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It's a Guy Thing

What to Wear to a First Date

So the great thing about first dates is the fact that it could be the start of something. Now, whether that something is “the end” or “prepping for date number two” depends totally on your first impression.

by Bold Support

February 03, 2017

What to wear to a first date


So the great thing about first dates is the fact that it could be the start of something. Now, whether that something is “the end” or “prepping for date number two” depends totally on your first impression. Forget all the romantic poems you had to compose to get her out on this first date; if you show up looking like she made the wrong choice, then chances are that you won't be making it to date two. On the other hand, you could sport a really good look and who knows, it might be your lucky day.

Chances are that you have no idea what to wear to your first date. While we cannot choose your outfit for you, this article is poised to provide some answers and narrow your options down to what fits. So let’s get right into it.


Make Sure You're Groomed!

Before we get to the part where we recommend you outfit ideas, make sure you are well groomed for the date. This implies that your hair, nails, teeth and body has to be clean. If you are sporting a beard, keep it tidied up. Remember, you are trying to make a first impression and quite frankly, it could be the last impression, so make sure to accomplish the basics here.

Extra Tip: Keep the cologne light –nothing too heavy. It’s not like the cologne company is paying you to advertise their products.


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After your grooming, the outfit follows. Jackets, aka your most outer layer, is a great place to start. No matter what you wear underneath, make sure to add an appropriate jacket on top. Going for an elegant dinner? Wear a pea coat. Grabbing a burger? Try a t-shirt with a bomber over top. Jackets also have the added benefit of giving you a chance to be chivalrous when she gets cold at any point during your date. 

Extra Tip: For casual dates, you could try an understated leather or a bomber jacket. Check out our article on bomber jackets for great tips on how to rock the bomber jacket. For a formal date, a wool pea coat just about does the trick.

Mens outerwear, first date outfit ideas, mens fashion

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These are important. You know those beautiful shirts with the floral designs your mum got you for Christmas? They don’t work here. Your first date is not the time to be seen rocking your most outlandish outfit. Keep your tops simple, classy and understated. Now, we’re not saying you should look like 007 but it beats looking like a walking carrot with that orange and neon green attire.

Extra Tip: Try a blue oxford shirt with a dark slim-fit denim jean.


what to wear to a first date

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Next to your nails (for obvious reasons) and shoes, trousers are another thing ladies will definitely notice. Just like the tops, keep your trousers simple, dark and slim fitting. Make sure that your pants are stain and odor free.


trousers, what to wear to a date



Women find shoes to be a really big deal. Quite frankly, no one knows why women place so much value in shoes but it is what it is. Getting your shoe choices wrong simply means your date just started off on a wrong foot…literally!

Extra tip: Keep your choice of footwear classic. Try loafers, canvas trainers, desert boots and brogue boots.



Sporting a simple accessory ensemble gives room for improvement in your subsequent dates. Instead of flashy, go for timeless, simple and elegant. Opt in for a clean timepiece, bracelet, and maybe even a few rings.


Daniel Wellington, Accessories, Date Night

Daniel Wellington ($279)

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