My first-date track record is hit-or-miss, but I chalk that up to chemistry and not what I wear (thank you very much). When I’m picking out what to wear on a first date, I’m a creature of habit. Having spent a few years navigating dates with strangers, I’ve made a habit of deliberately dressing “normal,” which for me usually entails jeans with a T-shirt or dressy top and a pair of comfortable shoes. Despite what that description may lead you to believe, that’s not to say I don’t put in the effort. Simply put, as a distinctively low-key person, I’ve realized that I want a first impression to be an honest representation of who I am.
Still, since dating is a process that’s a bit of a closed-feedback loop (it’s rare and frankly weird to get a review afterward), I was curious to know how other women dress for a first date. So I decided to reach out to single friends on social media and hear about their habits for date-night dressing. The hope is that crowdsourcing other women’s tricks for a first date will make things just that much easier for you the next time it’s your turn. Read on to learn more!
Comfort is definitely my top priority when getting dressed for a first date. If I feel good about what I’m wearing, I know that my attention will be at 100%, and I won’t be distracted by the need to adjust my clothes during the date. My favorite combination recently has been a simple top that has a hint of trendiness, like a sweetheart or asymmetric neckline, paired with some relaxed trousers (my top wardrobe classic). I usually finish it off with a few fun jewelry items that can act as conversation starters.
The kind of top I’d buy for date night but wear for everything else.
Every closet needs a pair like these.
Trendy and actually really wearable.
“I like to show my personal style on a first date while keeping it fun and flirty. My go-to outfit formula in the winter is leather pants, platform Dr. Martens, and a cute top that shows some skin (but not too much). Accessorizing is the key to keeping the outfit true to my style. I always wear bright-red lipstick, a standout piece of jewelry—either a gold necklace or statement earrings—and a mini purse to keep the look sophisticated and feminine. Lastly, I like to wear a bright-colored coat for a fun pop of color to complete the outfit.” — Emma
Emma is really selling me on this pretty Ref find.
Aritzia’s Melina pants are the GOAT of faux leather.
Every fashion girl’s wintertime staple.
Definitely one of the more affordable It bags of the moment.
“My go-to outfit for a first date is extremely simple, and there’s a science behind it. Being stressed out trying to put a sophisticated outfit together before heading out for the night is not going to help you radiate your best energy when you arrive. I always tell my friends that they’re going to only see you from the waist up for the majority of your time together, so just focus on finding tops that flatter your figure without being too revealing. That’s why I always choose a statement top and flattering jeans, gravitating toward pairs that make my legs longer. Oh, and high heels are a must no matter how tall he is.” — Sierra
This screams fall.
There’s a reason these jeans have the cult following that they do.
WWW readers are especially keen on these cute mules.
“My go-to first-date outfit is always casual but chic. I lean toward an all-black ensemble because I feel the most confident and comfortable. A little bit of leather never hurts.” — Isabel
I love the boxy fit of this jacket.
An A+ basic.
I can’t get over how luxe these look.
The heel gives them an elevated feel (literally and figuratively).
The perfect outfit enhancer.
“I reach for an oversize shirt or a dress with tights and finish it with knee-high boots and a classic blazer.” — Kelly
It’s not every day I’d call a blazer pretty.
How to go from the office to a date 101.
There’s never a bad time to stock up on these.
Look cool, feel comfortable.
I’ve worn a version of this outfit more times than I can remember on a first date, and it’s never failed to make me feel like the coolest version of myself. I like to add personality to the jeans-and-a-cool-top formula by opting for a pair of checkered jeans—I like that they let my personality shine through and usually earn me a compliment.
A moto jacket makes me feel cool AF.
This top was made for wearing with jeans on a night out.
I love these so much that I bought them in a second color.
Western-inspired ankle boots are another personal favorite.
“My perfect first-date look is always a great-fitting pair of jeans with an off-the-shoulder top.” — Zoe
Exposed shoulders are underrated IMO.
For that perfect fit.
Ultra sleek.
Classic but modern. What more could you ask for in a bag?
“When picking out a first-date outfit, I always put focus on choosing a pretty top that flatters my collarbone and jewelry fit of my personal style. Since we’re typically sitting at a table or bar, that’s what they’ll be seeing the most, and I keep the rest simple.” — Kendall
I can confirm the fit of this top is so good.
Currently eyeing these.
Sweet and simple.
“I usually go for a long-sleeve midi dress with sneakers. Comfy, cool, and cute.” — Danielle
Red is a power color—why not wear it on a first date?
Comfort is key.
My co-worker Aniyah has impeccable style and shared that her date outfit consists of a sleek midi dress layered atop knee-high boots. It’s simple but sophisticated, and now, I want to try it out for my next date.
Simple but also a little sultry.
I’m in love.
“Silky button-down shirt with a cute lace bra peeking through with a pair of cool pants. A good pair of raw denim and low-heeled mules for something more casual, and then to dress it up a tad, I’ll go for flared pants that match the top for a monochrome moment.” — Vanessa
Silk shirts are always a good idea.
A hint of trendiness is all you need sometimes.
Next up, 12 Fall Date-Night Outfits You Can Absolutely Wear at Home
