When friends ask me which trends to have on their radar this season, I’ve noticed that lately the first style to roll off my tongue is the pencil skirt. After several years out of our rotations, the sleek, form-fitting silhouette has made a triumphant return to the runway and at once worked its way into the rotations of the chicest celebrities, too.
As I’ve been admiring this resurgence, I’ve also been paying close attention to the shoe pairing that the fashion set is using to complete their looks. Because, let’s be honest, despite its polish, the pencil skirt isn’t always the easiest piece to pair with footwear.
After some dedicated research, I’ve landed on two shoe styles that consistently flatter every kind of pencil skirt. Both tried and tested by some of the chicest dressers around, these are the pairs I’d recommend wearing with your pencil skirts this winter—and well beyond.
1. Ballet Flats
I’ll admit, I once thought that pairing ballet flats with a pencil skirt risked cutting the legs short. But recently, I’ve seen too many effortless, elegant examples to keep believing that.
Take Alexa Chung, for instance. Styling a knee-grazing leather pencil skirt with a graphic T-shirt and classic black leather ballet flats, she made the sharp silhouette feel relaxed yet refined. The flats added an easy, wearable edge to her look without compromising on sophistication.
Kaia Gerber has also leaned into this combination, opting for a minimalist pencil skirt and a pair of low-heeled ballerinas. Poised, elegant and understated, this is a two-piece look you can keep coming back to.
2. Pointed-Toe Heels:
If your goal is to embrace the pencil skirt’s innate elegance, there’s no better partner than a pointed-toe heel. Sleek and sculptural, it elongates the leg and complements the skirt’s tailored shape perfectly.
This season, I’ve spotted countless celebrities leaning into this timeless pairing. From calf-grazing pencil skirts to knee-length iterations, the pointed heel brings a touch of refinement to every version. Elsa Hosk and Hailey Bieber both crafted impossibly chic looks around this classic combination.
With these two shoe styles in rotation, my pencil skirts are about to get much more airtime. Scroll on to discover the chicest ballet flats and pointed-toe heels to style your pencil skirts with this season.
Shop Ballet Flats:
Be quick! These are new-in and already showing signs of selling out.
The khaki colour trend is on the rise this winter, and these elegant ballerinas are an easy way to jump on the trend.
Style these with white socks to give your look a preppy feel.
The chocolate brown colour trend isn't showing any signs of slowing down.
While I love these in the classic black, they also come in a fresh shade of ecru.
Reformation's Bethany Ballet Flats are a fashion person's favourites for a reason.
Shop Pointed Toe Heels:
Honestly, these look so much more expensive than they actually are.
The slingback detailing adds a sleek point of interest, as well as light support.
While I love these in the classic black, they also come in a fresh shade of cream.
Every great wardrobe starts with a classic pair of black heels.
The kitten heel adds a little height without sacrificing comfort.
Style these with semi-sheer tights and a pencil skirt all party season long.
-
H&M Just Dropped a $40 Version of The Row's Winter Flats I Keep Seeing on Chic New YorkersA sellout is imminent.
-
My Sister Asked Me What She Should Buy From Amazon—30 Fashionable Items I SuggestedBasically, everything on my Black Friday wish list.
-
If You're Going to Keep Wearing Floral Dresses in the Winter, This Jacket and These Boots Are Absolutely CrucialIt's the only practical (and chic) way.
-
Don't Write Off Skinny Pants Until You've Seen How Elsa Hosk Just Styled ThemThey look thoroughly modern.
-
From Pilates in L.A. to Meetings in Paris, Kendall Jenner Can't Stop Wearing These Classic Designer FlatsI don't blame her—they look sleek and so comfortable.
-
Want to Wear Dark-Wash Jeans the 2025 Way? Style Them Exclusively With This Rich Color TrendThe chicest shade pairing for fall.
-
As Far as I'm Concerned, This Is the Only Fashion-With-a-Capital-F Halloween CostumeThis Aritzia dress is very Princess Diana.
-
Not a Bomber, Not a Trench: Everyone With Taste Is on the Hunt for This "Dated" Leather Jacket TrendI just ordered one from Revolve.
