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.
Shows a tasteful amount of skin.
This neutral-toned pattern is a fail-safe option.
This dress says "sweet and easygoing."
Pair this timeless black dress with your favorite summer sandals.
You’ll be comfortable and relaxed all night in this tie-waist dress.
Layer a denim jacket over this printed dress for a chic, laid-back look.
Give off subtle French-girl vibes in this knit dress.
It’s okay to play it safe with a neutral color.
Not your average LBD.
You’re sure to have a good night in this flirty floral dress.
Tie straps are the perfect flirty detail.
Dress up this floral number with loads of dainty jewelry.
These florals are not just for summer.
For the modern minimalist.
Feeling flirty but still want to look cool? Reformation always has you covered.
Layer this cool dress over a T-shirt for a casual date, or wear with block heels if you're grabbing drinks.
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.
-
The Ashley Olsen Way to Make Simple Black Coats Look Chic, Not BoringIt's so easy, yet so impactful.
-
Looking Stylish This Fall Means Wearing Your Pretty Dresses With This Unexpected ItemHere's how to master the look.
-
Anyone Can Wear a Cardigan, But Only Fashion People Wear Them Like *This*Take note.
-
5 Street Style Trends From Milan Fashion Week That Will Be Everywhere This FallTake notes.
-
This Dated Denim Pairing Is Suddenly the Chicest Way to Wear Jeans for Fall 2025Easy and stylish.
-
Everything Who What Wear Editors Saw, Wore, Did, and Ate During NYFWLet's dive in, shall we?
-
Paris Hilton's World: Her Pink Motorola Razr, Favorite Y2K Looks, and What 11:11 Media Means to HerA glimpse into the life of this savvy entrepreneur.
-
This Simple Fashion Person–Approved Layering Technique Changed the Way I Wear My BasicsEffortlessly cool.
