Studies show significant decreases in sexual activity among people all over the planet. This includes young men. Now, there (usually) is some period of time between a first date and getting to the business, and first dates can be the initial step to something more meaningful than just a quick fling. Making the most of your first impression is the key to getting to the next step. The biggest part of the first impression is knowing what to wear on a first date as a man.
While what you wear is important, it’s actually not the most important thing. Remember, broke musicians and artists tend to be much more successful with women than your average man, and it’s not necessarily because they dress well. These guys have interesting lives and bring a lot of excitement, passion, and personality to the table.
Dressing well does provide the foundation for your personality to shine, but your personality must do the heavy lifting after the first impression. Keep this in mind as we go through the article.
Knowing what to wear on a first date as a man will signal three major things:
- Confidence
- Intelligence / awareness
- Resources
Confidence
The confidence you exude will make the biggest difference on how well your date goes. A man who dresses appropriately, looks put together, and can balance his outfit is a man who projects security, maturity, and confidence. Being able to pull off an appropriate outfit signals the minimum level of confidence women expect. This will put your date at ease.
Dressing well will also make you feel more confident, which should allow your personality to shine more authentically. Don’t use your clothes to hide from insecurities. Instead, let your outfit be a sign of your swagger.
Intelligence / awareness
A more subtle signal, but an important one nonetheless. Dressing appropriately for the occasion signals a certain level of intelligence and awareness. Knowing what to wear on a first date as a man makes you look smart.
If you were to show up in a three piece suit for a casual weekend lunchtime date at a local café, for instance, being overdressed would show that you are unaware of your surroundings and the appropriate level of dress for the situation. The same thing would apply if you showed up to a high-end restaurant in running shoes and dad jeans. Either would make your date uneasy, which is not a good sign for the outing.
We’ll discuss different outfit ideas for different date types later in the post. The key is to use common sense and match or go maybe slightly dressier than most of the people are at the date destination.
Resources
Women judge your resources by your attire. This doesn’t mean you need to look like you’re rich. Even if you’re broke, that’s ok (and you certainly want to avoid a woman who is only interested in money, although women are entitled to their standards too). Resources refer to more than just money.
Signaling that you have resources doesn’t mean you have to flex like you are rich. Which is bad even if it’s the truth. It’s more about do you have the minimum necessary resources to dress well for a date. Anything on top of that is a bonus.
So even if you’re broke, you should at least be able to show that you’re able to put together an outfit that is clean, stylish, and appropriate for the occasion. If you cannot do this, then you need to focus on yourself before you start dating seriously.
What to wear
What to wear on a first date as a man will depend on the type of date you have set up, as well as your own personal style. Usually first dates range from casual (i.e. coffee) to dressy casual (i.e. art exhibit, nice dinner). Other date ideas, such as a hike or workout class, will require different attire, but you still want to look good.
On a related note, you want to keep your first date in either the casual or dressy casual territory. These are the most comfortable situations for the majority of people, and it will allow both of you to relax and focus on getting to know each other.
Trying to overly impress a first date by taking her to an overly lavish restaurant requiring very dressy attire, for instance, can be off-putting. It can make you seem too forward or like you’re trying too hard. This added pressure won’t help you out. Exception: if you actually are well-off and frequent certain spots like this, it can work if you’re very comfortable there (it helps to be on a first-name basis with the bartender). The key is staying in your comfort zone too.
On the other hand, taking her to a run-down dive bar for two dollar beers sends the wrong signal in the other direction. It shows that you’re either cheap or are not taking her seriously. Neither is a great message to send if you are dating to find a serious relationship (these types of places can be fun if you’re not looking for something serious, but that’s a whole other discussion).
Casual
Casual dates include coffee, lunch (these two are very casual and almost not considered a “date”, but some people like these as a first step), drinks at a cocktail or wine bar, low-key dinner, live music, a movie, a sporting event, some kind of class or activity, etc…
For these, the template is simple. Go one notch up in dressiness from what you would wear to the same place when you are not on a date. This keeps you looking good but also comfortable in your attire. Make sure your shoes and clothes are clean and fit well.
For instance, if you’re meeting for a drink at a cocktail bar that you’ve been to, and you usually wear jeans, chukka boots, and a t-shirt, you could go with chinos, a polo shirt, and chukka boots. Or dark denim jeans, chukka boots, and a casual button down. If you have a nice watch, wear it (but not a smart watch, keep it classic). Below are some examples.
If you’re trying something out of your comfort zone, like an art class or wine tasting or something you’re not used to attending, then try to find some pictures of the place and match the general level of dressiness. You can always call the place and ask too.
Important note, for casual dates you should stay within your aesthetic zone. If you tend to wear more rugged attire (jeans, workwear boots, flannels), then wear a cleaned up version of this (dark denim, clean boots, plain t-shirt, and a shirt-jacket). Apply this principle to your personal style. You definitely don’t want to feel like a phony wearing something you normally wouldn’t.
And make sure to wear good shoes. Women always notice this detail. If you need more advice here, check out this article.
Dressy casual
Dressy casual dates consist mainly of nice (but not too expensive) dinners, a concert, a show (theatre, opera, etc…), an art exhibit, or something along these lines.
You can go with a sport coat for these occasions (maybe not a concert… depends on who you’re seeing). This piece enhances your overall appearance, and is not out of place in these situations. But only wear one if you are used to wearing them at least semi-regularly.
You can match the rest of your outfit depending on the situation. For a decent restaurant? You could swing it with some nice dark denim, some dressier boots, and a button down. Or with chinos, loafers, and a polo shirt or button down. Dress slacks and a dress shirt are probably too dressy, but it could be appropriate for some dates (maybe a show or art exhibit, or something after work).
Below are a few ideas. You have more room for creativity than you think with a dressy casual outfit. Even if you’re style leans less traditional. And don’t be afraid to add some color – you don’t have to stick with the business blues and greys.
And if you have a non-traditional style, wear the nicest version of your normal casual aesthetic. For our rugged fellows, it could be dark jeans, dressy boots, and a leather jacket or suede bomber. For our t-shirt and jeans guys, it could be a quick upgrade to chinos and a polo. You know your style best – pull out the best version of what you typically wear for this type of date.
Alternative dates
These usually center around things like a workout class, hike, bird-watching, or some other shared interest. Just wear what you would normally wear to something like this, but make sure you are wearing your best version (obviously pick your new workout shirt over your old one with sweat-stained underarms) and that everything is clean. Might even be worth picking up some new athleisure gear for this purpose.
I prefer activities like these for date 2 or 3, but it’s fine for a first date if you’ve been talking for a bit and have a strong shared interest.
Also, be ready just in case the date gets extended. For instance, if you do a yoga class with someone, bring a plain crewneck sweatshirt in case you want to grab a drink indoors somewhere (it can cool off quickly in AC if you’ve been sweating). It’s also a good thing to have something warm to hand your date. Women tend to get cold more easily than men, and this act will gain you some bonus points. Women love it when men think ahead.
Conclusion
Your clothes are important but not the most important thing for a date. Your confidence, personality, and ability to make her feel something (fun, excitement, curiosity, etc…) will determine your success. Knowing what to wear on a first date as a man will put you and your date at ease, demonstrating your confidence and allowing your personality to shine. This is called swagger, and it makes all the difference in the world.
Wear something you are used to wearing, be confident in your personal style, and make sure it’s the cleanest, nicest version you have. And wear good shoes.