This Is the Only Boot Trend I'm Eyeing, Buying, and Shopping for In 2023
What can I say? I have a thing for shoes. Strappy sandals, ballet flats, wedges—name a style and I'll show you half a dozen pairs sitting in my closet. But perhaps for the first time in my life, I'm not juggling a handful of different footwear options this year. Instead, my sights are set on just one style that has taken up every inch of free space in my brain since 2023 began: stiletto boots.
To me, a tall heel, a pointed toe, and a fitted sock-like shaft make for the perfect shoe, not just for one season but all four. The '90s-inspired silhouette has taken over the fashion world, with brands like The Row, Diesel, and Manolo Blahnik offering hyper-elevated options while more affordable options like Porte & Paire, Reformation, and Schutz are selling chic alternatives that won't break the bank. Scroll down to shop for a pair of your own. This is one purchase you won't regret, trust me.
Whenever I have no idea what to wear, I usually put on some variation of this look. Basically, it has to be all black and feature a great pair of stiletto boots and a leather jacket.
Shop:
It's almost impossible to find boots this good under $100, let alone under $70.
I've had my eye on these for months and have tried them on in two separate cities. Now, I finally feel like I'm ready to go for it.
There's no outfit combination I love more than a tiny dress, sheer tights, and extra-pointy boots. It's so elevated and chic but also impossibly sexy.
Shop:
I never would have said I wanted sock boots two years ago, but here I am now, buying as many pairs as I can find.
If you want to splurge on a pair you know will last forever, go with one from Stuart Weitzman.
Unsure how to style this type of boot? Google or search Pinterest for something like "'90s stiletto boots," and you'll find thousands of iconic images.
Shop:
I love that you can wear these under jeans without any of the bulk that comes with most mid-calf and knee-high boots.
Hello, the Met? I'd like to submit a work of art. Thanks!
One way to make your boots the star of your outfit is to pair them with fishnet tights with a skirt with a slit. They only peak out a bit when you walk but instantly turn up the wow factor of any look.
Shop:
If you haven't shopped from Porte & Paire yet, here's your sign to do so. The brand makes high-quality, on-trend footwear at a price that stands out among Net-a-Porter's usual selection.
I'll take any chance I get to pair a miniskirt with knee-high stiletto boots. There's no chicer combination.
Shop:
These give strong '90s Jen Aniston vibes, and I'm 100% here for it.
I live by this sartorial mantra and this sartorial mantra only: The sharper the toe, the chicer the boots.
Shop:
I'm genuinely shocked that these are in stock at Saks. They're sold out everywhere else.
If black leather boots aren't doing it for you anymore, now's the perfect opportunity to branch out and try a different material or color. Dare I suggest a mock croc or a taupe suede?
Shop:
When I want a high-quality pair of shoes, I always go to Dear Frances. The brand has never wronged me—ever.
You've made it to the end—congratulations! Now collect your prize, aka these Larroudé boots.
Next up: You're In, You're Out: 7 Dated Boot Trends That Didn't Make the Cut In 2023
Eliza Huber is an NYC-based senior fashion editor who specializes in trend reporting, brand discovery, and the intersection of sports and fashion. She joined Who What Wear in 2021 from Refinery29, the job she took after graduating with a business degree from the University of Iowa. She's launched two columns, Let's Get a Room and Ways to Wear; profiled Dakota Fanning, Diane Kruger, Katie Holmes, Gracie Abrams, and Sabrina Carpenter; and reported on everything from the relationship between Formula One and fashion to the top runway trends each season. Eliza lives on the Upper West Side and spends her free time researching F1 fashion imagery for her side Instagram accounts @thepinnacleoffashion and @f1paddockfits, watching WNBA games, and scouring The RealReal for discounted Prada.
-
Brace Yourself: 2025's Most Divisive Shoe Trend Has Arrived
You'll either love it or hate it.
By Anna LaPlaca
-
I Know You're Stylish If You Tuck Your Jeans Into Boots Like These 5 Chic Women
Don't be scared.
By Nikki Chwatt
-
J.Lo Just Ditched Her Skinny Jeans to Wear This 2025 Denim Trend With $170 Uggs
Casual yet chic.
By Nikki Chwatt
-
New Yorkers Will Wear This Celeb-Concocted Ankle-Boot Outfit for the Next 3 Months
Sydney Sweeney just modeled it for us.
By Allyson Payer
-
Basic Black Leather Boots Will Never Be Out, But This Trendier Alt Is Officially In for 2025
So chic.
By Nikki Chwatt
-
Unlock the Secret to a Chic and Elegant Winter Wardrobe With These 6 Key Pieces
From timeless coats to expensive-looking sneakers.
By Jennifer Camp Forbes
-
Hailey and Kendall Just Wore the "Dated" Shoe Trend New Yorkers Actually Wear All the Time
I need a pair ASAP.
By Nikki Chwatt
-
No Offense to Sneakers, But These Boots Are a Far Chicer Match for Leggings
The elegant choice.
By Eliza Huber