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What to Wear on a First Date

What to wear on a first date

Hint: It's not sweatpants.


Penned by: The Dapper Boi

It’s an exciting time. Spring is in the air, COVID is seemingly winding down (we hope), and Lady Gaga’s French bulldogs were returned unharmed. It’s also a time where going on a date in public won’t get you as many dirty looks, although coughing is still a big no-no.

The only problem? After all the social distancing, quarantining, and binging of true crime docs, most of us are a little rusty on the social front. Even if you aren’t, knowing what to say, what to do, and what to wear on a first date can still be a nerve-wracking endeavor. 

The stress of choosing the right outfit, especially after having spent the last year in "comfy clothes," is to be expected. You want to make a good first impression, and clothing is a strong starting place. Plus, with so many fashion “rules” floating around, it can be hard to distinguish what’s hot from what’s not. But, it doesn’t have to be. If you’re single and ready to mingle (last rhyme, we swear), the following tried-and-true tips are for you!

Image of person with way too many clothes. Dapperboi.com

1. Wear Something That Makes You Feel Most Like… You

The simple answer to the “what should I wear” question is: whatever you want, of course! At the end of the day, it’s all about choosing something that makes you feel comfortable and confident in your own skin. As cliché as it sounds, relaxing and being yourself is key to a successful date.

2. Don’t Be Afraid to Be Bold

Wear what works with the look you want to achieve, whether that means bright colors, or a fun hat. Wearing genderless clothing in itself is daring and rebellious. Heck, even shopping for gender-neutral clothing is a bold act, although not for long thanks to a certain clothing company. Ahem, ‘nough said.

3. Be Reasonable With Your Choices

But, you just told us to be bold. You’re right, we did, and you can. But just know… showing up to a first date in nothing but a pair of parachute pants and a glossy gold vest probably won’t earn you any bonus points. (Unless you’re MC Hammer, but even then, it’s a stretch.) Those of us who understand that the 90’s were a time of questionable fashion choices might be better off keeping it simple.

4. Don’t Dress for the Wrong Type of Date

It really comes down to the setting and person who will be sitting across from you. Wearing a suit and wingtip shoes for a lovely walk on the beach isn’t going to be that lovely. Just as wearing shorts and a t-shirt to the opera wouldn’t be the right choice. Who goes to the opera on a first date, anyway?

Image of individual in tuxedo at party. Dapperboi.com

5. Keep It Comfy 

Keeping it comfy can help you look more inviting. It also prevents you from enduring the misery of wearing an outfit where you constantly feel the need to “suck it in.” Again, keep it reasonable. Again, sweatpants are a no-go when it comes to first impressions. Yes, even during the COVID era.

6. Have Fun With It

Work your hair, nails, and accessories as you see fit. There really aren’t many rules when it comes to accessorizing, especially these days and in the non-binary space. If you want neon green nails, go for it! A mohawk? Time to hit up your barber and watch SLC Punk! Just make sure whatever you do matches your outfit.

7. Most Importantly, Don’t Stress Out Too Much

Few things in life can make your palms sweat more than a first date. And like I said, picking out an outfit can be a daunting task. But, it’s just a date. Life will go on if it isn’t a good fit (no pun intended). Some dating experts even believe it’s what you wear on the next few dates that are most important. For instance, dressing down can be a sign you’re becoming more comfortable with this new person. And as we’ve learned, comfort is key.

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