The Ultimate Guide to Choosing What to Wear on a First Date

man looking at clothes in closet with question mark next to him

The thought of going on a first date can stir up a mix of feelings. You could feel eager and excited, a little bit anxious, or wondering what the heck you should wear! Fear not, first date havers—we’ve prepared the ultimate guide to choosing your first date outfit.

Whether you’ll be getting to know each other over a cup of coffee or demonstrating your mini-golf prowess, these ensembles are sure to leave a great first impression. Did we mention those count? They do! So keep reading below to find our top tips for selecting what to wear on a first date and 10 handpicked looks for practically any first date venue!

Choosing the Perfect First Date Ensemble

The outfit for your first date should be a real representation of your personal fashion sense, considering the purpose of your date is to learn more about it. Before even deciding what you are gonna wear, think about the mood you are in and the vibe you are hoping to achieve throughout the date—then pick the clothes that reflect this. This approach can change up any tension and butterflies into eager anticipation. Naturally, there are additional pieces of advice to consider as you get ready for your first date:

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Where is the Date?

Dodging a wardrobe blunder on your first date is super important. This means the setting of your date should influence your outfit decision. Looking and feeling your best in what you wear is a must, so think about where you are meeting up. Are you going for a casual coffee date? Stick to something cozy and laid-back. If you’re dining at a high-end restaurant, it’s time to put on something a bit more formal, but make sure your footwear is comfy for an evening walk should the date go past dinner!

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Consider the Season When Choosing Your Outfit

Picking an outfit that suits the season involves more than just making sure that you’re dressed appropriately for the weather. It gives you a chance to play with the specific colors, fabrics, and prints that are popular during that time of year. Velvets and deep, rich colors, for instance, can bring a cozy yet sophisticated vibe to a fall or winter date.

Meanwhile, for spring, think about incorporating light fabrics and vibrant prints, such as florals, in bright or soft pastel shades. Remember to check the weather forecast before you head out and consider bringing a coat—unless you’re hoping for a romantic gesture of them offering theirs.

man trusting his instincts

Trust Your Instincts

When deciding on an outfit for a first date, let your intuition lead the way. Choose a couple of adjectives that describe how you want to feel and the overall atmosphere you want to create. Let these descriptive words serve as your outfit’s base—they can act as a useful filter, helping you in rifling through your wardrobe to find the pieces that resonate with your chosen words and avoiding those that don’t.

Now, onto what you should wear to make a great first impression on your first date!

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The Coffee Date

A coffee date is a great opportunity to start the romantic sparks in a relaxed setting. It’s one of our favorites because it allows for easy conversation without the commitment of spending a huge chunk of time together. But if things are going really well, you have the option to extend your time together. And if that happens, choosing an outfit that’s both fashionable and adaptable is the way to go.

Planning to transition from sipping lattes to exploring the city? Don’t forget to bring along sunglasses and wear shoes that won’t slow you down. Wearing layers is also a smart choice—this way, you’re comfortable no matter how the date unfolds.

steak and mushrooms

The Dinner Date

It’s our firm belief that everyone’s wardrobe should include at least one of the following: a timeless midi dress or a classic blue suit. This guarantees that when you’re invited to a dinner date, you can bypass the outfit anxiety and go straight for these reliable choices. We also stand by the idea that it’s impossible to be overdressed (within reason), particularly for a first date, and opting for a chic dress or suit will for sure leave a lasting impression. And let’s not forget about footwear—making a great impression starts with your shoes. A pair of cute kitten heels or retro-inspired penny loafers will perfectly complement your look.


The Movie Date

Heads up: Avoiding the faux pas of arriving at a movie date in what we refer to as “stand-only pants” (pants that are super tight or solidly constructed and aren’t really comfortable to sit in) is a no-no. Go for an outfit that’s both stylish and comfy enough to relax in through an entire movie—which is at least two hours.

While your mind might jump to athleisure as the obvious choice for that first date impression, try stepping it up a notch. Knitwear, like soft sweaters or cute two-piece sets, provides the perfect blend of comfort and class. They’re just as cozy but bring a little more flair to your look. And they have the added bonus of being super soft to the touch, which might just encourage a bit of snuggling over the armrests.

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The Brewery or Bar Date

If you’ve really been through it this week, a date at a bar or brewery is just the ticket to raise your spirits—yes, we went there with the pun, and we aren’t sorry! The formula for the ideal outfit is a simple one: Jeans paired with a cute top equals an unbeatable ensemble for any bar or brewery setting. We suggest leaning towards darker shades such as black, navy blue, or even red.

Transitioning from work to your evening out? Elevate your daytime outfit to nighttime chic with the addition of a fitted leather jacket or a pair of statement boots. And remember, the right accessories can make all the difference.

putt putt golf

The Putt Putt, Bowling Alley, or Arcade Date

Planning your first date at the mini-golf course, bowling alley, or arcade? This is your opportunity to show off both your gameplay and fashion sense. Since you’ll likely be moving around and standing for most of the date, choosing an outfit that combines comfort with style is of the utmost importance. Going with the old, reliable duo of jeans and sneakers will serve you well; it is not only practical but can also be spruced up for a more date-worthy look.

To add a little more sophistication to your casual look, consider throwing on a tailored leather bomber jacket or a warm flannel shirt. This not only levels up your outfit but also provides an extra layer should the evening turn cool if you are out in the elements.


Be Yourself

Our last tip for choosing a first date outfit is the easiest: just be you. Yes, it’s totally cliché, but being genuine in how you present yourself is the most important part of any date, whether it’s the first or fifth.

Clothing on its own may seem trivial, but it takes on more importance when it’s viewed as an expression of your identity. Your outfit should be a reflection of your personal style that shows your date a glimpse into who you are. So, choose an outfit that really feels like you!

Choosing what to wear on a first date takes a little prep work, strategy, and personal taste. Your clothes can communicate confidence and charm and provide a window into who you are–and make a good first impression that can boost the likelihood of another date!

Molly Davis
Molly Davis

Molly is an East Coast writer who lives on West Coast time. She’s been in the journalism field for over 20 years — newspapers are her first love but she’s finding digital media to be just as fun and challenging as print! When she’s not giving therapist-quality dating advice, she’s curled up watching movies, reading, or volunteering at local dog shelters.