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.
Hello, half-off sale.
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.
These are genuinely dreamy.
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:
The buckles only add to the allure.
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:
Showstoppers.
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.
The styling possibilities are truly endless.
I'll take any chance I get to pair a miniskirt with knee-high stiletto boots. There's no chicer combination.
Shop:
Consider me obsessed.
Sale prices like this don't come along every day.
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.
I won't eat or sleep until these are mine.
Gorgeous.
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.
This color is beyond chic.
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
-
Everyone in Paris Just Ditched Ankle Boots for This Boot Style That’s Way More ElegantAnd super sexy.
-
*Not* Suede Boots: The Rich-Looking Boot Trend Fashion People Everywhere Are Wearing With Jeans and Skirts for Fall 2025You'll want to add a pair to your rotation.
-
*Not* Ankle Boots—The Rich-Looking Shoe Trend That’s Quietly Taking Over for Fall 2025Shop the style inside.
-
Black Boots Are Fine, But *This* Fall Shoe Color Trend Looks Rich as HellLily James is a fan.
-
I Spent Over an Hour Browsing Nordstrom's New Arrivals—34 Standout Fall Finds I Can't Stop Thinking AboutYou'll want to see these.
-
Not Skinny, Not Wide-Leg—J.Lo Just Wore Ankle Boots With 2025's Most-Wanted Pant TrendCopy this fall outfit ASAP.
-
Cozy Cashmere! Sleek Suede! Dark Denim! 32 Affordable Fall Pieces You'd Find in a Wealthy Person's ClosetOh, did I mention they're under $250?
-
The Specific Way Everyone Stylish in NYC Will Be Wearing Boots With Jeans This FallIt's all about this styling trick.
