James Dean made jeans cool years ago; generations will wear them for years to come, and you’re going to rock them today. Jeans are classic for good reason: They go with everything, including most shoe styles. Although you can wear any pair of flats with your favorite jeans without drawing disapproving stares, pairing the right flats with the right jeans guarantees you’ll draw stares for all the right reasons.
Straight and Boot-Cut: Flattering for All
Just as a killer pair of flats suits every foot, straight-leg or slightly boot-cut jeans flatter most body types. Better yet, jeans of this style pair well with just about any pair of flats you own. Pick a pair of jeans in a dark wash and have them tailored if needed. Ideally the hem skims the back of your foot just above the floor — just a bit shorter makes your legs look stumpy, any longer and the jeans drag on the ground and hide your shoes. Straight or slightly flared jeans are perfect for everyday wear. Pull on cozy moccasins to run cold-weather errands or pick animal-print ballet flats with a neutral top.
Cropped and Rolled: Versatile
If you feel prim one day and rock-and-roll the next, stock your closet with a few pairs of cropped jeans. These styles show a bit of skin and display your personal sense of style. Wear slim capris with a cardigan and delicate ballet flats, or pair studded loafers with slouchy, rolled-cuff boyfriend jeans and a T-shirt. Because cropped jeans hit above the ankle, this style is the right choice when you want your shoes to be the star of your outfit. Try mixing a neutral top, cigarette pants and a pair of metallic, bejeweled or patterned flats.
Skinny: Play Up Your Shape
Runway models don’t have dibs on skinny jeans. Body-hugging jeans can be flattering on the petite, the plus-sized and everyone in between. Choose a pair with plenty of stretch. Heed some advice from “Real Simple” and avoid a pair that bunches on your calves or sags at the waistband. After you find your perfect skinnies, choose your shoes based on your style icon for the day. Channel Audrey Hepburn with a trim button-up shirt and a pair of preppy oxfords, or opt for a beachy Hollywood starlet look with canvas slip-ons and a few layered tank tops. Avoid pointy toes in skinny jeans unless your goal is to make your feet look bigger than they really are.
Trouser: For Work and Play
For a weekend work event, a PTA meeting or dinner out, leave your everyday jeans at home and pick a pair of trouser jeans. Typically made of sturdy denim, these straight- and wide-legged pants are as dressy an option as you’ll find on the jeans rack. The width of the leg means much of your foot is hidden, so rounded toes are lost. Pick flats with pointed toes. They extend the line of your leg, making you look tall and ladylike. Paired with a blazer or silky blouse, you’ll look so pulled together no one will realize how comfortable you feel.