First Date Clothes for Dummies

You’ve picked the perfect spot, you’ve got the script from Notting Hill committed to memory and you even remembered to wear deodorant. But, while those things are important, what you wear ranks just as high on the list. Show up at a nice restaurant in a ratty band T-shirt and she won’t likely care about the fact that you both love sushi and Fight Club; she’ll be too busy wondering which room of your parents’ house you got dressed in that morning.

Here are five first-date scenarios—from drinks at your favorite pub to a good old-fashioned walk in the park—and all that you need to dress to impress.

All dates have to start with a foundation, so investing in wardrobe staples is important. These essentials can be worn with each of these looks—keeping both you and your wallet happy.

Levi’s 527 Boot Cut Jeans in Tumbled Rigid ($58)
The right denim is key. A clean, dark rinse can be easily dressed up or down. Levi’s Boot Cut Jeans in Tumbled Rigid have a classic straight fit that looks polished but is still comfortable, and the dark rinse complements virtually anything, so no worries about color clashing (available at Levi.com and most department stores).

Chuck Taylor All Star Low Canvas in Elephant Skin ($50)
Chuck the chukka boots and just go for the Chucks. Even she owns a pair. Stick with a neutral color like the Chuck Taylor low canvas in elephant skin. Just… leave the ones with the scuff marks at home (available at Converse.com).

J.Crew Leather Roller-Buckle Belt ($39.50)
To belt or not to belt, that is the question. The answer is up to you. It’s not a necessity but if you decide to go for it, keep the hardware simple, like on J.Crew’s Leather Roller-Buckle Belt. And please keep in mind that your shoes and belt should not clash (available at JCrew.com).

A casual meet-up at a low-key pub is a great place to break the ice and get to know each other.

Calvin Klein Body Slim Fit Ribbed V-neck T-shirt in Light Beige ($19.99)
Don’t diss the T-Shirt. Believe it or not, women love your favorite, perfectly worn-in go-to just as much as you do—as long as you do it right. Keep it clean and simple. V-neck or crew, up to you. Try Calvin Klein’s Body Slim Fit Ribbed V-neck T-shirt. It’s comfortable and soft—in case she decides to get close (available at Calvinklein.com and most department stores).

Your girl more of the dinner and wine type?

Tommy Hilfiger Slim Fit Ramsey Shirt in Lapis Blue ($49.99)
Stick to a crisp button-down. Vertical stripes elongate the body for a flattering fit. You can wear Tommy Hilfiger’s Slim Fit Ramsey Shirt in Lapis Blue tucked in and belted—or not—depending on your restaurant of choice. If it’s on the fancier end,go for the belt (available at Macys.com and most department stores).

Aldo Tani Lace-Up Dress Shoes ($125.00)
And while Ellen DeGeneres may rock the button-down and sneakers look, please don’t. Try Aldo’s Tani Lace-Up Dress Shoes instead (available at Aldoshoes.com).

Express Skinny Silk Tie in Black ($39.90)

If you’re really trying to impress, add a tie. Express’ Skinny Silk Tie is slim and sleek,so it’s a bit trendier and doesn’t scream “I just got out of the office,” but it will give her something to pull you in closer with for that good-night kiss (available at Express.com).

So, you both love modern art. Or the theater. Or pottery (you must really like this girl).

Express Cotton V-neck Sweater in Blue Fin ($59.90)
You want to look classy, but not overdone, so opt for a sweater. Classic and comfortable, Express’ Cotton V-neck Sweater in Blue Fin will give you more time to talk about your love of Modigliani and less about your lack of fashion sense. That is, if you listen to us (available at Express.com).

Putting this look together will be a walk in the park—whether or not you’re going on one. Trying to win her that teddy bear at your local festival? Feeding the ducks at the zoo? (No really, you must really like this girl). Look good doing it.

Rugby Black and Blue Flannel Shirt ($79.50)
Meet your new favorite flannel: Rugby’s Black and Blue Flannel Shirt (available at Rugby.com). It’s warm and already has that perfectly worn-in feel.

Kenneth Cole Sagan Nylon Jacket in Black ($119)
Still too chilly? Add Kenneth Cole’s Sagan Nylon Jacket in Black as an extra layer of warmth. Offer it to her when she’s cold and she’ll be impressed by your chivalry—and your style (available at Kennethcole.com and most department stores).

Snagged tickets to see her favorite band or a baseball game? Now’s the time to wear that favorite band or team T-shirt of yours (just no holes please). Or take this opportunity to let your personality shine.

Horizon Mustache is the Key T ($20)
We like the Horizon Mustache is the Key T (available at Macys.com). It’ll give her some insight to your sense of humor. And who doesn’t love a mustache? (Note: mustaches are OK on your shirt. Not on your face. Unless you’re a cop…or Colonel Sanders).

Lucky Brand Twill Aviator Jacket in Mermaid ($149)
Can’t swing it with just a T? This rugged military-inspired jacket is the perfect top layer: Lucky Brand’s Twill Aviator Jacket (available at Luckybrand.com).