First Date Clothes for Dummies

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).