13 Cute First Date Outfits That Will Boost Your Confidence (2024)

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

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

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

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

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

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

Sometimes you find yourself spending time outdoors during a cold-weather date, whether you're walking from dinner to a co*cktail 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

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

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

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

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

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

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

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.

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