What to wear on a first date?

A first date can be nerve-wracking by itself. So, adding an extra-dose of confusion regarding what to wear can certainly make it much worse. We may not have a solution for all your concerns, but we can definitely help you choose the correct outfit to boost your confidence.

Looking great on a first date

Looking good on a first date is crucial in order to leave a good first impression. And that’s why we recommend taking your time to plan a spot-on look and avoid throwing any random clothes on only a few minutes before stepping out the door.


What to take into consideration

Dates in general can be a little stressful and anxious, especially the first ones. So, you have to try to make yourself feel comfortable in every possible way. And that, my friend, is why comfort should be one of the main priorities when it comes to choosing your look.


Now, we don’t mean sweatpants and t-shirts you often wear at the gym. But, actually, garments that make you feel at ease, that bring up your strengths and boost that confidence right up. A first date is the type of occasion where you actually want to stay in your comfort zone by picking up garments that both highlight your style and your personality.


Aside from a comfortable, self-assuring outfit, you also want to consider the location you are going to and the time of the day. Clearly, it’s not the same going for a walk in the park than having dinner at a fancy restaurant. So, before you think about what to wear, you need to establish when and where you are going to. But enough premises, let’s get real!


DOs & DONT’s

Unless you’re attending a fancy event, first dates tend to be a casual occasion. Hence, your outfit should be relaxed too. By all means, casual does not mean unkempt. Any sporty-clothing should be out of the question when thinking about dates. That is hoodies, sweatpants, gym t-shirts, running sneakers…


If that’s actually your style and you don’t know how to substitute these garments for more accurate alternatives, here are a few ideas. Instead of a hoodie, you can opt for a bomber jacket, for example. You can match it with a button down shirt or polo shirt for that classy touch, and complete the look with a good pair of black jeans to maintain the casual vibe. To top off the look you can choose a pair of lace up boots. On the other hand, there are still other alternatives you can check out that are as comfy as sweatpants, like cotton chinos, for example.

There’s too casual and there’s too formal as well. When going on a first date, you don’t want to overdress and look like a corporate businessman. You can still have that smart casual look, just avoid using a tie and the same blazer you would wear to work. Instead, you can opt for a more relaxed blazer or a Harrington jacket.


For the perfect dapper look, you can combine a neutral pair of dress pants, along with a basic shirt, a stylish sweater and a pair of Chelsea boots. If it’s too cold, then you can add a smart casual jacket or a modern coat. This could be a great winter outfit for a nighttime date.

Stylish man on first date

Let’s do a few more examples. A plain t-shirt can be too basic for a first date, yet combined with the right elements it can go a long way. You can wear it with a matching pair of chinos, along with smart-look sneakers and a denim jacket to complete the look. It’s laid back, but still refined.


Another option is to combine a pair of boot-cut jeans with a plain t-shirt, while taking it to the next level with an unbuttoned Oxford shirt. Major styling tip: roll up your sleeves up to your elbows for an ultimate summer time vibe.


As you can see, it’s all about finding the perfect balance between casual and stylish. To sum up, you should mix casual, daily garments with more classy, elegant items. So, you could totally go for a basic graphic t-shirt or a classic pair of jeans if you’d like to, just make sure to step up the game by combining them with a few more sophisticated elements too.



We’ve given you several ideas on how to put up a look for a casual first date. Now, it’s time to make this outfit your own. What do we mean by that? Well, you want to add details that bring up your personality and the way to do so is by accessorizing. As we always say, style is in the details.


You can accessorize by wearing a statement watch, but also by adding a minimalist ring on one hand or a subtle bracelet. If it’s a daytime date, a pair of fashionable, modern sunglasses will definitely do the trick.

A few more things. As we said at the beginning, first dates are all about leaving a good first impression. Therefore, make sure you look on-point before you leave your house, from head to toes.


So, verify if your shoes or sneakers are clean and polished; check if your shirt is properly buttoned (leave no more than three buttons free); make sure to spread some cologne; and corroborate if your beard looks flawless. In fact, in this article you’ll discover 8 tips for how to keep beard hairs from sticking out.


All these things will certainly make you feel confident and optimistic, as well as they will make your date understand you actually put an effort for them. Remember to stay tuned with us for further styling tips and the latest fashion trends for men.