Cheryl Shops

The exact provenance of cap-toe pumps is a bit murky, but most of the credit goes to Coco Chanel, whose nude shoes with a contrasting black toe had the always-welcome effect of elongating the leg. Like pretty much everything Chanel appropriated, the cap-toe pump is considered a classic, with a certain refined air. And after years of big, clunky platform pumps, ladylike single-sole pumps are making a comeback for fall, although if you're hopefully devoted to platforms—as I am—you still have options. The fun, fashion-forward spin on cap-toe pumps this season, however, is that they incorporate metallics. The overall effect is a little bit dangerous, but definitely sexy. And, well, you know how I feel about that.

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I love Prada, because she always interprets a trend (often one she herself starts) in a very intellectual way. This suede cap-toe pump balances femininity—the colors, the height—with a somewhat clunky shape and a not-so-sexy squared toe. Call it the thinking woman's pump.

Manolo Blahnik has ceded much of his It-Shoe ground to Christian Louboutin in recent years, but I tend to find his footwear more quietly sexy. The Camparicap Mary Jane takes his Sex and the City classic ("I thought these were an urban shoe myth!") and turns it up a notch.

Based on what Hedi Slimane is doing to the house of Yves Saint Laurent, I am nervous about the future of its wonderful, amazing shoe designers, who create beauties such as the Mae pumps. Let's hope PPR keeps them on the payroll.

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Michael Kors may be quipping his way to the bank right now, but the reason he's so successful is that he makes shoes like the Cynthia pump, which manage to remain both classic (neutral colors) and edgy (hidden platform, chain trim).

Sometimes I like to wonder WWMOD (What Would Michelle Obama Do?), and I think when it comes to this trend, it would be to wear J.Crew's Etta pumps, a fun take in that the body of the shoe is metallic and the toe is matte.

This Steven by Steve Madden Fearless pump is practically a no-brainer, but just in case you need extra persuasion, it's a classic black suede pump with a pointy toe and a perfect three-inch heel. The contrasting silver tip is just the icing on the proverbial cake.

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I'm drawn to these ASOS Pacey shoes not because of their name (best Dawson's Creek character of all time!) nor their price (a very affordable $55, currently) but because of the crisscross straps at the ankle. I have incredibly narrow ankles, which means pumps usually slip up and down on me; this style looks like it will stay perfectly in place.

I've decided I need to wear more white in the winter because, hey, you're only young once. These Danger Zone pumps by Chinese Laundry look icy-hot.

Also from ASOS, the Perry pumps are rather similar in shape to the Blahniks above, however the color is much more fun, and I think it will be the perfect antidote to the winter blahs. The price is also way more wallet-friendly.