Is It Worth Investing in the Perfect Winter Boot?

I was on set for a photo shoot last week and couldn’t seem to stop staring at the ground. I wasn’t looking at the carpet, or the floorboards, or the metaphorical pit of my emotional well-being. I was looking at a pair of boots — off-white, slip-on, chunky-soled — borne to and fro on the feet of Preia Narendra, Miu Miu’s inimitably chic SVP of Marketing and Communications.

“Those boots,” I finally managed to croak out in the midst of my trance. “What are they?”

“Oh, these?” she said, gesturing down at the object of my most significant surprise crush since The Handmaid’s Tale‘s Max Minghella. “They’re 3.1 Phillip Lim.”

I made a mental note that refused to be filed away.

I returned to the office, but my mind stayed behind with the boots. They were more than just aesthetically pleasing. They were proof that December’s most challenging style question (do shoes that are both “cool” to look at AND practical to wear around in 30-degree weather with possibly icy or snowy conditions exist!?) had a resoundingly affirmative answer. I could tell the moment I saw them that not only would I want to wear these shoes with every outfit all winter long by virtue of their encapsulation of style, but I also could wear them with every outfit all winter long by virtue of their utilitarian nature. In that sense, I felt as if I had discovered buried treasure, or the secret to life. Or both.

Given my professional familiarity with the tiers of designer pricing for leather boots, their cost ($550) didn’t surprise me when I looked them up online. It did, however, trigger a spiral of cost-per-wear mental math that resulted in equal parts exasperation and hope. Rats!

Nonetheless, I felt called to prove my hunch that they might be the Holy Grail of winter boots by test-driving a sample — if not for me and my size-9 feet, then at least for the sake of someone else with size 5, 6 or 11 feet (those are the sizes left in the “Vanilla” color that won over my heart, although I will note all sizes are left in “Black”). So I called in a slightly-too-small loaner pair and gave them a whirl in conjunction with the rest of my wardrobe. When they arrived at my desk, I traced a gentle finger across them and sighed inwardly at the feeling of what was admittedly very nice leather. I was almost hoping that my mission would be difficult — that I would find myself unable to conjure up a single outfit to go with the boots — but alas, when I got home, it was just as I expected. Wearing them was easier than apple pie. It was more seamless than a tube top. It was a state of higher existence, one in which getting dressed for winter was delightful instead of the conceivable plot for a psychological thriller. Such is the power of a shoe that somehow goes with all your pants.

If you’re in the market for an investment boot that is both functional for winter and fun to look at for always, I can very comfortably recommend this one. If you’re interested in a less expensive alternative, I think this $64 pair from Urban Outfitters might do the trick, and there are some others to peruse in a shopping bar below. But also! If you already have a pair of go-to winter boots that reliably scratch your style itch and effectively shield your toes from the elements, I oh-so-fondly beg you share it in the comments.

Photos by Edith Young.

Harling Ross

Harling is a writer and was most recently the Brand Director at Man Repeller.

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