What to Wear on a First Date
Preparing for a first date can be super nerve-wracking. From choosing where to meet, to picking out the activity you’ll do together, to planning your outfit and figuring out how to style the rest of your look, there’s certainly a lot to think about! That’s why we put together this list of our favorite tips for deciding what to wear on a first date. Thanks to breezy jumpsuits and flirty date night dresses, you’ll be ready for a fun time in no time.
Dress for the Occasion
First and foremost, your first date outfit should suit the venue. Just as you wouldn’t wear a strapless dress to a corporate job interview, you probably wouldn’t wear a T-shirt and jeans to a fancy dinner date. Pay attention to where you’re headed for your date and what you’ll be doing and then start building your look from there.
If You’re Going for Coffee
A daytime coffee date is a casual kind of get together that calls for a no-fuss outfit to match. Instead of spending hours getting really glam, opt for comfy styles that look (and feel) equally effortless.
- Pair a flowy, floral dress with chunky white sneakers for a look that gives off major cool-girl vibes.
- Dress up a lightweight white tee with a snake print skirt and platform sandals for an easygoing yet elevated look.
- A black turtleneck looks super chic when it’s tucked into high waisted jeans and paired with low heels and tousled waves.
An easy, breezy look will have you feeling comfortable and confident–and is sure to leave a positive first impression on your date.
If You’re Heading to Happy Hour After Work
Sometimes you don’t have even a moment to change between work and a weeknight date, but that doesn’t mean you’ll end up looking stuffy. Plan a stylish outfit in advance and make a few tiny tweaks to meet up with your date in time to catch those meal deals!
- Pair a crisp shirt dress with a bright pair of shoes for a look that easily transitions from day-to-night. Undo a button or two to give it an even flirtier look.
- Jumpsuits are extremely flattering and look just as good for work as they do for play. Experiment a little with color, or pick a crowd-pleasing print like plaid and then switch from mules to heels after you clock out for a dressier look.
- Tuck a chunky sweater into a leather-like skirt for a sophisticated and versatile pairing. Opaque tights and over the knee boots are playful enough for after hours but still sophisticated for the workday.
No matter what outfit you choose, switching up your accessories can give your workday outfit the boost it needs to last until date night ends. Add some sparkly earrings and you’re good to go!
If You’re Going Out to Dinner
A special dinner is a classic choice for a first date. It gives you both time to get to know each other, but the flexibility to not order dessert if the chemistry isn’t right! For a dinner date, style outfits with special touches that show your playful side without giving away too much.
- A sophisticated LBD is one of the most perfect types of date night dresses you could choose. Freshen up the look with a pair of sparkly tights, black booties and a cushioned headband.
- Mix a floral print midi dress with comfortable wedges and an envelope clutch for an effortless date night look.
- Dark wash jeans become super sophisticated when paired with a jewel-tone top, crisp black blazer and classic black pumps. Finish with a pair of sparkly earrings and a sequined crossbody bag.
If You’re Going Somewhere Unconventional
You might choose to spend your first date somewhere unexpected. Whether it’s an exercise class together, a sporting event or a visit to the museum, unconventional dates call for a dress code of their own.
- If you’re taking an exercise class together, dress for comfort in attire that hugs your body but doesn’t reveal too much skin.
- If you’re catching the game, pick your team’s colors and wear chunky sneakers for a sporty outfit that looks cool, too.
- If you’re going to the museum, high waisted jeans look trendy when paired with a white tee, chunky cardigan and block heel booties.
Showing Your Personality
One of our favorite tips for how to dress classy has to do with your own inner confidence. Over anything else, your personality and ability to be true to yourself is what will make your first date look really shine. No matter where you’re headed, you’ll have a better time if you pick an outfit that you feel your best and, most importantly, most like yourself in!