Ankle boots (with a heel): Should you want to make a colorful statement, take inspiration from Gwyneth and the Parisian fashion show goer, above, with red pair, like these ones from Rag & Bone. I love these Madewell boots, because they're feminine, polished and everyday practical. Same goes for these by Tory Burch. You still can't go wrong with Isabel Marant's Dicker boots--classics in my book. (Urban Outfitters makes a $49 version.) If you need a dressy pair that's suitable for work and evening--more pump-like, if you will--try these from Rosegold, which feature a sleek snakeskin panel, or these edgy-cool pair from 3.1 Phillip Lim.
Knee-high boots: Givenchy's spats boot (pictured above) is the season's cult (and almost-sold-out-everywhere) boot. Zara makes a version. I'm partial to timeless styles, ones that will work year after year, like these from Jimmy Choo, or this pair from Steve Madden, with a wraparound ankle band, or these from Chloe. For a flat-heel, I'd go with these from Rachel Roy.
Over the knee: Daring and bold, these boots look best with short shirts, or over tight, tight jeans. Try these by Jean-Michel Cazabat or Alexander Wang.
Shootie: These low-cut boots are almost shoe-like, hence the name. I love this style, because they go with everything and will work season after season. This investment pair by Miu Miu is a forever shoe. L.K. Bennett's cap toe version also offers major mileage. Ditto this casual burgundy hued tassel-trimmed Cole Haan.
Photo: 1. Phil Oh, 2. Phil Oh, 3. Tommy Ton, 4. Sincerely Jules, 5. Phil Oh, 6. Phil Oh, 7. Phil Oh, 8. Vanessa Jackman