At the beginning of August, I shared 6 Timeless Shoe Brands I Keep Coming Back To Every Summer. For Part 2, I wanted to shift the focus slightly. We’re reaching that point in the season where I still see plenty of open shoes on the streets of New York, from sandals and flip-flops to ballet flats, but I’m also personally starting to think about the loafers and closed-toe styles that will carry me into early fall.
As always, I’m looking beyond whether a shoe simply looks chic, that’s only one part of what makes a good shoe. Besides thoughtful design, I want quality materials, good craftsmanship and, most importantly, something I can actually walk in. The best shoes should become easier and more beautiful with wear, not something you dread putting on and suffer through all day.
And because I never think it’s helpful to shop without first considering what you actually need, here’s the framework I use when thinking about a well-rounded transitional shoe wardrobe.

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