What do you wear on a first date? Sure, there’s no secret fashion formula or magic one-and-done look that will guarantee a night of effortless convos and instant chemistry. But there is something to be said for showing up ready to stun in a style that is totally you. That slinky slip dress, for example? It’s your go-to for girls’ night out, but when it comes to date night dresses, you find yourself questioning its appeal (to layer or not to layer?). There’s no doubt in our minds that you have all the right tools to put together an outfit that will slay, but sometimes you just need that little bit of extra something to kickstart your confidence and put your mind at ease. Whether you have a casual coffee date or a swanky dinner in the books, we’ve scouted 20 flirty and fun dresses and jumpsuits that will solve all your first-date outfit dilemmas, so you can focus on what’s important (like navigating a potential Tinder nightmare).
1. Free People Embroidered Austin Dress ($148): A casual coffee date is the perfect time to show off your impeccable everyday style. We’re swooning over this airy peasant dress that’s on trend without being overdone. Pair it with a skinny scarf, suede lace-up flats and a jazzy cross-body bag, and get ready to schmooze over cold brew and laid-back coffee house tunes.
2. Halston Heritage Strapless Midi Crepe Dress ($275): Hello, gorgeous. Heads will be turning when you step out in this marigold dream. Balance out the bold yellow hue with elegant drop earrings or a statement cuff, and opt for natural-looking makeup for a fresh-faced look.
3. Finders Keepers Blow Your Mind Romper ($160): Sometimes, less is more. With its clean lines and timeless stripes, this playful romper strikes just the right balance of sophistication and fun. Not to mention, this staple piece is perfect for strolls along the boardwalk or bike rides along the beach. Accessorize it with modern hoop earrings, block heels and your award-winning wit, of course.
4. & Other Stories Braided Dress ($145): Whether you’re catching a flick under the stars or shucking oysters by the sea, your date will find it hard to keep their eyes off of you when you add this fiery red number to the mix. Pull hair back into a sleek topknot and layer on a few gilded accoutrements for a look that’s anything but short on panache.
5. Topshop Floral Print Jumpsuit ($80): A picnic paired with live tunes (the dream) calls for casually cool pieces that allow you to kick back and relax. Skip the short hemlines (you don’t want to fuss with them while sitting in the grass), and slip into this free-spirited floral jumpsuit instead. Let the good vibes flow with ankle-strap clogs, beach-babe waves and a bright red pout.
6. Madewell Striped One-Shoulder Dress ($128): Ward off wardrobe conundrums with this flirty one-shoulder stunner. Dress it up with heels and an embellished clutch, or play it cool with sandals and an Insta-worthy arm party.
7. Sunday in Brooklyn Pineapple Midi Dress ($148): Calling to mind poolside cabanas and white sandy beaches, this pineapple print dress is a shoo-in for a sunset sail or dinner out on the terrace. Snag a pair of wedges and a quirky clutch, then get ready to twirl your way into your date’s heart.
8. Free People Kaitlyn Jumpsuit ($253): After-work drinks on the agenda? Take this sassy jumpsuit for a test drive. The culotte silhouette and high neck read sophisticated and chic, while the halter neckline shows off just a peek of skin.
9. Floreat Livia Halter Dress ($138): LBD who? Black is always classic, but why play it safe when showcasing your fun-loving personality looks this good? Teamed with berry lipstick and a leather jacket, this vibrant cocktail dress is a hero piece in disguise.
10. & Other Stories Dragon Fruit Jumpsuit ($95): Who says you have to rock a dress to nail your date-night look? Wow your wooer with a printed romper that pays tribute to your gutsy fashion sensibilities. Dress it up with asymmetric earrings and embellished heels for a bit of gallery hopping or a gig downtown.
11. Article & Prima Midi Dress ($76): One of this season’s hottest trends — the ’90s-inspired halter — gets a ladylike makeover just in time for your big night out. The pale blush hue of this pleated hybrid dress lends it a romantic feel that just might make sparks fly. Wear it with neutral sandals and a metallic clutch for dinner and a show, or maybe even an impromptu go around the ferris wheel.
12. Flynn Skye Bella Floral Print Maxi Dress ($206): Dressed to impress takes on a whole new meaning when you have this swoon-inducing dress on standby. Channel your inner goddess with a perfectly applied cat eye, a dainty pendant necklace and metallic steppers, then watch as your date’s jaw drops.
13. New Revival Stretch Denim Tie-Waist Jumpsuit ($119): It takes a lot to spark your interest, and dinner and a movie just aren’t going to cut it. A rendezvous at your favorite Saturday flea market is more your style, and, of course, you need the right duds to go along with it. A jumpsuit with throwback appeal and a pair of platform sandals check all the boxes for scouting out vintage finds. Don’t forget the classic aviators and a Jane Birkin-approved straw bag!
14. Mystery Plungin’ Open Back Romper ($78): When all else fails, a flowy boho romper with an OMG-worthy neckline will always do you right. Case in point: This printed kimono-sleeved number will take you from tapas and small talk to an unforgettable night on a rooftop terrace like that. A pair of coveted gladiator sandals, swingy tassel earrings and a statement clutch may or may not be in order.
15. & Other Stories Striped Paneling Dress ($125): Cue the compliments: Expect all eyes to be on you when you don this bold striped dress for a much-talked-about play or dinner at that five-star spot. Style with sleek baubles that amp up the dress’s high-fashion feel, then drape a leather jacket around the shoulders for a slightly more casually cool edge.
16. Zara Limited Edition Ballet Dress ($100): Let this glitzy golden dress do all the talking. The shimmery fabric and flowy silhouette say you’re glamorous, easy-going and fun all rolled into one. Round out this scene-stealing look with a bold red lip and pointed-toe heels for a fabulously feminine look that isn’t messing around.
17. Pepin Annalee Off-the-Shoulder Dress ($298): Whether your first date is a group hang at your BFF’s backyard bash, a round of mini golf or a seaside picnic with your toes in the sand, this pretty printed dress is about as easy-breezy as it gets. Windswept locks and a choker or fringe-flecked earrings are non-negotiable.
18. Zara Floral Print Jumpsuit ($50): You’re cutting edge, but you still like to keep it real — show off that duality with this ruffle-trimmed culotte jumpsuit that’s both flirty and fashion-forward. Accessorize it with unique vintage finds and block heels for a getup that’s just as intriguing as you are.
19. ASOS Cami Pleated Midi Dress in Stripe ($78): The night is young, and you’re looking extremely stylish in this striped midi dress. Pull out all the stops with colorful tassel-trimmed heels and a statement cuff, then prepare to paint the town red.
20. Mango Side Pockets Dress ($70): If you do decide to pull out the ol’ LBD, make sure it’s one with plenty of personality. The trend-right high neckline, asymmetric hem and pockets (yes, pockets!) on this twirl-worthy number add endless RN appeal to an otherwise classic design.
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