How to Dress for a Date

Scoring a date can be a hard task.

That’s why whenever you get the chance you should be on your top game. We have a lot of topics that cover how to dress sharp and always be on point, however, I thought that we should cover the topic of dating wear.
There are some do’s and don’t’s that should be covered and not broken.

Before starting with the outfits we should cover the basic rules that you need to follow.


Your iron should be your second best friend after your tailor. Every time you put on a wrinkled clothing you basically say ‘’I don’t care’’.
Even better, an ironed shirt will look better on your body.
So, every date you go on your clothes should be ironed, and if you don’t own an iron, then you should definitely go and get one. Preferably a nice one, to protect your clothes.

NO SNEAKERS…kind of…

Well, that’s partially true. If you are a huge sneaker head, you keep your shoes always on point, then there is no problem with going with sneakers.
However, what I’d suggest is that you go for a more dressy sneaker, something like Common Project’s Original Achilles. They just bring that extra feel of classiness to the whole outfit.


For me showing up on a date wearing a printed t-shirt is not serious. I do understand that there are some pretty sick designer t-shirts but c’mon, I know you can do better than that.
If I judge me, I’d never even show up on a date with something less than a casual button up.

Now, that we have that out of the way, let’s take at 3 foolproof styles, you can sport at any date.


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Shirt – NN07 • Chinos – Officine Generale • Shoes – Officine Generale • Belt – Mulberry •     Tie – Tom Ford • Glasses – RayBan

One thing that I totally adore is tan chinos paired with denim casual button-ups. There is nothing like this combination. It’s easy to pull off and the tie is optional, but the whole outfit is just awesome, easy to style and 100% foolproof.



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Polo – Gucci • Jeans – Dolce and Gabbana • Loafers – Gucci • Belt – Gucci •                   Cardholder – Mulberry

An absolute killer outfit for casual dates. I tend to choose brown over black in any situation, however, you’re in the safe if you decide to swap the belt, shoes, and cardholder with black.
Totally up to you, but I bet you’ll look great.


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Suit – Hugo Boss • Shirt – Tom Ford • Tie – Berluti • Shoes – Paul Smith •                              Pocket Square – Turnbull & Asser • Bracelet – Luis Morais • Socks – Sunspel

Men should dress up for dates. The obligatory blue suit should always be ready in your wardrobe. You can’t go wrong with a white shirt and brown shoes. Dress up, gentleman. There is nothing to be afraid of!


What do you think if the style above gentleman? Share your favourite outfits for going out on a date in the comments! We would love to hear from you!

– Evgeni





Evgeni Asenov

For the last 4 years I've been enthusiastic about men's style, lifestyle and fashion. Trough trial and error I've learned some things in this area and now I'm here to share with everyone who might be interested.

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