THE DARK BROWN OXFORD
Nothing ruins a look like a pair of clunky, square-toed shoes. They look dated even if you just bought them, and your whole outfit falls flat. The fix? A pair of dark brown leather oxfords with a round toe. They’re modern and sophisticated, and go with nearly everything in your wardrobe.
Works best with: Business or casual dress. Think navy, gray, and charcoal suits; tweed jackets; work-appropriate jeans (no distress marks, tears, or open flies!); corduroys; khakis; and gray flannel.
Keep them new: Have shoes resoled when your heel is wearing thin—and don’t let it wear down to the leather because you’ll end up paying more
Don’t bother with black patent leather shoes you’ll only wear a few times in your life, unless you’re a red carpet regular or constantly getting married. Instead, opt for a pair of narrow black leather shoes—they’re just as polished and elegant, but also look good with your work clothes. Two birds, one shoe.
Works best with: Tuxedos, dark jeans, and navy, gray, and black suits.
Keep them new: Use cedar shoe trees (when you’re not wearing them, silly). Cedar absorbs moisture and helps shoes hold their shape. And remember: No one has ever regretted having leather shoes polished. Make that $4 investment regularly.
When it’s so cold you can feel the wind through your laces, it’s time to switch to Chelsea boots. Since they’re laceless, they keep your feet and ankles warm, but unlike most boots, they’re dressed up enough to wear around the office. Bonus: These integrate Nike Air technology, so they’re extremely comfortable.
Works best with: Casual dress like jeans and cords. Or dress them up with dark jeans, a button down or sweater, and a tweed jacket.
Keep them new: If there’s snow on the ground, there’s probably salt too, which ruins leather. Remove stains with a 50/50 mixture of white distilled vinegar and water, and wipe dry. Use a water and stain protective spray.
The two biggest complaints we hear about loafers: 1) “They’re too preppy”; and 2) “They remind me of Ronald Reagan.” Fair enough, but if you look into the actual history of loafers, you’ll realize that long before Northeastern prep schoolers got their feet on them, they were simply the best shoe for loafing around. They’re leisure shoes and they should be really comfortable. Now, many brands are giving them a more modern silhouette. Exhibit A: This slim pair, with its attractive gathering and top-stitching detail.
Works best with: Jeans and khakis; shorts in the summer, but no socks.
Women love beat-up boots on a man. They remind us of that too-cool-for-school dude (literally, he never came to school) we had a crush on as teenagers. And even if you don’t have an edge, they’ll give you one. Like, Brad Pitt. He has about a dozen kids, but still has an edge, you know?
Works best with: Extremely casual dress: weathered jeans and T-shirts, olive cargos and Henleys. These will be your go-to weekend boots.
Tip: Never wear these to the office, unless you work for John Varvatos or Kenneth Cole. In which case, maybe even try something a little daring like pairing them with a slim-fit suit.
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