Here's the truth about shoes: Pricier designer pairs tend to hold up better than their cheaper knockoffs. Chalk it up to superior craftsmanship and leather. That's why I splurge on my mainstays, like the Stuart Weitzman 5050 over-the-knee boots with elastic back, perfect for fuller calves like mine. (For two weeks, starting on October 20, you can customize the heel on your 5050s at stuartweitzman.com.) The anytime, anywhere shoes featured here—warhorses, each of them—are available in wide-width or wide-calf sizes. And for some fun ideas about what to pair them with, check out my first fashion collaboration, with ModCloth, in sizes XS through 4X. For more exciting style news, follow me on Twitter at @NicoletteMason!
1. Boots $149.99, Clarks; clarksusa.com.
2. Clutch $825, Alexander Wang; (212) 977-9683.
3. Boots $635, Stuart Weitzman; stuartweitzman.com.
4. Cuff $317, Maria Francesca Pepe; wolfandbadger.com.
5. Shoes $149.99, Ivanka Trump; heels.com.
6. Coat (up to size 28), $109.95, Simply Be USA; simplybe.com.
Sunglasses $170, Ray-Ban at Sunglass Hut; (212) 759-3720.