What To Wear On A First Date For Guys


Going on a date with someone requires you to be at your best. This is because first impression matters a lot. If you want more dates with her to happen then you simply have to be on top of your game. This starts with your dressing. The initial assessment of you by your date will come from your physical appearance. You may be the sweetest guy on the planet but if you turn up on a first date shabbily dressed, the chances you will be going on another date with her are slim to none.

That said, you don’t have to break the bank or spend all your savings on fancy clothes to impress your date. It takes a little bit of fashion sense to pull off that sharp look that will earn you a second date. This article will provide some tips on what to wear on a first date for guys. So next time you have a date with your crush, you will turn up sharply dressed. A date atmosphere is usually relaxed so often than not, your dressing should match this mood.

What To Wear To Wear On A First Date Guys

Finally, you have asked her out on a date and she has agreed. You are excited as you should be but really, there is a lot left to do for you to woo her. This underscores the importance of first dinner dates. Your overall performance at your first dinner date will determine if you will get another with her. A very good way to ensure you do not get another date with her is to show up shabbily dressed. Your appearance at your first dinner date will go a long way in influencing her decision.

Look sharp and be sure she has some bias for you already. Even if you don’t impress her with your conversation during the date, your sharp look may give you a second bite at the cherry. Now I don’t think I have to stress the importance of dressing smartly to your first date. Just in case, here are a few reasons why your appearance to a first date matters a lot.

Why You Should Look Fly On Your First Date As A Guy

Your looks are important.

Same way men are naturally drawn to physically attractive women, women are also drawn to attractive men. You will be doing yourself more good than harm by turning up sharply dressed to a first date. Correctly worn clothing can help improve your looks by accentuating your positive masculine features and toning down on the less flattering ones.

Your date is sizing you up

First dates provide a platform for both parties to get to know each other on a deeper level. You are both studying each other, picking up signals about compatibility, personalities, and long-term potential. Not all these clues will come from conversation, some will come from non-verbal behavior as well. So it is important that your dressing sends the right signals, show respect, and also reveals your personality.

Shows Respect

Considering your date will most definitely be putting a lot of effort into her looks to the date, it will only be appropriate for you to reciprocate by dressing well too. This is simply being respectful.

Puts you in the right state of mind

When you are well dressed and confident about your appearance, your mind is relaxed. That way you will be focused on the task at hand which is getting to know your date better. On the other hand, dressing badly will make you feel uneasy and unable to focus. This will end up costing you a second date.

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Shows your social skills

The way you dress is the way you will be addressed. When you are sharply dressed, it is most likely people will warm up to you easily which makes socializing easier. For your date, this is important as she will be thinking of how easily you will bond with her friends and family later if you both end up dating. You don’t want her to have the impression that you have bad social skills do you?

Your healthy masculine features are highlighted.

It is important that you leave a good impression of yourself on your date. This does not have to be intellectually alone, you also have to impress her with your physicality. The right clothing can aid your cause by accentuating your healthy physical features. Masculine features such as square lines in the face, broad shoulders, muscular chest, smaller stomach than upper torso etc. can be highlighted by clothing such as a sports jacket. To you, these features may not matter but to a woman, they do as they are indicators of a healthy level of testosterone.

Helps to keep attention on your face

The right clothing will help to keep your date’s attention firmly on your face. Your dressing should not be overly excessive as this can be counterproductive. Steer clear of flashy accessories or clothing that attract too much attention to itself. Those types of clothing and accessories are not appropriate for a first date.

So now that we have discussed the importance of smart dressing to a first date, here are some style options for you to consider.

What To Wear On A Casual First Date Guys

what to wear on a first date

Casual dates, especially outdoor ones, require you to wear a relaxed outfit. This doesn’t mean you don’t have to put effort into styling your outfit. Stay away from plain blue jeans, work clothes, sweatpants or athletic pants (unless it’s a jogging date). Consider the following.

Dark Denim

Dark straight-leg jeans are universally flattering and will pair well with a variety of shirt. Also, the darker wash will make you appear taller.

Collared shirt

For a first date, it is a must you put on a collared shirt. The exception will be when you both are off on a serious sporting adventure. In this case, wear a button-up shirt or polo.

Leather Belt

Your shirt must be tucked in for your first date unless you are headed to an ocean beach. So, be sure to add a leather belt to your jeans for a sharp look.


