What Should I Wear With . . . ?
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Jeans  Brown loafer • Like this Lacoste Concours Tassel 3 Loafer, $150 at nordstrom.com • Even dressed up, denim is a casual fabric. A slip-on loafer works with or without socks, while a golden, cognac-hued brown creates a nice contrast with blue denim and feels less dressy than black, mahogany, or oxblood. |
Khakis  Boat shoe • Like this Sperry Top-Sider Authentic Original Boat Shoe, $74.95 at nordstrom.com • “Khakis are in between jeans and dress pants, and men often go too formal or too informal,” says Andrews. A boat shoe is perfect—both it and khakis are preppy basics. “It looks especially right in DC because it has an East Coast feel.” |
Shorts  Brown driving moccasin • Like this Prada Suede Penny Driving Shoe, $480 at nordstrom.com • The deconstructed suede leather and hand-stitching make this casual enough to wear on a bare leg. Because socks are a no-no, choose a brown or tan shoe, which blends into your skin tone; black looks jarring. |
Tuxedo  Black patent-leather or polished-calf oxford • Like this Boss Black Mellio Plain Toe Oxford, $225 at nordstrom.com • Look for a style that’s the very definition of elegance: a sleek silhouette with some sheen but no perforations and no more than five eyelets. “Let it be understated so it virtually disappears,” says Andrews. |
What Not to Wear
To err is human. Avoiding shoe faux pas is divine. Here’s more advice from Nordstrom’s Gregg Andrews.
 “Mandals” • “Unless you live in Hawaii, anything braided or strappy or high up the foot like a fisherman’s sandal looks cheesy,” Andrews says. “If you must, go with one wide band or a simple flip-flop.” |
 Brightly colored leather shoes • “Attracting attention to the feet is not the smartest thing for a man to do. If you want to express your personal style, put the focus up toward your face.” |
 Clogs • “There are a lot of comfy, stylish shoe options out there. Clogs are not one of them.” |
 Converse sneakers with a tux • “It seems like a desperate attempt at being nonconformist, hip, and cool. There are other ways to do that, like opting for a white dinner jacket.” |
