7 Best First Date Casual Outfit Ideas for Men

7 Best Casual Outfits for Men to Wear on their first Date

The first date has always been the first step toward finding true love. When you go on a date with someone you want them to see the best version of yourself. You want them to know how you are better than the rest.

We all know the saying which goes like,” the First Impression is the last impression” and it is so true. We don’t get a second chance to make our first impression. The first date always gives you the chance to portray to your partner how interesting you are.

The saying that,” looks makes a man” goes very well when it comes to first dates. You have to have a good selection of clothes so that you can make a long-lasting impression as it’s your first date.

When we go on a first date the very first goal is to get another date. So for that, you should have a great outfit, nice and good conversations, and cute moments. But this all starts with a good outfit. So to help you with all your doubts about outfits to wear on your first date we are here. 

But before starting off with the outfits, you must know that whatever you wear, wear according to the date, time, activity, and season. While being comfortable it is necessary to wear clothes according to the occasion. 

This means if you are going on a day date you should have a different set of clothes and if you are going on a night date then you should surely change the outfit.

If you are going on a day date then a pair of smart jeans with a casual polo t-shirt or anything printed would be enough to go with. A comfortable pair of shoes would undoubtedly be best for your look.

But if you are going on a night date then there have to be some changes in your outfit. If you are going to a fancy restaurant then you should definitely go for a shirt and a well-fitting suit along with a fine pair of formal shoes to uplift your attire.

So now we go, here we have listed a set of casual wear for men that are undoubtedly date-worthy. 



Many people think that polo t-shirts are meant for athletic purposes only. But let me tell you, they are no more confined to gyms and playing fields only. 

The best choice is the polo t-shirts when you are thinking about having a formal meeting with your partner. Polo tees are no more just sports favorites, they are more than just sportswear now.

Polo tees are one of those outfits for men that fits your everyday look. If you are going for a day date then you can surely go for these.

A little style tip, if you want to keep it simple yet stylish then you can just tuck them in any straight pair of pants along with formal shoes.

And if you want to go more casual then, you can just replace the pants with ankle-length jeans and add a pair of loafers and that’s it, you are all set for the date. 



Selecting shirts can sometimes be a headache of course but one thing no one can deny is that white shirts are one of the best choices for menswear. These can be both formal wear and casual too. 

White shirts are one of the classic items that can never go off trend. They are always in trend and of course a staple outfit item for men.

White shirts are not just for boardrooms, they can be extremely fashionable and casual when carried out correctly.

A little style tip, if you want to make it look casual, then just go with a white shirt and a pair of jeans. Distressed not the ripped one to be precise, pair them with sneakers and that’s all.

Layering can always help when it comes to shirts, for these, just pair this classic with another classic, denim jacket and you are all set to step out.



Denim has always been one of the men’s favorites. Every man has a pair of denim jackets or shirts or just denim jeans, at least one of these are always there in their wardrobe. And there is no way that any man can deny it.

Denims are so versatile that they go with everything that you want to pair them with. It always gives an option for experimenting and creating your own style statement.

A little style tip, starting off with denim shirts, pair them with chinos and a pair of your favorite white sneakers.

Denim jeans are one of those you can rely on whenever you can think of anything else. Style your denim jeans with a t-shirt and a pair of sneakers and you are all set to go.

As layering is one of the most fashionable ideas for everyone, you can just layer your plain t-shirt with a solid denim jacket and you are good to go.



T-shirts can be the easiest choice when we are looking for comfort and style at the same time. 

You may think that why t-shirts because many of us believe that t-shirts are not the type of casuals that can be worn as an outfit for dates. 

But you should know that nowadays t-shirts have gained a lot of respect and reputation when it comes to casual and comfortable clothing. T-shirts are easiest to style, they are simple and yet can give you the best looks.

For an effortless look, you just need to have well-fitted t-shirts and that’s it.

A little style tip, the easiest of all can be a slim fit t-shirt paired with denim and a pair of casual sneakers.

Jackets go best with t-shirts, pair your favorite t-shirt with a perfect color contrasted jacket and a pair of sneakers.

And if you want to make it extremely casual then just go for a printed tee and a pair of denim and sneakers and you are good to go.

Chinos also go well with t-shirts. So if you own a chino then you can for sure pair them with your t-shirts. Also, accessorize this outfit with just a watch for a sleek look.



