My Cart


What To Wear On Date Night

Posted on
  • What To Wear On Date Night
  • What To Wear On Date Night
  • What To Wear On Date Night
  • What To Wear On Date Night

It’s Friday morning and you're already thinking about the night ahead because you sir have a hot date. You already have the evening fully planned out in your mind. You know where you will be enjoying a few cocktails and perhaps a light dinner to create a comforting and enjoyable experience. Who knows, maybe you're the romantic type and have some gestures planned as well.

Then it dawns on you. The one question, you should have asked yourself the moment you scheduled the date. “What am I going to wear?”

Yes, the often overlooked aspect in date night is what clothing to wear to ensure you stand out from the competition. As we previously mentioned, girls will notice how you're dressed and what shoes you are wearing. Good news for you though is we are here to help. When it comes to men’s style, it’s always best to go with classic, timeless items made from high quality materials. This will help you avoid trendy items that will have to be tossed out in a year.

Fit is another crucial aspect in men’s style. Not only will wearing clothing that fit your body properly look better on you, but it will also make you feel more comfortable. Comfort equals confidence. Confidence equals attraction. The formula is quite simple.

So what exactly should a man wear on a date? Here are some tried and true examples to set you on the right track:

The Navy Blue Blazer

Nothing in your wardrobe will be as versatile as a tailored navy blue blazer. The great thing about the navy blazer is how seamlessly it can go from a formal environment to one a little lower key. For example wearing a full navy blazer can make you a star in the boardroom. However, swapping out the matching dress pants with a pair of jeans or chinos is perfect for a dinner date, or getting flirty at a cocktail lounge on a Friday night.

A White or Light Blue Fitted Dress Shirt

Continuing on the versatility path, the dress shirt in either solid white or a light blue will be a stylish option to consider. The most important thing to remember is that the dress shirt fits you properly and does not clump up at the waist due to extra fabric. Slim fit is key when it comes to dress shirts. Also pay special attention to wear the seams rest on your shoulders along with arm length.


Black is slowly coming back into style for men but brown is still here to stay, especially as far as accessories are concerned. A great pair of brown or oxblood shoes with a complimenting watch and belt will set you apart from the crowd. Believe us when we tell you that she will notice all the details. Don’t leave anything to chance by adding funky colors. The tried and true method is the best approach on date night.

Cashmere Sweater

If the weather is a little chillier, a cashmere sweater is a great option to consider in keeping you warm while still maintaining your stylish appearance. This looks great as the most outer layer or just under a tailored blazer. Remember, when layering, the fabric should get thicker for each additional layer.

Great Fitting Jeans

Don’t hop in the skinny jeans bandwagon; you can get a great fit with a slim cut as opposed to its tighter counterpart. If you have to own two pairs of jeans only, stick with a dark blue fade as well as black. Both can be used in multiple scenarios while looking great in all instances.

There you have it. The looks described above should score you a bunch of points as they are versatile enough to wear in most climates. Remember, style is important as it is the true outward presentation of you. Let your unique characteristics show through and your girl will fall for you.

For more great style advice check out Timeless Gent.

Images used above from Mr. Porter.