The Ultimate Style Guide To Dressing For A First Date

You’ve stumbled upon the man of your dreams (or so you hope) after a chance encounter at your local coffee shop, through the recommendation of a mutual friend, or swiping right on your favorite dating app. Now it’s time to take a leap of faith and meet up for your first date. So, what should you wear?

By Anna Hartman4 min read
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Nearly as important as avoiding the topic of your ex, being on time, and giving yourself a good old fashioned pep talk beforehand, choosing an appropriate outfit can make or break a first date. The cliché  “first impressions are everything” is a cliché for a reason: it’s true

You’ve likely spent hours agonizing over every possible scenario in your head, from being stood up at dinner to finding out that he’s a real-life Catfish. In 2022, dating is more difficult than ever. Although I can’t physically be on your date giving you a thumbs up from behind a suspiciously agile shrub in the corner or analyzing his body language for red flags, I can try to lessen the burden you’re facing when getting ready. 

Go with the Confident and Comfortable Choice

So, let’s jump right into it, shall we? Firstly, let’s begin with the most important tip: choose an outfit you feel confident and comfortable in. Wearing an uncomfortable outfit on a first date can not only add to your nerves, but it can also make you feel self-conscious and distract you from creating a meaningful connection. If you’re fidgeting with the hemline of a too-short dress, showing excessive cleavage, or feeling so unbearably cold that you can’t feel your fingers, the overall energy of your date isn’t going to feel natural and effortless. Your guy could interpret these mannerisms to mean that you’re feeling uncomfortable in his presence or uninterested in the conversation. 

You may assume that you’ll hold a man’s attention better with a low-cut blouse, but wearing something that’s considered risqué may actually hurt your chances at finding love. According to the experts, “Women who wear overly revealing outfits on a first date are often perceived as being superficial and promiscuous instead of demure and seductively sexy.” 

Instead, let’s work on getting dressed in a classy and sophisticated outfit that’s going to help you radiate confidence and focus on the goal at hand: discovering if there’s a genuine spark. While emptying your savings on a new, fancy dress for each date may not be realistic (or advised), I promise that you can easily piece together a feminine and stylish look with items already hanging in your closet.

If you own these six closet staples, you can create a perfectly chic outfit for your first date without spending a dime. Whether your date is a formal setting or more casual, having a classy midi dress, neutral heels, a timeless bag, feminine flats, a flirty blouse, and everyday jeans is a guaranteed way to build an outfit that leaves a lasting impression – in a good way.

On the other hand, if you’re not at the point in your life where you own pieces that you feel comfortable and confident in (I know I didn’t at the time), I can totally understand if you feel defeated while looking into your closet in anticipation for a first date. If you are ready to invest in timeless items that you can mix and match, my guide below covers two shopping options for each wardrobe staple. 

6 First Date Wardrobe Staples

1. Classy Midi Dress

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2. Neutral Heels

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3. Timeless Bag

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4. Feminine Flats

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5. Flirty Blouse

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6. Everyday Jeans

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Next up, let’s tackle the itinerary for the date and choose outfits accordingly. It seems that modern dating has made people quite creative when it comes to first date experiences. Whether you’re meeting with a potential match for a quick coffee to see if there’s any chemistry, you find yourself on the other end of a Facetime call with a handsome French man, or you have a classic dinner reservation downtown, I’m covering outfit inspiration for six different occasions.

For a Coffee Date

To err on the side of caution, it’s best to dress casual, yet polished for a coffee date. Showing that you tried too hard with a cocktail dress, red lipstick, and heels will surely come across as desperate. On the other hand, rolling out of bed in an oversized tee and leggings to potentially meet the man of your dreams is going to read “sloppy and childish.” 

To put it simply, it’s best if you’re dressed as if you have somewhere to be after the coffee date. Jeans and a sweater or blouse paired with boots or flats is the perfect combo for a casual morning or afternoon meet-up. 

For Cocktails

Similar to the coffee scenario, since this isn’t a formal dinner date, I would recommend going with a fancier blouse or cropped jacket as opposed to a dress. Since you’re just grabbing cocktails, you don’t want to appear as if you’re expecting an invitation to dinner afterward. If he wants to see how stunning you look in a midi dress, he’s going to have to properly ask you to dinner next time. 

For a Dinner Reservation

For a dinner reservation, you certainly could go the route of wearing an LBD. That’s always a safe and classy bet, especially for a first date. However, if you want to stand out and show off more of your personality, I would suggest adding a pair of statement earrings or choosing a style element that is anything but boring (like this dress with pockets). 

For Going Out with a Group

Depending on what time of day and where you’re meeting with the group, you have a lot of creative freedom with this one. You can either opt for a sophisticated blouse with jeans, a colorful flowy dress, or an understated daytime set and flats. My advice is to read the room and ask your girlfriends what they’ll be wearing – you don’t want to be entirely over or under dressed. 

For a Facetime Date

“What to wear on a Facetime date”...please hold while I add that to the list of things I never thought I would write about. Not to age myself, but I don’t even think Facetime was around when I was in the dating scene (Tinder and Bumble definitely weren’t). While the times have changed quite a bit over the past 10 years, if you’re crushing on someone in a different state or country, a Facetime date may truly be your best option to see if you want to pursue a relationship. 

Since you’ll likely be attending the virtual date from home, polished but understated is the overall vibe you want to stick with. Choosing a relaxed top like a nice sweater, silky button-down shirt, or informal blouse is ideal. 

For an Outdoorsy Date

Sometimes sitting down to coffee or dinner on a first date can feel a bit awkward. To avoid first date jitters and the inevitable awkward silence, planning an activity in a public place can give you something to talk about (people watching, common places and interests, etc.) and make the date flow more naturally. 

If you’re planning for lunch in the park, a hike up a local mountain, or a walk around downtown, the main focus when getting dressed needs to be your comfort. Check the weather forecast and opt for a matching workout set that isn’t too revealing, a casual daytime dress with sneakers, or a classy blouse with shorts and flats. 

Closing Thoughts

Whether you choose to reimagine pieces from your current closet, or invest in something new that excites you, hopefully this style guide has given you some insight into what you should wear on a first date. Harness your refined femininity by being prepared for the occasion with key wardrobe staples that make you feel comfortable and confident.

Lastly, an encouraging reminder to leave you with: you never know when you’re getting ready for your last first date. From firsthand experience, I can truly tell you that love finds you when you least expect it.

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