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What to Wear On a First Date

What to Wear On a First Date


Some first dates (finally) get scheduled after hours of texting on an app while others are planned shortly after a brief meet-up. 

Regardless of how you get to the first date, picking what to wear for it is tricky. It’s finding the intersection of making a memorable first impression, showing that you put in the effort, and being chill enough to stay comfortable. 

It’s trying to show the guy that you’re meeting the best version of yourself. 

The clothing that you wear will influence your mindset, as well as your perception. Whether you’re bold with a strong sense of style or you’re indifferent to clothes and fashion, first date dressing anxiety comes for us all. 

Robert Ridge, a psychology professor at Brigham Young University, explains,

“There definitely can be a connection between how people dress and how they feel. The more you like your appearance, the more confident you can be.”

Here is a collection of styling suggestions to help you look great and feel confident for the first date. 

Neutral or Dark Colors

For the first official hang, don’t dress in clothes that appear forced or look like a costume. Let Klaus, from Umbrella Academy, be Klaus. 

Stay clear of covering yourself in excessive patterns and mind-blowing colors. Instead opt for neutral or dark colors that will showcase more of you and less of what you’re wearing. Dressing in monochrome is a smart way to show that you dabble in styling magic and use your powers for good. 

Monochrome outfit for gay dating

If it Fits, Wear It

From your shoes to your shirt, the fit is everything. 

Even if you're swol, skintight clothes are never flattering; conversely baggy clothes can create awkward-looking proportions. You never want to look like you’re wearing someone else's clothing. Regardless of your body type, wearing clothes that fit you well is always the right size. 

Choosing the right fit for the first dateThe Bonobos Fit Guide has copious information, photos, and video on how men's clothing should fit. 

Find a Layer

Add a layer to what you’re wearing, even if it’s a simple one. Due to COVID restrictions, we’re meeting up outside more often so it’s smart to have the clothing layers. Esquire’s book on men’s styling, Dress Code provides sound layering advice. 

“Throw a button-down shirt, unbuttoned over a T-shirt, for instance. You can also try the same move with a cardigan, or even, during the colder months, a light bomber or Harrington jacket.”

Also, you can never go wrong with a leather jacket. 

Layering gives more visual interest to your lewk and shows you thoughtfully selected what to wear.

Layering in men's clothes

It’s Not a Job 

Meeting up for a date is supposed to be a good time. Nobody wants to feel like they’re at work or in a job interview. 

Wearing formal business clothes to a date sends the wrong message about you and can make you appear stuffy. What’s worse, it can shift the vibe too. What you wear should reflect the polished chill side of your personality. 

If your date is scheduled directly after work, bring clothes to change into. You’ll feel fresh and be more comfortable. Comfort will lead to confidence. 


While shoes are practical items, they also give insight into the person wearing them. Think about what your shoes will say about you. 

Trainers are obviously cool, especially fresh white ones. Wearing a cap-toe or derby shoe can dress up a casual look. A Chelsea boot or a Red Wing is an excellent choice. Boots have a distinct personality and give the person wearing them presence. 

Whatever shoes you choose, make sure they’re cleaned up and tidy before you step out of the house. 

Shoes to wear on the first date

Add One Interesting Accessory

Adding an interesting accessory will personalize what you're wearing. It imbues personality into your outfit and conveys a bit of who you are. The point of a date is to share your personality.

Sliding on your favorite watch or a vintage ring always looks good. A gold chain across the chest - I love it. 

But know when to stop. Less is more when it comes to accessories.

Accessories for men

Wear Your Best Underwear

For a first date, always put on your best underwear. There is self sorcery to wearing your favorite underwear. It boosts your tenacity and reminds you how hot you are, similar to getting a great haircut. That is exactly the mojo that you want heading into a first date.

Also, like a good Boy Scout, it’s best to always be prepared.  

Best underwear for gay date


Here is a short list of recommendations to avoid wearing on the first date.  

No Ties

Unless your first date is to a legitimate event, skip the tie to keep formality low and comfort high. 

Open Toe Shoes

Exposed man feet are not for first dates. Save the Tevas and Birkenstocks for wearing to brunch the morning after or a dog walk down the road. 


Keep it light and unobtrusive. In the words of Jonathan Van Ness, “Spray, delay, and walk away.”

Beware New Shoes

Observe caution if buying new shoes for the first date. Shoes fresh out of the box take time to break in and your introduction to a guy isn’t the best place to start. 

Hoodies & Sweats

Everyone likes to feel special, so show that you put some effort into the first date by wearing more than your Twitch and chill clothes. 

Personal style is unique to you, just like first date experiences. The perfect outfit is relative to how you see yourself and move through the world. 

The best fashion advice is “if you feel good, you look good”. When that happens, all the rest follows. 


Matt McFall for KeYou