Dress to Impress — What to Wear on a First Date

Chloe MullinerChloe Mulliner
Chloe Mulliner
9 min read
Published in Dating 
Check out our guide if you’re wondering what to wear on a first date. We have all the best tips to help you make a good first impression!

When planning a first date, the goal is to make a good first impression. That involves showing up on time, minding your manners, and engaging in conversation, but it also requires looking presentable. However, you don’t have to be a fashionista or up to date on all the latest fashion trends to achieve this. Looking presentable simply means wearing an appropriate outfit that makes you feel comfortable and confident for your first date. 

Not sure what to wear on a first date? Don’t worry; we’re here to help you dress to impress. In our guide on how to dress on a first date, we offer all the best tips to help ensure you look your best. 

Things to Consider

If you’re wondering how to look more attractive on your first date, it’s just a matter of understanding some of the do’s and don’ts of first date outfits. Follow along for our tips and tricks:

Do Wear What Makes You Feel Good

What do both women and men find attractive? Confidence! So, when you’re deciding what to wear on a first date, think about the clothes in your wardrobe that make you feel like a million bucks. 

Maybe you have a blue sweater that perfectly matches your eyes, a pair of pants that does wonders for your booty, or a top that always receives compliments when you wear it. Looking attractive is often less about what you wear and more about how you wear it, so search your closet for the clothing and accessories that put some pep in your step. 

Don’t Wear an Outfit You Haven’t Worn Before

Sure, buying an entirely new outfit for your upcoming date might sound like a good idea, but there’s nothing worse than hobbling around in a new pair of shoes that are giving you blisters or feeling like you’re going to burst in jeans that you haven’t broken in yet. If you’re tugging at your sleeves or squirming in your skirt all throughout your date, you may not come off as laid-back and confident as you were hoping. 

To avoid this, consider wearing something that you’ve already worn before or doing a test run in an outfit ahead of your first date. Wearing something you’re comfortable in will allow you to spend more time giving your attention to your date and less time fussing with your clothes. 

Don’t Try to Be Something You’re Not

If you’re a cowgirl boots gal, don’t show up to your first date in six-inch stilettos. And if you’re a flannel-shirt kind of guy, don’t wear a silk button-down on your first meet-up. Your first date isn’t the time to completely alter your appearance or style, as doing so might come off as ingenuine or inauthentic. It’s best to stick with what you already know you look good in and what feels natural for you to wear so you exude comfort and confidence. 

Do Dress Modestly

When wondering what to wear on a first date, sometimes, it’s best to leave some things up to the imagination. In other words, don’t arrive in an ultra-low-cut shirt or a barely-there skirt. While we’re sure you look amazing, wearing overly sexy or exposing clothing can be distracting and may even give your date the wrong idea about you. 

Instead, go for something a little more modest. For example, put on a pair of slim-fit jeans that showcase your long legs, or go for a shirt that shows off your toned arms. We recommend wearing clothing that accentuates your best traits without showing too much skin on your first date. 

Don’t Wear Clothing with Stains, Rips, and Holes

If you’re wondering how to look more attractive on your first date, begin by inspecting your clothes for any stains, rips, or unintentional holes. Showing up in dirty, smelly, or ratty clothing is one sure way to offend your date because it suggests you didn’t care to practice proper hygiene or put in an effort to look presentable. 

To avoid seeming like a careless slob on your first date, be sure to put on clean clothes free of any snags, rips, holes, or stains. 

Do Express Your Sense of Style

Perhaps our biggest tip regarding how to dress on a first date involves letting your own sense of style shine. If that means wearing big, bright jewelry, donning your jacket with the patches, or stepping into your red Doc Martens, do it! Don’t feel like you have to stifle who you are in order to make a good first impression

Remember, you want your date to appreciate and accept who you are—eccentric accessories and all—so try to be true to yourself when it comes to deciding what to wear on your first date.

Do Wear Layers

If you’re sweating bullets because you’re baking under an outdoor heater or violently shivering because the sun just set, you’re going to have a hard time focusing on your date. To avoid being uncomfortable due to the surrounding temperatures, consider wearing layers on your first date. For example, wear a tank top or light shirt under your sweater so you can peel off a layer if it gets warm, or bring a cozy jacket in case the temperature drops. 

Date-Specific Outfits

Aside from the above tips, there are a few more considerations when deciding what to wear on a first date. For instance, the first date venue or activity may also play a role in choosing an appropriate outfit. Follow along for some additional advice to help ensure you make a good impression on your first date. 

Casual Dates

Just because you’re going somewhere laidback for your first date, like a coffee shop or brewery, doesn’t mean you shouldn’t give your outfit any thought. After all, casual does not mean sloppy! 

You don’t need to dress to the nines (in fact, we encourage you not to), but you should put effort into your attire, even if that just means throwing on a clean blouse or ironing your pants.

Cocktail Dates

When grabbing drinks at a cocktail lounge or hitting up happy hour at the pub for a first date, this is an opportunity to take your outfit a step up from what you might wear on to a coffee shop. That might mean swapping out your flats for a pair of heels or changing from a t-shirt into a collared shirt. Or maybe you’ll throw on a pair of earrings or leave your worn-in baseball hat at home. 

Again, you don’t need to dress up for this kind of date, but it doesn’t hurt to make some minor upgrades to elevate your outfit. 

Sporty Dates

For those who are going on a sporty or outdoorsy first date, dress for the occasion. For instance, don’t show up wearing inappropriate shoes like high heels or flip flops if you’re going on a three-mile hike. 

In this case, it’s more important to wear clothing that will serve you well rather than to show up in your favorite outfit. Depending on the nature of the date, you’ll probably want to wear something loose or stretchy that allows you to comfortably move around, whether you’re playing frisbee at the park or riding bikes to the bay. Also, be sure to wear layers in case you break a sweat or get chilly during your sporty first date. 

Fancy Dates

If you’re going on a first date to an upscale restaurant or fancy event, it’s crucial to research the venue and not only inquire about the dress code but also understand what it entails. After all, there is a big difference between business casual, semi-formal, formal, and black-tie dress codes, and arriving in the wrong attire could be embarrassing (and a major faux pas!). For example, if the dress code is business casual, khakis and a collared shirt or a skirt and blouse would be appropriate, but if it’s a black-tie event, tuxedos and gowns are expected. 

When in doubt, consult with your date to help prevent yourself from showing up in the wrong attire for your first outing. 

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