Date Night
Oct 30, 2017

17 Foolproof Dresses to Wear on a First Date

by Michelle Scanga

Should you show some leg? Is pink too girly? How much cleavage is appropriate? Is this print too bold? Yes, we all have these thoughts when it comes to deciding what to wear on a first date to make the right impression, impress your date, and ultimately have a great time. Avoid wearing anything too fussy that needs constant attention to adjust and re-adjust. You’re going to want to be comfortable in whatever you end up wearing, freeing yourself up to focus on getting to know your date. When in doubt, go with the simple option. There’s nothing wrong with paring back your style a bit here—why not save that bold pattern for date number two? Lucky for you, we have 17 charmingly appropriate dresses that will solve all your first-date outfit dilemmas.

Scroll through to shop the dresses that are sure to make a great impression.

This neutral-toned pattern is a fail-safe option.

Casual Tea Dress

Casual Tea Dress

This dress says "sweet and easygoing."

Agnes Dress

Pair this timeless black dress with your favorite summer sandals.

Tied Mini Dress in Black. - size 0 (also in 2)

Diane von Furstenberg

Tied Mini Dress in Black

You’ll be comfortable and relaxed all night in this tie-waist dress.

X REVOLVE Oslo Dress

Faithfull the Brand

Layer a denim jacket over this printed dress for a chic, laid-back look.

Zou Bisou Knit Mini Dress

Zou Bisou Knit Mini Dress

Give off subtle French-girl vibes in this knit dress.

Tie Waist Dress in Black. - size S (also in XS,M,L)

Tie Waist Dress in Black

It’s okay to play it safe with a neutral color.

Lana Dress in Black. - size XS (also in S,M,L)

Lovers + Friends

Lana Dress in Black

You’re sure to have a good night in this flirty floral dress.

Draped floral dress

Violeta by Mango

Draped Floral Dress

Dress up this floral number with loads of dainty jewelry.

Delta Dress

Feeling flirty but still want to look cool? Reformation always has you covered.

Straight-Neck Midi Dress

Silence + Noise

Straight-Neck Midi Dress

Layer this cool dress over a T-shirt for a casual date, or wear with block heels if you're grabbing drinks.

Dress With Lace and Frill

Try a high neck if you're showing a little leg.

Next up, seven date outfits that are both stylish and comfortable.

This post was published at an earlier date and has been updated by Anna LaPlaca.

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