Goodbye, Flats—Chic, Comfortable Kitten Heels Are My New Obsession
Three styles I'm loving.
I’ve lived a life resolute in the fact that high heels are simply not my ministry. Last year, I saw a TikTok video where André Leon Talley complimented a girl at Oxford for wearing flats—he made her sound like the most fashionable girl in the world, anchored largely by her choice of comfortable footwear. Naturally, it made me feel even more determined to never become a heels wearer.
But this winter, I've started to feel like my trusty loafers weren’t really cutting it for evening events. So, I've slowly started reaching for the kitten heels in my closet—they’ve become my favorite nighttime shoe.
Hailey Bieber co-signs the kitten heel while on a date with Justin Bieber.
As someone who’s 5'4", wishes they had legs a mile long, and loves to play with volume and proportion, I've found that pairing a kitten heel—always with a pointed toe—with a drapey pair of jeans is the closest I'll ever get to reaching higher planes. (Joking, but also, I'm serious.) The shape creates instant sharpness, and, with pants that run a touch long, the look feels elegant but a little undone. Being not too self-serious is always my style North Star.
Below, I’ve compiled a concise edit of pointed-toe kitten heels, should you be on a quest or are now inspired to search for the best ones out there. I've separated them into three distinct sub-categories: The Sock Boot, The Mule, and The Slingback. You don't need all three, but I find each worth it, so you'd never feel like they’re taking up space in your closet.
Sock Boot Kitten Heels
Sock boots give you that Lara Croft, ’90s-spy-meets-CBK energy. They’re usually monochromatic and work to streamline any outfit. I like to wear them when I have something more fun or daring happening up top, be it an argyle sweater from Khaite or an oversized mod-inspired Toteme check blazer.
The Row's Liisa Boots are an instant classic. I love the black suede—a great way to add texture to your outfit while still keeping things monochrome
I own and love Toteme’s Sock Boots. I have them in black, but have always been tempted to buy them in brown, as I think they’d look great with a classic blue jean, which my favorite way to style them!
I absolutely love how these Jacquemus boots look like if a grandma heel and a sock boot had a baby. I want to wear them with a string of pearls and an extra starchy light pink button-down from Phoebe Philo, stat!
Mule Kitten Heels
In my opinion, mules are the most elegant version of kitten heels. They’re what I’d wear if I could go for tea with Lee Radziwill (my forever muse). I like one that’s fun and a bit out-there to bring a simpler outfit to life. They work especially well with a cropped kickflare pant, and are maybe the best choice if you’re going from day to night. To me, a sexy kitten heel mule starts and ends with Manolo Blahnik.
I’d wear these cheetah heels with a wide-leg black jean and a fun going-out top for drinks with the girls on a Friday night.
These are classic, but have a trend-forward spin thanks to the snakeprint. They feel very Samantha Jones-coded.
My favorite thing about Manolo mules is that you can find the coolest vintage pairs on the secondhand market for such a great price. I’m obsessed with this velvet embellished pair for under $300. Texture and old-world charm—a major win!
Slingback Kitten Heels
Slingbacks are not only a dream to walk in, but they also offer an opportunity to get really fun. I tend to wear mine with a drapey jean and my white button-down from The Row. The more playful, the better!
I own these Proenza Schouler Dome heels, and they might be the greatest pair of slingbacks ever made. They’re architectural and sculptural and pure fun while also being serious enough to go with every outfit. I can’t recommend them enough.
If you’re looking for a plain black pair of slingbacks, look no further than these ones by Saint Laurent. You can style them my way (with a baggy jean or trouser), or go with a midi pencil skirt if you’re going for more of a Mad Men office siren vibe. (I envy you!)
Other Kitten Heels I Love
