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13 Cute First Date Outfits That Will Boost Your Confidence

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Updated on 11/01/23 01:59PM

Byrdie editor Aimee Simeon wears a brown bodysuit, patterned pants, and long braided hairstyle — Dion Lamar Mills for Byrdie

First dates can be both nerve-wracking and exciting, which makes a great outfit all the more important so you can feel your most confident. When planning a look, your go-to staples are an ideal starting point, whether that’s a T-shirt and jeans, a pretty dress, a matching set, or a jumpsuit. Eye-catching pieces make a great impression, too, be it a uniquely cut top, printed pants, or sculptural earrings. Depending on the date, you can opt for elevated casual looks, like white sneakers with a dress, or a T-shirt and jeans with a pair of pastel kitten heels. And speaking of jeans, denim is definitely first-date approved: Try a pretty top and colorful mules with vintage-washed straight legs for a put-together vibe, or balance out a billowing crop top with cut-offs. If trends are the way to your heart, channel that energy with a bustier-inspired top, quiet luxury staples, or '90s-inspired sleek leather pants. Whatever your taste, keep scrolling for 13 cute first date outfits that will help you look and feel your best for coffee, drinks, dinner, and beyond.

For a Low-Key Meetup

Red puff-sleeve top, light wash jeans, and yellow kitten heels — Design by Tiana Crispino

If jeans are your comfort zone, dress up your favorite pair with a pretty puff-sleeve top and colorful mules. Great for a picnic or a low-key night on the town, this first date outfit exudes effortless confidence.

For Dinner and Drinks

Brown top handle bag, string sandals, and orange matching set on model — Design by Tiana Crispino

A matching set takes the stress out of outfit planning, so it's no wonder this trend has had major staying power over the last few years. For drinks or dinner, style this coordinating ribbed top and skirt with delicate sandals and a modern mini bag.

For Outdoor Activities

Straight leg jeans on model, red leather jacket on model, and v-neck collared beige sweater — Byrdie

If you're going on a first date in the fall, your plans might involve a pumpkin patch, cider at an orchard, or an array of other outdoor activities in the crisp weather. To stay cozy and casual but still put-together, layer a polo sweater under a statement leather jacket, then pair it with some trusty denim.

For a Night on the Town

Gold textured hoop earrings, straight leg leather pants, and white scarf top on model — Design by Tiana Crispino

Embody ‘90s minimalism for date night in these slick leather pants paired with a strappy white top. Delicate gold earrings are a sleek finish made even better with dewy makeup.

For a Whirlwind Adventure

Ruffled dress, gold chain necklace, and white sneakers — Design by Tiana Crispino

A ruffled dress reads feminine but not overly sweet when paired with white canvas sneakers for a daytime date or relaxed meet-up. A polished gold anklet makes for a sleek yet unexpected accent that highlights the intention you put into your easygoing first date outfit.

For a Chilly Night Out

White trench-style coat, brown knit dress on model, and brown suede knee-high boots — Byrdie

Sometimes you find yourself spending time outdoors during a cold-weather date, whether you're walking from dinner to a cocktail bar, enjoying a near-empty park, or checking out holiday lights. You obviously still want to look nice while staying warm, so layer a tailored coat over a knit dress, then complete the look with tall boots.

For Bringing the Drama

Light wash denim shorts, heels with mint green straps, and woman wearing black billowing top — Design by Tiana Crispino

Balance out the boldness of a billowing crop top with a pair of long shorts and lace-up sandals. Whether you're headed to a picnic or a dive bar, this casual yet intentional look is sure to impress.

For the Party Date

Gold medallion necklace, brown and white patterned pants, and brown bodysuit on model — Design by Tiana Crispino

You can’t beat a bodysuit for an effortlessly stylish date night outfit—team yours with zebra-print pants and a gold pendant necklace for guaranteed impact.

For a Breezy Evening

Floral crop top, light blue slip skirt, and strappy espadrille flat sandals — Design by Tiana Crispino

A slip skirt is fail-safe for any date—and it provides so much versatility to rewear for any occasion. Pair yours with a bustier top and lace-up espadrilles for a low-key vibe that feels especially romantic on a warm, breezy evening.

For the Last-Minute Date

Brown structured t-shirt, white jeans, and kitten heel sandals — Design by Tiana Crispino

Despite being go-to staples, a T-shirt and trousers are anything but boring when modern details like padded shoulders and a corseted waist are part of the equation. Pastel kitten heels steer the date night outfit in a dressier direction while maintaining ease.

For a Sunny Afternoon Date

Multicolored crystal earring, black flat sandal, and white maxi dress on model — Design by Tiana Crispino

Midi dresses exude easy romance, making them ideal for first date outfits. A style featuring a peekaboo back reads decidedly fresh for warm-weather dates. Play up the midsummer aesthetic with colorful earrings and flat sandals.

For the Fancy Event

Black blazer on model, black silk halter dress, and nude kitten heel — Byrdie

Have you ever found yourself agreeing to be a wedding date or found someone who suggested the fanciest bar you could think of? Just because the location has a dress code doesn't mean you need to stress too much about your first date outfit. A classic LBD will work wonders here, especially when paired with an oversized blazer and chic nude pumps.

For Impromptu Drinks

Woven bucket bag, brown heels with straps, and white jumpsuit on model — Design by Tiana Crispino

It doesn’t get easier than a jumpsuit when dressing for a date in a hurry. To make things easier, stick to a timeless neutral palette—you’ll look relaxed yet elevated for dinner or drinks.