Go for shoes that match the color of your belt. A dressier shoe is the best option when you are in doubt. A Chelsea boot or a derby shoe will work with dark denim while a canvas sneaker is acceptable for a more laid-back date. You have to make sure your sneakers are clean though.


You have to be minimal on accessories for your first date. Your accessories shouldn’t be competing with you for your date’s attention. So keep it simple. You can stick to a classic watch or cuff.

What To Wear On A First Dinner Date Guys

For a first dinner date or an evening event in an urban setting, a jacket is often required. Jackets are known to help men look more masculine and authoritative. They are also easy to remove if it gets too hot or if the situation is more casual than you anticipated. Read more on what to wear on a first dinner date below.

Dress Shirt

For dinner dates, dress shirts are a perfect choice. Polos and T-shirts are not allowed as you are required to pay more attention to detail when dressing up for the evening. A solid dress shirt or a plaid shirt will serve you perfectly for the evening.

Dark Denim/Chinos

Dark denim that is well fitted will pair well with any dress shirt. It will also complement your body. For non-lovers of denim, chinos also work fine for dinner dates. Navy or blue chinos should generally do the trick.

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Blazer adds a touch of masculinity and sense of style to your look. It is important that you pay attention to pattern variation. Play it safe by opting for just one pattern (either blazer or shirt) and two solids. If you are adept at combing patterns, it is preferable to pick your blazer and shirt as your patterned items.


The more formal your outfit, the more formal your shoes should be. You have to ensure that your shoes are clean, functional, stylish. Loafers, brown leather shoes or wingtip brogues all will work with your outfit. For the jeans option, a trendy pair of sneakers can also work.


For dinner date, your accessories can help bring out your personality. Skinny ties, printed silk ties, pocket square, and pocket flowers can be combined with your outfit to your first dinner date to achieve the sharp look you desire.

What To Wear On A First Date For Drinks

Going on a drink date with your crush requires you to dress casual. Usually, drink dates are during the day so you can employ a minimalist look. This does not mean your outfit should be plain or simple. You can go for a jacket, and a gorgeous white T-shirt paired with simple khaki pants. Compliment your dressing with a simple and stylish wristwatch. A pair of white sneakers will match your outfit perfectly.

What To Wear On A First Date To The Movies

For a first date to the movies as a guy, opt for something dressy while still being casual. Movie dates lean more on the casual side but that doesn’t mean you should not dress well for the occasion. A long-sleeve button-down shirt with jeans will suffice for a movie date. The jeans should be fitted and dark, not baggy or acid-washed. While a long-sleeved button-down shirt is preferable, a fairly new, soft, and fitted T-shirt will work just fine too.

What To Wear On A First Date Summer

Summer is a time of the year that presents a different challenge when dressing up for a first date. Your usual go-to outfits must be discarded as you now have the hot weather to contend with. Your priority should be staying cool in the heat. So, you have to keep your outfit simple. As a guy, you can go with a plain high-quality T-shirt, paired with jeans or chinos.

However, if you still want to layer up in summer then the following options will suit you. Blazers made from super-thin materials such as linen can give you a cool contrast when layered over a T-shirt. You can also go for jersey polos. Jersey polos feel like T-shirts as they are made of soft material but have more details like collars and buttons.

What To Wear On A First Date Winter

what to wear on a first date in winter
first date winter

The winter cold makes layering up a must when going for a first date. Here are some ideas on what to wear to a winter date for guys. Uptight looking suits should be avoided as these are reserved for operas, theatre or the most prestigious restaurant in town. If your date location falls under any of these categories then, suiting up is a perfect choice.

You should generally look to keep things smart and casual. A simple light shirt, preferably a plain T-shirt under a sweater is acceptable. Pair this with Jeans. Complete your look with a suitable coat. Smart jackets are a perfect choice or knee-length wool coats. These will help keep you warm and at the same time give you a sense of sophistication without looking pretentious.

Men’s Night Date Outfit

For night dates, you can go for a white cotton shirt, wool trousers/dark denim and leather belt combo. You can add an extra layer by throwing on a jacket.


The challenge of what to wear on a first date is one that a lot of guys have to contend with. The added pressure of making the most of the first date to impress their crush may make this worse. You don’t have to sweat too much over this or break the bank as you must have realized by now if you read this piece. If not, now is the time for you to go over and read the piece fully to digest the knowledge shared.