Your Ultimate Guide On What to Wear to Any Date

Whether you're linking up with someone from the apps for the first time or you're taking your sweetheart out for your millionth date night since marriage, you've gotta look good. Actually, not just good—you've gotta look your damn best.

Date night is when your sweatpants and baggy tees need to take the backseat, and your best fits need to come out and do their best work. Take it from me, a girl who has admittedly gotten the ick from poorly-dressed guys before—what you wear matters! Your date is certainly going to be putting in effort with their look, so it's time for you to step up to the plate, too.

That being said, the next question is, inevitably, "What should I wear?" Well, that depends. Different dates call for different vibes, but we're laying out the most probable scenarios for you below, along with what you should be wearing to each one. So long as you're dressed like this, cuffing season will be an absolute breeze.

For the Elevated Wine and Dine

Dinner and drinks calls for a put-together, semiformal look. I'm not saying you need to whip out your best tux or anything, but being sat across from somebody at a restaurant gives them a lot of time to take in what you're wearing, so make sure it's something good. A button-down, blazer, and some nice pants will do the trick. Keep things from teetering into the black tie territory with loafers and white socks.

Everlane Relaxed Poplin Shirt

Now 60% Off

$35 at Everlane

For the Chill Coffee Date

The "let's grab a coffee and walk around" date gives you plenty of leeway with your fit. Go for something comfortably chic that looks like you tried, but not too hard—the key here lies in accessories. A fun cardigan or jacket will do the trick, along with some relaxed jeans, a hat, and casual shoes (but leave your scuffed-up kicks at home).

NN07 Mika 6620 Floral-Jacquard Knitted Cardigan

$305 at MR PORTER

Cos Regular Fit Midweight Brushed T-Shirt

$39 at cos.com

Levi's 550 Relaxed Fit Jeans

$69 at Levi

Dr Martens 1460 Mono Smooth Leather Lace Up Boots

$170 at Dr. Martens

Q Timex Reissue Navy Dial Bracelet Watch

$179 at Todd Snyder

Corridor New York New York Cap

$55 at corridornyc.com

For the Park Picnic

When you're outside, you have to keep things breathable and breezy. Linen pants will be your best friend, and you can dress 'em up with a funky polo or camp collar shirt. And because I know you aren't making your date carry all the picnic supplies, you're going to need a tote bag, too.

Tombolo x Marie de Buttet Terrycloth Shirt

$148 at Tombolo

J.Crew Tall Broken-In Tank Top

$24 at J Crew

Percival Linen Everyday Trousers

$165 at percivalclo.com

Adidas Samba OG Shoes

$100 at ADIDAS

Garrett Leight Hampton Clip M Sunglasses

$185 at garrettleight.com

Brooklinen Tote

$25 at Brooklinen

For the Drinks and Dancing

For a sleek, sexy night out, black and leather are going to be key. Wear something you feel confident in—good-fitting pants, sharp Chelsea boots, and a sick leather jacket will probably do the trick. And because there's nothing quite like a glint of jewelry under dark lights, don't be afraid to accessorize, too.