice black jacket, a black belt and a nice pair of black shoes. Your brown set will consist of a nice brown jacket, brown belt, and brown shoes as well.

Then pick up a couple pairs of designer jeans and about ten shirts. Then it’s all about mixing and matching.

Pick a nice shirt and pair of jeans to go along with your black or brown set. Whatever you think looks better. Personally, I like to wear lighter shirts with the brown set and darker shirts with the black set.

Overdressing or Underdressing

Because it’s the first date, it’s important to keep things light and casual. Don’t wear a three-piece suit. This isn’t a job interview. Again, your safest bet is to stick with a collared shirt, dark blue jeans and a blazer.

On the other hand, you don’t want to be too casual either. Leave the wife beater and running shoes at home. You want to make a great first impression on your date but don’t want to look like you’re trying. The key is to strike a balance. So unless you’re planning to hike or do some sporty activity, stick with dress shoes.

Dress to match your personality

Whatever you decide to wear, it should ultimately match your personality. If you’re a 50-year old business man who wears a hoodie and baggy shorts, or a 20-year old student who wears an expensive 3-piece suit, there’s going to be a mismatch.

If you’re not dressing to match your personality, it’s not going to be fashionable. And you won’t be happy either. So if like rock n roll, you should dress along these lines. Or if you’re a successful businessman, you should be dressing like a successful businessman.

Start looking through magazines or browsing through the internet to get ideas. Find fashional people who are similar to you and emulate their fashion. I like to check out what the mannequins are wearing in clothing stores to get ideas.

And if you’re still having trouble with your fashion, get a female friend to take you out shopping. But be sure that she has a good sense of fashion. Just because she’s a woman doesn’t mean she knows what’s looks good on a man.

If you’re looking for more in-depth fashion advice, check out our image & fashion product reviews specifically tailored for meeting and attracting women.

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