Question: I'm not a kid anymore, but my footwear screams of adolescence. How should I edit my shoe collection so I look more mature?
Your choice of footwear speaks volumes and is something that both your bosses and women definitely notice.
If all your regular shoes are named after athletes and are more at home on, say, the basketball court than in the boardroom, it's time to update your look.
For work, one style that's always appropriate is the lace-up oxford. Every grown-up male should have a pair in his closet.
Brooks Brothers and Ralph Lauren make great conservative ones. If you'd like a little more pizzazz, try something from Paul Smith or Dolce & Gabbana.
For something in-between in terms of style and price, check out Aldo -- yes, the shoe store in every mall in America. Buy one pair in brown for khakis and earth tones, and one in black for everything else.
If you like a more casual look, consider any style of loafer from classic designers like L.L.Bean and Florsheim.
But since loafers scream preppie, either dress the part -- i.e., slim khakis (Unis), a gingham button-down shirt (J.Crew) and a solid tie -- or wear them with a pair of colorful socks from Paul Smith for a hint of irony.
Outside the office, you need one stylish alternative to the dress shoe. You can't go wrong with a desert, or chukka, boot, which works equally well with casual slacks or jeans.
Clarks, The Generic Man and John Varvatos offer among the best. Splurge on a pair that will last years, because they'll never go out of style.
Of course, sneakers are the cornerstone of every man's weekend wardrobe. However, you don't always have to wear cross-trainers.
There is no better classic-yet-cool sneaker than the Converse. Traditionalists favor Chuck Taylor (high or low-top) and will wear them until they look like something you would've seen on James Dean.
If you want sneakers with a little more style, choose a Jack Percel low-top. White, black or navy works with everything from jeans to a casual cotton suit, or you can make a bolder statement with a red pair, which goes great with black and neutrals and looks amazing once it's really worn in.
Common Projects makes what I call a grownup sneaker -- a little pricey ($400+) but well worth the investment. This simple low- or high-top has no decoration except for an uber-subtle gold-foil serial number on the side.
For a change of pace, consider a natural-colored gum sole. This stays cleaner-looking for much longer than a white sole and lets the world know that you've got game.
Annie Psaltiras is a Los Angeles-based fashion stylist whose clients have included Vanity Fair, Flaunt, GQ and Rolling Stone. Her regular celeb clients include Justin Timberlake, Aaron Eckhart and Zach Galifianakis.
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