How to Dress on a Date

Hi guys, this is Nicolas.

In my first post, I was addressing athletic guys’ issues when it comes to finding clothes that fit. Today, Greg invited me to write you a post about how to dress for a date or when you’re trying to meet girls.

In this post, I’d like to provide you with good-to-go field knowledge that will brush off forever the anxiety of dressing well for a date.

We’ll have a quick look at why it’s important, the results you can expect, the traps you don’t want to fall into (that’s the foundation because it’s about your mindset) and of course the meat and potatoes with some tips and outfit examples.

Ryan Gosling Clothes

No worries, it’s not about dressing up like someone you’re not, like a seduction coach or a tacky PUA…

Why you should care and what to expect

It’s extremely important for a man to dress well for a date.

But do you know why? I’m not a seduction expert, but dressing well is a display of high status and that’s a great driver of women’s attraction.

Dressing well and looking smart means that you are putting forth a great first impression. Your date will judge the clothes you wear and the way that you look. While that may not seem fair to your intellectual self, it’s the way it works so you need to be prepared and look the part.

The results?

By dressing up for a date you send a strong signal of confidence. Moreover, your date will be pleased that you took the time to dress up and look sharp for your night out. Of course, dressing well, makes you look good but it also shows your date that you care about the time you’ll spend together. When you dress well, not only do you look good, but your date feels good as well. You’re preparing the ground so that both of you can have a nice night.

Mistakes men make that you’re not allowed to repeat

The biggest mistake would be to show an obvious lack of care in your outfit and grooming. It’ll be perceived right away by the sharp eyes of your partner. Needless to say, you’re not making things easy for yourself.

1. Look Fresh

First of all, you’re not allowed to show up sloppy with your clothes wrinkled. Showing a huge lack of care would make your date feel uncomfortable and probably disrespected. Your clothes need to look fresh and clean. For this reason, it’s practical to keep the items in your wardrobe neat and ready to wear for any occasion. Have at least one shirt ironed as well as a pair of pants. If this is too time-consuming, drop them off at the dry cleaner’s every week. Shine your dress shoes once in a while.


Freshing up. You don’t have to do it like that

2. Look smart

Second huge error to avoid: An easy mistake to make is to not think about the image your clothes reflect. Ideally, you’ll need to go for simple items that don’t say too much about yourself and don’t immediately place you in a box.

There is an infinite number of clothes that would look weird on a date and I can’t list them all. I’m trying to give you a rule of thumb here.

The way you dress is a huge indicator of the person you are. You don’t want to make a bad impression on first sight.

Wearing really bright colors, clothes that don’t suit your lifestyle or, quite simply, ‘fun’ hats and shoes, generally projects an image that is more likely to break you than to make you.

Women like guys who dress well. Dressing like a teenager, a geek or a cheap playboy…just doesn’t cut it.

3. Dress up a bit from your standards

Dressing well for a date is something that takes just a bit of thought. You can’t just throw together an outfit at the last minute and expect to look good. At least not the first time.

In my opinion, the most important thing to keep in mind is: Always dress a step up from what you would wear if you were going out with friends. For example, if you are going to a movie think about what you would wear if you were going with friends and then dress slightly nicer.

Going to a restaurant? You don’t want her to notice the guy that sat next to your table because he looks better.

Ok so what should I wear?

Quick sum-up: you now know two things. You want to dress up a little bit and pick clothes that won’t ruin your plans because of the image they project.

In concrete terms, what can I wear to satisfy these two criteria?

It’s quite simple as you’ll see.

Back to basics

Once again, everything comes down to mastering the. As a reminder, the basics are :

– Simple colors: blue, grey, white and brown

– Simple designs: no patterns, prints or extravagant seams

– Well cut for you shape and size, in the right size

And as you’ll want to make a bit of an effort and dress a bit more formally…

An example of an outfit would be: a grey jacket, a white shirt, a dark blue pair of raw jeans and a pair of brown derbys.

Neil Patrick Harris Clothes

The huge advantage of items that satisfy these criteria is that you can wear them all together with no problem. You can’t go wrong.

If you think it looks a bit sad, rest assured, it really isn’t the case. An example of a really sad outfit isn’t that, it’s rather something monochrome black or grey.

A little detail: These items and colors can easily be mixed together to create really effective outfits. Marine blue blazer, jeans or grey trousers, white or sky blue shirt.


Justin Timberlake Clothes

That’s as dressed up as it gets. Remember to dress according to YOUR date.

Placing the marker where it should go

Now you need to play around with the formal nature of your outfit. Go for something that is suitable for your date. You want to make an effort but you don’t want to look like you’re going to church in your Sunday best…

Above I gave the following example of outfit:

A grey jacket, a white shirt, a dark blue pair of raw jeans and a pair of brown derbys

If that seems too formal to you, get rid of the jacket. If you want something more formal, add a tie. You can also go for a shirt and tie with no jacket. Or even a casual chambray shirt or a T-shirt under your jacket if you’re looking to get a bit further away from formal.

You can replace the derbys with a pair of desert boots. Or even casual sneakers. But be careful, I’m not talking about a dirty, smelly pair of old running shoes. Subtle sneakers that are in good form will do the trick.

style to attract girls

Blue shirt, slightly faded jeans and sneakers for more of a casual outfit. If your date is casual, it’s not bad!

One last thought

A chef always tastes what he’s cooking before putting it on the plate.

It’s always a good idea to lay out your clothes the night before a big day and make sure everything fits and flows together.

Don’t be afraid to try on several outfits and actually look at yourself in the mirror. You can also ask a trusted friend for advice.

A key point to remember is that if you are unsure if something looks good or not, it probably doesn’t look that good. You should rather wear a safe outfit than take a useless risk.

Final Comments by Greg O’Gallagher

Building an absolutely chiseled physique, while awesome, is not enough on its own! In fact, I know plenty of fit guys who dress completely tacky and get very little attention because of it.

When you build an incredible physique and supplement that with dressing with ‘effortless style’ you begin to stand out and people become very, very intrigued. My advice is to put a little work into how you dress and reap the rewards in your dating life, work-life and more.

If you want a great course on how to dress with style and how to create outfits that look downright amazing then I’d recommend style for the modern man (note: this is an affiliate link so I get a commission if you buy the course).

That said, I only promote courses that I wholeheartedly believe in and have received value from myself. I originally purchased Style for the Modern Man when it first came out a couple of years ago and it has helped immensely.

Here we help men choose items of clothing and put together simple, yet stunning, outfits.

Have a look at the blog or take our free