Wondering What to Wear on a First Date? Here Are 14 Outfits to Try

If you’re looking for something that can take you straight from your desk to the bar, this getup should do the trick. The long blazer keeps you looking professional for a day of meetings, then transitions to become a light jacket for your after-dark plans. Plus, a knit midi will show off your curves but won’t get you in trouble with HR. Finish with a clutch that’s large enough to hold your phone, wallet and mascara for a touch-up at the end of the day (no plethora of totes required).

Shop similar styles: Reiss blazer ($425; $160); Simon Miller dress ($190); The Volon bag ($775); Sam Edelman sandals ($80)

Keep things cute and casual in your favorite jeans and a pretty top with statement sleeves. Have fun with embroidery, embellishments, a vibrant print or lace (though you might want to avoid anything that could accidentally dip into your cappuccino). Strap on a pair of heels or stick to flats—simply choose the footwear that feels most inherently you.

Shop similar styles: Pilcro and the Letterpress top ($98); Good American jeans ($175); Gucci bag ($1,290); Nine West heels ($80)

Unfussy is the way to go for an outdoor date, so pick out a pretty floral frock and step into shoes you can take a few laps in (classic white comfy sneakers are a solid standby). Pro tip: Top off this outfit with a denim jacket that you won’t mind using as an impromptu picnic blanket.

Shop similar styles: Love, Fire dress ($49); Bardot dress ($179); La Maison Talulah dress ($299)

Jewel tones like deep ruby, emerald, sapphire and amethyst look good on almost every skin tone, and they always look expensive (yes, even if your dress is from Old Navy). Burgundy in particular feels femme, sexy and romantic, making it one of our favorite color options for a cozy corner table at the cool new bistro in your neighborhood.

Shop similar styles: Theory top ($255; $102); Sally LaPointe pants ($1,650; $646); Frances Valentine bag ($228); Vince Camuto heels ($110; $60)

Breathable, flowing fabrics are key here, not just because they look beautiful while you sway and move to the music, but because you don’t want to end the night as a sweat-soaked mess. The other key: practical footwear. Sure, your fave strappy heels are cute, but they won’t feel so great after a few turns on the dance floor.

Shop similar styles: Anthropologie dress ($148); Free People boots ($188)

Time to work those layers! Choose a sweater that you can pop over your frock during the movie, then drape it artfully over your shoulder for the walk home.

Shop similar styles: Faithfull the Brand dress ($189); Lou & Grey sweater ($80)

Being comfortable enough to move around is important for an active date, so choose jeans you can squat in. Seriously, you don’t want to exchange “nice to meet yous” while worrying about your vintage Levi’s ripping at the crotch. Pair your denim with a breezy blouse that accommodates a normal bra (i.e., avoid anything strapless or adhesive) and go for flats. Sure, you could wear sneakers, but flats have a slightly dressier feel that will transition seamlessly to post-game dinner or drinks.

Shop similar styles: See by Chloé top ($265); Agolde jeans ($178); & Other Stories bag ($69); Jewel Badgley Mischka flats ($90)

Bright colors, like daffodil yellow, dusty rose or kelly green, will help light up your face even more than the mood-setting candles on the table. Add straight-leg pants that won’t feel constricting after a full plate of pasta, and wear foolproof heels, sandals or boots in a hue that coordinates with your top. That, my friends, is the perfect way to communicate your attention to detail.

Shop similar styles: J.Crew blouse ($88; $53); Levi's pants ($98); Mansur Gavriel bag ($325); Dolce Vita heels ($125)

Now’s the time to get a little…jazzy. You don’t want to feel overdressed, but an invitation to a live performance does deserve some level of glam. Mix a patent leather, velvet or lamé blouse with a more low-key bottom, such as a denim or cotton skirt, to strike a balance between dressy and down to earth.

Shop similar styles: Dolan top ($218); Toast skirt ($175); MICHAEL Michael Kors heels ($99)

Don’t be fooled by midday temperatures at ground level. It will always be at least a few degrees cooler on a rooftop after the sun has gone down and the wind has picked up. Try a figure-hugging sweater with a midi skirt for some extra protection from the elements, without sacrificing your signature style.

Shop similar styles: Chinti and Parker sweater ($450); Halogen skirt ($69); Naturalizer heels ($60)

A professional sports game can be a really fun way to get to know someone new. But don’t feel pressured to be all “rah-rah, team spirit!” Skip the sporty tee or official team jersey and color-block with the team colors instead. You’ll fit right in at the game and feel comfortable at a cozy bar afterward.

Shop similar styles: Avec Les Filles jacket ($139); Lulus top ($45); Madewell jeans ($80; $65); Schutz boots ($225)

Show off a bit of your own artistic inclinations with a creative print or bold color pairing. It doesn’t matter if you rock a patterned midi skirt with a cropped striped top or don a bold knit with floral trousers, so long as you wear shoes that won’t echo through the exhibit with every step. The horror…

Shop similar styles: Gucci jacket ($4,800); J.Crew turtleneck ($37); Rebecca Taylor skirt ($325); Sarto by Franco Sarto shoes ($109)

Realistically, you should try to get as much information as possible about what type of date this might be. But if your suitor is remaining mum, you can at the very least find out what type of footwear is required. (No one will be happy if you show up in towering stiletto booties for a bike ride through the park.) For the rest of your outfit, stick with a tried-and-true ensemble you’ve worn before, whether that be a slip skirt and a cozy knit or bright red pants and a concert tee, à la Coterie member Monroe Steele.

Shop similar styles: Old Navy blazer ($50; $45); ASOS Design T-shirt ($23); I Am Gia pants ($125); J.Jill shoes ($119; $70)

There’s a reason everyone always says you can never go wrong with an LBD. This wardrobe staple will always leave you looking chic, elegant and ready for anything that comes up. (Except maybe an impromptu hike in the woods, but we feel pretty confident you already know how to dress for that.)

Shop similar styles: Free People dress ($108); Steve Madden boots ($102)