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.
Ali & Jay
Love at First Sight Mini Dress
Shows a tasteful amount of skin.
This neutral-toned pattern is a fail-safe option.
This dress says "sweet and easygoing."
Cooper & Ella
Agnes Dress
Pair this timeless black dress with your favorite summer sandals.
Diane von Furstenberg
Tied Mini Dress in Black
You’ll be comfortable and relaxed all night in this tie-waist dress.
Faithfull the Brand
Oslo Dress
Layer a denim jacket over this printed dress for a chic, laid-back look.
Free People
Zou Bisou Knit Mini Dress
Give off subtle French-girl vibes in this knit dress.
L'Academie
Tie Waist Dress in Black
It’s okay to play it safe with a neutral color.
Helmut Lang
Asymmetrical Mini Dress
Lovers + Friends
Lana Dress in Black
You’re sure to have a good night in this flirty floral dress.
Pixie Market
Beverly Shoulder Tie Ribbed Fit and Flare Dress
Tie straps are the perfect flirty detail.
Violeta by Mango
Draped Floral Dress
Dress up this floral number with loads of dainty jewelry.
Rachel Zoe
Meade Cold-Shoulder Floral-Print Silk-Chiffon Mini Dress
These florals are not just for summer.
Rag & Bone
Brighton Layered Gingham Poplin Dress
For the modern minimalist.
Feeling flirty but still want to look cool? Reformation always has you covered.
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.
Zara
Dress With Lace and Frill