There are many characteristics that define the personality of a man, the most important of them all is how he dresses up.There are many ways to dress up for women but when it comes to men, it is little difficult. There are still many ways to look presentable and feel confident on your first date. Here is a list of ten stylish ways to dress up for your first winter date.

Bomber jackets for men

There is nothing better than a cool bomber jacket on a cold winter date. It gives you a cool and casual look. In case you don’t want to look very formal, a bomber jacket and a pair of jeans are good to go.

Leather jacket

The only piece of clothing that never goes out of tending is a leather jacket. It is the safest look which can never go wrong. You can layer it up on a white t-shirt with a pair of solid jeans for a complete look.

Formal look with a suit

In some cases, you might want to keep things formal. In that case, the one and only option is to suit up. A suit can never go wrong for a formal date. All you need to remember is to get a nicely tailored fit suit that suits your personality.

10 Stylish Ways To Dress Up For Your First Winter Date For Men

Sweater and shirt

It gives you a classy and stylish look with a hint of a mature look. It is also well known a professor look. It gives a confidence of being smart and handsome. It is better to layer your sweater over a collared shirt and pair it with a pair of pants.

Cardigans with khaki

This look is much simpler to the last mentioned look. But in this case, you can wear a front open cardigan. You can layer it over a nice light colored shirt and carry this look with a pair of khaki pants. It will give you a classy look for any date.


When going for a date on a cold winter date, a blazer is a great option. The best part is that you have numerous amount of styling opportunities for a blazer. A blazer on the top of a plain t-shirt and a pair of jeans will give you a cool and stylish date night look.

Trench coat

If you are going on a date on a very cold winter night then you may carry your trench coat over any clothing. It gives a smart look and keeps you warm outside. It is good for a long drive or an outing date night. It never goes out of fashion.


It is a great option to add a muffler to your outfit on a date night. It will give you a romantic and cool look which will be perfect for a cold winter date night.


A cool hoody can never go wrong for a casual date night movie. It looks very cool and comforting in case you don’t want to go very formal.


If the weather is not that cold and you need to look stylish but also need to keep yourself warm then a cute sweatshirt paired with solid denim jeans is a great choice.

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