The Do’s and Don’ts of First Date Fashion | Avoiding Common Mistakes

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Want to be fashionable on a first date? Of course you do! Unless you are too “cool” to care about first impressions—which is not a good look, speaking of fashion—then you’ll want to find out what you should and should absolutely under no circumstances wear on a first date.

We aren’t saying you have to hit up Saks Fifth Avenue and style yourself from head to toe in couture. Although, if you can do that, by all means, go right ahead!

No, this is more of a simple, mostly common sense list of common fashion mistakes we sometimes make in the anxiety and anticipation of a first date with someone you’re into.

Ladies, if you are having a pre-date wardrobe meltdown and your room looks like a cyclone blew through and tossed every piece of clothing you have around, we have been there. 

We can’t really picture men having a panic attack over what to wear, and is that sexist? Probably! But maybe they should put more thought into how they appear on a first date—just food for thought, fellas.

Your first date look should say, “I’m a well-adjusted, dateable human being,” and you should not be stressing out over whether mixing polka dots and stripe patterns is a little too much. 

Your choice of wardrobe doesn’t have to be so complicated, so let’s dissect some of the most obvious (and not-so-obvious) style no-nos. Here are the dos and don’ts of first-date fashion so you can avoid common mistakes! 


pink tank top, blue jeans and gold hoop earrings

Do: Wear Something Comfortable

Comfort is king, or queen, or whatever regal figure you choose. If you spend the entire first date adjusting your new skin-tight body con bandage dress that feels like a scuba suit or silently begging the heavens for the sweet release of death because your new shoes are staging a mutiny against your poor feet, you’re not doing it right! 

Being comfy doesn’t mean showing up in your fave (read: worn through and with some holes) sweatpants, though. Pick a middle ground! Style doesn’t have to hurt or be uncomfortable—you want to look nice but not physically suffer, and not having to perform acrobatics to sit down is kinda important. But don’t be too comfortable and show up in your well-worn loungewear, okay? Okay.


yellow sweatshirt and pink athletic shorts

Don’t: Turn Up in a ‘Lucky’ Clothing Item from High School

This one’s for the men—we get it; you made the game-winning shot in the state championship b-ball game while wearing whatever your “lucky” piece of apparel is, be it a tee shirt, hoodie, or underwear. But if your lucky charm clothes have seen better decades and are holding on by a thread, it’s time to let them go. 

This applies to any clothing item that’s been part of your life longer than smartphones. Nostalgia is a lovely sentiment, but not at the cost of looking like you’ve dug up the time capsule you buried in your backyard to put together your outfit.


pink wrap dress, white button down, khaki slacks

Do: Dress Appropriately for the Venue

Nothing says you put zero thought into it or “I didn’t even bother to Google,” like showing up to a fancy-ish restaurant dressed like you’re headed to a sporting event or wearing a three-piece suit to a casual spot. 

A quick venue check to ensure your outfit matches the venue’s vibe will save you the embarrassment of sticking out like a sore, overdressed (or underdressed) thumb.


tie-dye shirt, cow print purse, pineapple socks

Don’t: Go Full Experimental Mode

First dates are not the time to bust out that avant-garde attire that could double as a modern art installation. Unless you’re both into that, which, by all means, carry on. 

Just sticking to the classic “I’m a grownup who knows how to dress themselves” is the safest and best bet. You can debut any fashion-forward statements for after they’ve already seen you and are sticking around!


blue jeans and long sleeve shirt

Do: Pay Attention to Details

Small details really do matter! Wrinkled shirts declare, “I was too lazy to iron this,” and grubby shoes say, “I couldn’t care less.” Taking the time to make sure your clothes are clean, ironed, and not missing any important buttons will dramatically improve your first impression. 

It’s letting your date know you’re capable of adulting without actually having to say it out loud.


perfume bottle

Don’t: Douse Yourself in Perfume or Cologne

The goal is to attract your date, not asphyxiate them. If your scent arrives five minutes before you do and lingers two days after you’ve left, you are overdoing it. 

Fragrance should invite someone in, not send them running for fresh air or ask the maître d if there is a gas mask they can borrow. Spritz yourself sparingly—you want a “hint of mystery,” not “chemical warfare.”


low-cut blouse, jean skirt and gold necklace

Do: Show Your Personality

Your outfit is a spokesperson for your personality, so let it say something about you. If you’re laid-back, your clothes can reflect that. If you’re more polished, that’s fine, too. Just don’t try to be someone you’re not because, spoiler alert, clothes won’t hide your true self (especially after a few drinks).


wedding dress on hanger

Don’t: Treat the Date Like a Wedding Reception

Unless you’re actually crashing a wedding reception on your first date like you’re cosplaying Melanie Griffith and Harrison Ford in Working Girl (kudos for the creativity), there’s absolutely no need to dress like you’re the guest of honor. 

This means leaving the overly flashy jewelry and the “I’m ready for the Oscars” gown at home. Subtlety is def more sexy. Go for “I thought this through,” not “I spent six weeks planning this outfit.”


green and blue umbrella

Obscure Don’t: Ignore Weather Reports

Nothing spells romance like showing up looking like a drowned rat or with icicles hanging from your nostrils. A weather check can save you from being miserably underdressed or sweating profusely through your carefully thought-out layered look.


pink tank top, cream slacks, gold earrings and gold rings

Do: Choose the Right Undergarments

Underwear is the base layer of any good outfit, and it is not only about avoiding visible panty lines or having to adjust a bra strap that keeps escaping from your top. 

It’s about wearing what makes your outfit look its best, and you feel your most confident. Whether it’s a supportive bra, seamless underwear, or shapewear that makes you feel like a goddess, the right undergarments are a must.


orange workout outfit with bomber jacket

Don’t: Be a Walking Billboard

Unless your date is at a comic con convention or you’re absolutely sure you both love that obscure indie band, and it’s a nod to that, save the logo-heavy apparel for another time. 

First dates are about getting to know each other, not seeing how many brands or logos you can wear at one time.


t-shirt, sweatpants and sneakers

Do: Have a Sense of Humor About It

Yes, it’s super admirable to make a good effort for your first date fashion choice, but please don’t lose any sleep over achieving sartorial perfection. If you spill wine on your shirt or find out you have lettuce in your teeth, try to laugh it off. 

Being able to handle little mishaps with humor is way more attractive than any designer outfit (unless it’s Tom Ford circa his Gucci days—that’s more attractive).


Takeaways

While clothes might maketh the man (or woman), they certainly don’t make a good relationship! Take a deep cleansing breath, wear what makes you feel like the best version of you, and go have fun! 

After all, the best accessory you can wear on a first date is confidence (so cheesy but so true). And maybe, just maybe, keep the experimental ensemble for the second or third date.

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