As I have said earlier, layering can never disappoint you and jackets are those who help you believe that. Most men go for the basic dressing but you should know that a jacket can be as basic as your t-shirts and denim jeans. 

Also, layering helps you to make a statement that you just don’t go for something which comes first in front of your eyes. You look and pair your outfit with the jacket. Well, that’s something of course impressive.

There are a lot of jackets that you can go for, but make sure that it’s weather friendly. You don’t want to be all soaked up in sweat on your first date, or just feel cold all the entire time.

A little style tip, if you are going with suede jackets then just pair them with any color contrasted t-shirts and any pair of comfortable sneakers, yes, it’s that easy.

Sweaters and long coats are winter favorites. Pair them with t-shirts, skinny jeans and a pair of boots.

If you don’t want to wear overcoats or sweaters then you can just go for cardigans, wear them over any loose t-shirts and good and casual sneakers. 



If you wear prints according to the occasion then you can be disappointed. Because there is no way prints would ever turn you down.

If you know how to pair the printed shirts then you are always safe. You just need to know the correct combinations and that’s all. No matter what you are wearing, patterns always stand out from others.

When talking about printed outfits, the first location that comes to mind is beaches. So if you are thinking of having a date at the beach then you can surely go for printed ones. Either you can just go with a printed t-shirt and a pair of shorts or you can just layer your plain t-shirt with a printed shirt to enhance your look. When going to a beach, never forget your shades.

To keep it simple just tuck in your printed t-shirt. Be it any bottom wear. But remember never wear denim over printed shirts. Wear chino pants and a pair of nice loafers and you are all set for your date.



Semi-casuals are always best for dates. They give a dapper look that no one can ignore. Suits are one of the favorite outfits in which women want men to see them. 

Suits help you simply look best and also helps you to bring out the inspiring you. Just find a well-fitted suit and you need nothing more to slay.

Blazers are generally seen as more formal outfits, but little we know that we can really incorporate them into a real casual outfit best for dates. The real deal with blazers is selecting the correct color of the blazer to suit the occasion. 

You can just wear a blazer over a t-shirt to give the casual look that you want to have.

Always use blazers to layer your basic outfit to make it look casual.

Always wear contrasting colors, neither too vivid nor too light.

You can go for both loafers and sneakers if this is your outfit.

So these were the 7 casual outfit ideas for men for their first date. Pick the correct outfit for you and make your first date a remarkable one.

But other than the outfit there are many other things that are to be taken care of when you are going on a date. Here are some of the do’s that you cannot avoid if it’s your first date.

  1.  The first and foremost thing is to have everything planned. You have to have everything planned. Never ask your date about what we are going to do. You should have everything planned beforehand. If it’s the dinner date that you are going to do after that, are you gonna drop here home you are just going for a walk after dinner. Just have a plan.
  2. The second most important thing is being punctual, if the time set for the date is 8, then be there beforehand. Or if you are going to pick them up from their place then be there on time. 
  3. Thirdly, say no to your cell phone. We all have the habit of using phones all the time, so keep it away the entire time. You know they say “out of sight out of mind”. Just keep your phone away from you to avoid the temptation of using it.
  4. And the most important thing that you should do is show interest in the other person. Have questions for them, but don’t ask all of them at the same time. Take your time and also give them the time to answer.


As first dates are important in one’s life, so why not make a remarkable one. Good outfits make you stand out from the crowd. That is why we gave you the guide to the 7 best casual outfits ideas for men for their first date. Just go get the one that suits you the best and find yourself a match. 

Looking good is very difficult at times. So if you are also this problem right, just give this piece a good read and you will be able to find yourself a good casual outfit idea for your first date.

Just remember that what makes you comfortable makes you look good too. So find yourself something that you are comfortable in and you are all set.

Other than this if you are also into casual wear then do check Chillme for getting the best casual wear for you.


What not to wear on the first date?

Avoid too many accessories, just keep it simple and sober.

Other than outfit what is important?

Accessories like watches and shoes play an important role. Cologne(perfume) is also very important.

Is wearing jeans on the first date okay?

Jeans are always the first choice of many, so if you want and you feel comfortable in them then you can for sure go for it.

What to talk about on first dates?

Just start off with knowing the other person, their likes and dislikes. This may sound old-fashioned, but it works and it makes the other person feel that you are interested in them.

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