Our Guide To The Chicest Hill-Friendly Heels

Although we Bay Area ladies might look longingly at soaring 4-inch+ pumps, let’s face it: We live in a city so precariously hilly that strutting around in sky-high heels just doesn't make sense. While this predicament can often lead to an abundance of dowdy gals in fugly flat boots (you know who we’re talking about!), it doesn’t have to. Give your leg a little lift with our top picks for cute and comfortable heels, 3-inches-and-under, that won’t have you shuddering in disgust or reaching for your practical flats.
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There’s no way you’re getting up Taylor Street in stilettos. Instead, opt for these sturdy, super-cute espadrilles by Spanish company Castaner. Metier owner Sheri Evans and shop girl Rebecca Goldschmidt swear by this pair for long days on their feet.
Castaner Lace-Up Espadrilles, $173, available at Metier, 355 Sutter Street (between Stockton Street and Grand Avenue); 415-989-5395.
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These strappy wonders just reek of good, springtime vibes thanks to their zesty seafoam hue. With a mere 2.5" boost, you’ll be able to power walk laps around Dolores Park without a stumble.
Matiko Modern Cutout Wedge, $148, available at Urban Outfitters, 80 Powell Street (between Ellis and Eddy streets); 415-989-1515.
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Acrimony shop owner Jenny Chung can attest: These strap-tastic, open-back shoes are made for walkin’. "They have the perfect 2.5" heel and are easy to slip on, but won’t slip off," she says. "I wore them for a 6-hour photo-shoot and was just fine."
LD Tuttle The Neon Heel, $550, available at Acrimony, 333 Hayes Street (between Franklin and Gough streets), 415-861-1025.
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Full disclosure: These heels are actually over three inches. However, they are crafted by local industrial designer-turned-shoemaker Martha Davis, who is just as passionate about function as she is about fashion, and makes sure all her shoes are completely S.F.-friendly.
Martha Davis Tie Wedge, $495, available at Metier, 355 Sutter Street (between Stockton Street and Grand Avenue); 415-989-5395.
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Because a girl cannot live on black heels alone, this striped, collegiate-feeling version features a rubber sole and an almost-3-inch heel that just might be able to take you from the Castro to Noe, sans MUNI.
Naughty Monkey Peek A Boo Pump, $55, available at Endless.
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We dare you to walk around town without getting a compliment on these sorbet-colored cuties. While the stacked heel looks high, it’s actually a very do-able 2.1".
ASOS Shamble Block Heel Town Shoe, $71.72, available at ASOS.
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We’ll never understand 4-inch-plus desert boots. This pair, by comfort-first company L.L. Bean, comes in at the perfect 2.5" mark, features traction-focused soles, and latex cushioning for extra pavement-pounding relief.
LL Bean Desert Bootie, $169, available at LL Bean.
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When in doubt, stick with designer Rachel Comey, known for making supremely hip footwear, like this Hitch bootie, which is as classic as it is cool and comfy. Conifer owner Amy Mautz says she treks up Webster Street daily in them.
Rachel Comey Hitch Bootie, $368, available at Conifer, 2848 Webster Street (between Union and Green streets); 415-922-1892. Super Steal: Mention this article in-store at Conifer this week and snag this ridiculously comfy (and stylish!) pair, plus all other Rachel Comey styles, 15% off!
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