10 First Date Outfit Ideas to Feel Like Your Best Self

model in white ankle boots, Diarrablu Printed Pants


First dates can be nerve-wracking and exciting all at once, making a great outfit all the more important so you can feel as confident as possible. When planning out a look, staples that make you feel like your best self 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 and fun accessories will catch your date’s eye and undoubtedly make a great impression, too, be it a uniquely cut top, pants with a bold print, colorful heels, or sculptural earrings.

Depending on the date, you can totally get away with casual pieces if that’s your comfort zone. White sneakers are the perfect offset to a feminine dress; likewise, a pair of pastel kitten heels looks amazing as a focal point with a T-shirt and jeans. 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 casual vibe, or balance out a billowing crop top with a long pair of cut-off shorts or loose-fitting bottoms

If of-the-moment trends are the way to your heart, by all means, channel that energy on a first date. A bustier-inspired top will read fashion-forward and fresh, as will a pretty puff sleeve. Here for all things ’90s? Anchor your look with sleek leather pants, a minimalist heel, or both. Whatever your taste, keep scrolling for 10 stylish first-date outfits that work for coffee, drinks, dinner, and beyond.

A Pretty Top and Jeans

outfit 1

Design 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.

A Matching Top and Skirt Set

outfit 2

Design Tiana Crispino

A matching set takes the stress out of outfit planning, and is right on trend in 2021. For drinks or dinner, style this coordinating ribbed top and skirt with delicate sandals and a modern mini bag.

Leather Pants and a One-Shoulder Top

outfit 3

Design Tiana Crispino

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

A Frilly Dress and Sneakers

outfit 4

Design Tiana Crispino

A frilled 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.

A Cropped Blouse and Shorts

outfit 5

Design Tiana Crispino

Balance out the boldness of a billowing crop top with a pair of long shorts and lace-up sandals.

A Bodysuit and Printed Pants

outfit 6

Design 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.

A Bustier Top and Slip Skirt


Design Tiana Crispino

A slip skirt is fail-safe for any date. Pair yours with a bustier top and lace-up espadrilles for a low-key, summery vibe.

A T-Shirt and Jeans

outfit 8

Design Tiana Crispino

Despite being go-to staples, a T-shirt and jeans 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.

A Midi Dress and Sandals

outfit 9

Design Tiana Crispino

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

A Jumpsuit and Heels

outfit 10

Design 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.

Lead image products provided by Commando and Diarrablu.

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