10 Looks That Will Have You First-Date Ready

Dressing for a first date can be one of the most daunting tasks. Even when faced with a closet busting at the seams, we’ve all had that experience where we can’t seem to muster a single look. You want to wow, showing him you’ve made an effort, but fear coming on too strong with a fussy cocktail dress that you don’t quite feel like yourself in. If there was ever a time to try your hand at high-low dressing, it’s now.

Now that summer is almost here and—frankly—we’re all much more excited to leave the house for a few more dates than we were during last season’s arctic chill (pajamas and takeout on the couch just sounded so good…), it’s time to slip into something a little more presentable. Whether you’re making a denim look more tailored with the addition of a statement blazer and whimsical heels, dressing up in a silk skirt and camisole, or slipping into a pair of low-top sneakers with your skirt-and-blouse look, we’ve got some major inspiration when it comes to first date outfits. Check out our favorite first date outfit ideas below and shop them for yourself, romantic evening or not!

For the girl who loves the classics, consider jeans and a button-down shirt. Step it up a notch, though, by choosing raw-hem denim and a top that is cropped or has added detail to its silhouette, like ruffles or pleats.

For a look that’s after-hours-friendly but effortless at the same time, consider a silk midi skirt. Paired with a simple black camisole and strappy sandals, it’ll have you ready for any type of date, day or night.

Sometimes you just want to pull out all the stops and get dressed up. If that’s your speed, really go for it, choosing a dress with color and flair. Keep your accessories just as special, but balance out your look with more neutral tones or classic metallics.

Tailor your denim look with the addition of a blazer and, to really make it special, consider a bright stripe instead of solid neutral. Play up the whimsy with a graphic tee and heels with a contrasting pattern to your jacket.

Be your most comfortable self by mixing and matching your seasonal wardrobe staples. Grab that leather mini that goes with everything and tuck a brightly colored knit into the top to make it a little softer and cozier. Finish it off with ballet flats and a structured bag.

Preppy doesn’t have to be stuffy. In fact, some plaid and tweed staples can be dressed down for the younger generation just as they can be dressed up for your mom and grandmother. With the simple choice of a miniskirt shape, easy silk blouse, and sporty white kicks, you’ll make it your own.

For the color lovers, go all-out, but keep it understated in silhouette by sticking to the classics. With a pair of tailored ankle-cropped pants and slightly oversize sweater, you can try out all the colors in your crayon box.

Consider topping an all-black look with a brightly colored blazer. A pop of color is never more welcome than in blazer form, over cropped black pants and a simple camisole.

Reach for that easy breezy midi dress, but slip into a pair of statement heels that wow. Consider belting the dress at the waist as well for a little something extra.

Reach for that little black dress that you know gives you the most confidence of anything in your closet. For summer, pair it with lace-up sandals and a raffia or wicker bag.

What better confidence booster exists than putting together a stellar look? We're feeling more prepared already—how about you?