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

Last night, instead of reaching for my sleeping pill, I used the Zappos app to calm the brain. It worked brilliantly! And while scrolling through an endless number of shoes, I started to develop a strong feeling towards high boots… and felt inspired to write.

Let’s break the topic down into heeled high boots and flat high boots.  The latter will come in another post.

So here’s the thing with high boots (that are heeled). They’ve been on the fashion scene forever, and I know a lot of women who count them as absolute essentials. That said, there’s a fine line between looking chic  and polished, and looking hooker.

While black boots may seem to all look the same, that’s not the case. There are subtle differences to look out for when seeking out the most flattering and elegant of the bunch. I’ve broken down heeled boots into my two favorite sub-categories: the 70s structured style and the sleek ‘n’ sexy (but not slutty).

loeffler randall boots from zappos dolce vita boots from piperlime

The structured 70s style tends to look more retro, with a stiffer shaft and chunkier heel.

Kate Spade wedge bootsvia spiga boots from nordstrom

The sleeker types offer a very slim, fitted shaft that contours to the ankle and calf, and a thin, stiletto style heel, or sometimes a skinny wedge.

In both cases, there are some pitfalls to avoid in order to remain on that chic and polished side of the fence:

1. Make sure the boot fits you at the top! This means the top of the boot should hit below the knee. If a boot hits you at the knee-cap (or above) it is too big. Furthermore, the top should fit snugly or semi-snugly around your leg. For 70s styles, it will not be as snug due to the design, but it should never ever resemble a moat around your leg.

2. Avoid boots that unintentionally bag or slouch near the ankle. This looks messy. Of course, with most leather or leather-like boots, some pouching will occur, but with a good boot, it should be minimal.

3. Not everyone can pair with a shorter skirt. Some can, but this is not the norm. If you can rock it, do it. Just remember to wear opaque tights. As an alternative, try a knee-grazing pencil or swing skirt.

4. If you’re gonna do them with jeans, make sure those jeans (or leggings) are FITTED AT THE KNEE AND CALF. Otherwise, you’ll get all sorts of sloppiness coming out of the top of the boot. And if you’re going the pants/boots route, think about adding some volume to your top half to balance out the severely streamlined feel of the jeans/boots. This means a chunky sweater, or a longer blazer.

Stay tuned for part 2, where we’ll tackle the weird world of flat boots. It’s gonna be awesome.


These chunky retro style beauties from Elizabeth and James are currently on sale at Gilt. Happy early xmas, all. 


[tweetmeme] One Response to Here’s the thing with high black boots (part one)
  1. Cobly
    September 5, 2013 | 7:16 am

    I have a hard time getting boots too. I finally found some at a company called Wideshaftboot!!

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