What Do Your Dream Boots Look Like?


I have successfully resisted knee-high boots for years. I rode out the last cycle when they were in fashion, about 15 years ago, when everybody was tucking their skinny jeans into them. I knew that look wasn’t for me.

In the last months, though, I’ve wanted something to wear under skirts or dresses that wasn’t tights. So I caught what I’ve been calling “tall-boot fever.” I would never wish this sickness on anyone.

I set off on a Goldilocks-style journey to find just the right pair.

There are styling challenges. I have longish legs and hate when boots hit at the widest part of my calf. Boots also tend to be cut offensively narrow. I like that Vince is offering wide-calf boots and am disappointed, although never surprised, that more designers aren’t following suit.

My friend Krissy has a pair of kitten-heel Manolo Blahniks that she got from the RealReal for less than $200. She relayed the following when I texted her about them: “Manolo studied how heels affect hormones and knows the exact wave of the vagina in orgasm and mimicked that with the wave of the shoe.” Is it science? Is it entirely apocryphal? Do I care if my boots could be literally orgasmic? (The answers to those questions are: probably not, could be and no way.)

I couldn’t find hers, and while I loved the Manolo Blahnik Ocularas, the heels were too high. So were the Kinsey 95s from Jimmy Choo. I wanted three inches, maximum. I can’t sustain walking or standing in anything higher than that.

The Remy from Reformation and the Cavallo from Bottega Veneta and the Boeri from Rachel Comey were too unstructured in the calf, closer to riding boots. I craved boots that showed some shape of my calf and ankle, but I didn’t want stretchy boots, either. Dries Van Noten has an array of tall patent leather boots, but patent leather looks too fetishy on me. (If anyone is looking for boots that skew a little kinky, please get them.)

At last I found my dream pair.

I really resisted buying these, but they checked every box: fitted, chunky heel in the right height. Also, I like the cool walnut-y shade of brown. They look like something Carolyn Bessette-Kennedy might have worn. I watched for weeks as they began to sell out online. Finally I knew what I had to do. Over Thanksgiving weekend, I sold a bunch of clothes and shoes on Instagram to finance them. Was that a deus ex machina, or was that me using a thriving secondhand market to my advantage? While you decide, I’ll be wearing them with a vintage Karl Lagerfeld-era Chloé dress. ($1,950)

These are a little slouchier than I wanted, but I love the short but interesting curved heel. The seam down the front and the squared-off toe look … well, expensive. I’d wear them with loose trousers, tucked in, and maybe a thick sweater and walk my dog feeling as if I really had my life together because that’s a pretty advanced look. ($1,280)

I have found that brands like Rossi, Manolo Blahnik and Jimmy Choo still do their tall boots that were hits the last time around. Sadly, if I wear anything that reads tough (leather jackets, anything with studs, most anything black), I look as if I’m in costume. These brown suede boots are soft (literally and figuratively and probably emotionally). If I saw a woman on the street wearing a black dress and coat with brown boots, I’d probably follow her around just to see what she was up to. ($1,695)

Classic almond toe, great stacked heel, interesting seams that don’t distract. If I were in the market for black knee-high boots, I would seriously consider these. Maybe with a jacquard pencil skirt? Or, for spring, with a full cotton skirt and a tucked-in shirt? “Classic” is such an overused word when writing about fashion, but it’s important to be able to wear something for years and years without it being dated. ($1,350)

I recently watched the documentary “Meet Me in the Bathroom,” about the New York music scene of the early aughts — the Strokes, Interpol, the Yeah Yeah Yeahs — and this pair looks like what a young woman with side-parted hair, a lot of eyeliner and a dress with either an empire or drop waist (waists were all over the place 20 years ago) would wear to one of those shows. I love the idea of wearing them with a prim tea-length dress for a little tension. ($725, now on sale for $435)



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