I’ll admit it: I don’t wear heels that often. It’s not that I don’t adore them — trust me, I can appreciate the candy red sole of a Louboutin and always manage to hit up the Hollywould sample sale. It’s just that I like them a lot more on display than on my foot. Finding sexy shoes that are actually comfortable enough to be sexy in is no easy feat.
There are, however, certain occasions where you will undoubtedly find me (and most women, for that matter) in stilettos: first dates, drinks with the ex, school reunions, fancy evening events, job interviews and important meetings, just to name a few. It’s really not surprising that Zappos sells more heels than flats at a 65 to 35 ratio. Heels simultaneously symbolize sexiness and strength, so it’s no wonder we sacrifice so much to strut in them. I think the author of this article in The Wall Street Journal (“Ferragamos to be Fired In” – how clever!) gets the psychology of it exactly right: “High heels…offer an inherent contradiction. They make us more fragile, but conquering them to stride alongside men in their sensible flats creates mystique.” Oh, how right she is!
I have to ask, though, do we really have to suffer in order to stay stylish in our stilettos? The answer is no. Okay, maybe “not always” would be more accurate. If you’ve been struggling with sore soles, but refuse to give up your chic high heels, consider these. They’re sexy, sophisticated and convey just the right amount of power without killing your foot – the key is the roundish toe. And just for the record, I've test-driven these recommendations. I pranced and strutted around my apartment — and the streets of NYC in some cases — and they really don't hurt (too bad, that is). The Mary Janes are only $79 from Nine West; the Calvin Klein Vida pumps pumps ($100) pinch a little at first, but adjust to your foot nicely; and the orange patent Enzo Angiolini Thrill slingbacks
slingbacks ($93) are simply fierce!
Have any good shoe recs? Please, share! And if you're still on the lookout for shoes that feel like nature intended, check out our guide to Comfort Shoes and our Pain Free Solutions.




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Sadly, I’m flat-footed, so even though I adore a great pair of heels, I’m forced to constantly carry emergency flip-flops. And let me tell you, my favorite little black dress does not go well with polka dot Havianas!
For us arch-impaired girls, the only sure-fire solution I’ve found are Foot Petals – cute, flower-shaped inserts that go right under the ball of your foot to give support and a little cushion action. They’re simply amazing! I put a pair in every heel I own!
Hey Jillybean — I flat feet, too! That’s part of the reason I don’t wear heels as much as I’d like to. You should really try the Nine West ones, though. I’ve had great luck with them. And thank for the Foot Petals rec. I’ve never heard of them, but I am going to look for them today!
Nice maryjanes, but I love the slingback!