Here’s the thing with high black boots (part two)

Following up on the heeled high boot talk I started a little while ago, let’s discuss what to look for when seeking out a flat high boot.

Flat boots can be taken through February, March, and even into April/early May, depending on your weather situation. I strongly (strongly!) suggest you do not go the boots/bare legs route, as I have seen it happen and it’s not pretty. Flat boots are most successful when paired with slim jeans or leggings-style pants. You can do them with a skirt, but unlike heeled boots, not every skirt or dress will work. Pencil skirts, sheath dresses, and more fitted work-like wear is best paired with a bit of a heel. More casual, fluid skirts can work with a flat boot.

And if you choose a timeless style, they will be your best friend every fall and winter for years to come! A super solid investment.

As I mentioned with heeled boots, fit is king. The boots should FIT YOU. This may sound like a duh, but it’s a point that people tend to overlook way too often. Make sure the calf is neither too tight nor too loose. It should be form-fitting without cutting off circulation. And keep the ankle slouching to a minimum.

Here are a few of my faves:

tory burch black riding boots

Tory Burch does a great riding style boot. When going the riding route, think minimal detail. Too many bells, whistles, buckles, and straps will make the boot look busy and cheap. And nobody wants to look busy and cheap.


For something a little more laid back, look to Madewell. These boots offer a hint of western style while remaining cool and relaxed.

corso como boots

And for those purists out there, I love the simplicity of Corso Como‘s boot. It’s simple but not boring. Clean, structured, and expensive-looking (without being so).


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