How To Dress for a First Date

You’ve got a hot date coming up. In fact, it might be the first of many with that special someone. So why not go out and enjoy each other’s company with a stylish twist? 

This guide will cover a few types of how to dress for a first date. As a man, standing out and leaving an excellent first impression will matter. You’ll learn a few ideas to dress appropriately for certain dates - whether it’s semi-formal or casual.  

Ready to make your first date one to remember? Let’s start out with the way you should dress. Here we go. 

Know Your Venue and Activity 

Here’s the thing: it is always a great idea to dress accordingly (and appropriately) for a first date. Dressing up sharp is good and all. But would you wear something you wear at a dinner party to a picnic date? 

Obviously not. So it is important to know the venue you and your date are going to. You should also consider the idea of knowing what activities are planned. For example, if you’re having a picnic date on the beach - it may be a good idea to wear something like the Heather Stripe Windjammer Hybrid shorts offered by Vintage 1946. 

We should also add that you want to dress appropriately for the season. Obviously shorts won’t cut it if it’s winter time and it’s below freezing. Plus, it might be the biggest fashion faux pas you commit in the history of first dates. 

Also, be mindful of whether or not the date is indoors or outdoors. In the case of the latter, you’ll want to plan accordingly for any weather-appropriate clothing. Pay close attention to the weather conditions in the days leading up to the date. 

This way, you’ll be able to make on-the-fly style changes when necessary. If one forecast calls for sun but changes in a couple of days to possible rain, it may be a good idea to have some alternative clothes on standby like a raincoat. 

Also, a Plan B for the date should also be considered as well especially if it was something you two planned on doing outdoors. 

Keep It To Your Personal Style 

Needless to say, we’re not suggesting you dress something that’s outside of your preferred style. Keep it to your personal tastes as you like. At the same time, you should be able to abide by the rules of what’s venue and seasonably appropriate. 

If you like the timeless classic style in the same vein as JFK and Paul Newman, pay attention to what they wear in terms of what’s appropriate for the venue and the season. There are plenty of pictures of them online and on social media (including Instagram accounts dedicated to men’s style).  

There’s nothing wrong with wearing a button-down with a pair of Vintage 1946’s Vintage Stretch Twill if your first date is a cup of coffee and some conversation. It’s venue appropriate and if it’s not too hot of a day outside, it can be seasonably appropriate too. 

Your Body Type Matters When It Comes To Fit 

One of the biggest fashion mistakes any man can make is wearing something that is ill-fitted. It needs to be something that fits your body type. Men come in different shapes and sizes - so it’s always a good idea to find clothes that fit you perfectly. 

Nothing too tight or baggy. It also might help if you get clothes altered and tailored to fit you, if possible because wearing something that is tailored to your body type will certainly fit you perfectly. It’s way better than playing the guessing game whenever you’re shopping for clothes. 

Make Grooming a Priority 

Sure, it’s the clothes that make the man. But it’s not the only thing that matters. If you want to look your best beyond what you’re wearing, groom accordingly. 

This includes making sure your nails are clean and trimmed, your hair (both on your head and face) is trimmed neatly, and you’re looking your absolute best. Couple this with the clothes that fit you best and you’re off to the races (not the Kentucky Derby or Indy 500…unless that’s actually the date). 


By following these tips, you will certainly rock the style game on your first date. Whether it goes well or not, you will certainly have this guide as your go-to whenever you need to answer the “what do I wear?” question. If you need to check out what Vintage 1946 has for excellent clothes to wear on a first date, feel free to visit our site.