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10 Pairs of Shoes Worth the Investment

These shoes are not cheap, but they're also not trendy. Instead, they're enduring, the sorts of booties and pumps and brogues you'll wear for falls and winters to come. So once you crunch the numbers on the price-per-wear scale you either come out even...or way, way ahead. (Buying just one pair will greatly improve your current cold weather wardrobe, we promise.)

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Swap out ho-hum nude pumps for these badass alternatives (part Jetson, part Joan Jett) and you'll incite more than a few cases of shoe envy at the next cocktail party.


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Savillle Row-inspired and super-expensive looking—like something out of the Prince of Monaco's closet—they're way more worthwhile than standard saddle shoes or solid-color brogues.

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You'll be getting these day-to-night boots resoled every few years for the rest of your life. (That, I think, is the sign of an amazing investment.)


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Detailed from the back and classic from the front, they're an interesting yet enduring staple for weddings and holiday parties.

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So much cooler than the typical neutral-colored ankle boot, but every bit as versatile.


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It's not just the Downton Abbey vibe that gets me. It's also the way that wearing these eye-catchers would let me slack off with the entire rest of my outfit. Always.


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I don't know if I'm cool enough to wear these shoes (I mean...that heel), but I really, really want to be. I wouldn't wear them every day, but once a week? Realistically, yeah.


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Not the prettiest, but maybe the most necessary: shearling-lined yet polished, they'll let you trek around post-blizzard without looking like Snooki or a clueless college student. And that's sorta priceless.


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The ultimate people pleaser, combining the dude-appeal of tall boots with a ladylike shape your mom would love. (And that refined, fancy-looking cap toe detail? I kind of think everyone loves that.)
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For weekends and errands and flats-necessary times, these Love Story-like loafers can't be beat. Pair them with a corduroy blazer or a graphic print sweater to echo their slightly kitschy tone.

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