Hailey Bieber is my style muse, so I’ve been closely observing her fall outfits and bookmarking the looks I want to re-create. While I’ve noticed her wearing Gap’s dark-rinse baggy jeans, most of her outfits have featured non-denim pants like slim black trousers or pencil skirts—especially the latter. Recently, she has worn leather pencil skirts twice, pairing them with knee-high boots, similar to how chic dressers in London and Paris are styling them.
Pencil skirts and knee-high boots, especially heeled styles, are trending—and for good reason. This outfit combination offers a fresh and sophisticated alternative to jeans and boots. It’s also versatile, pairing well with casual tops like a classic sweater. Bieber showcased this look perfectly—a black crewneck sweater, black leather pencil skirt, and heeled knee-high black leather boots. Not only Bieber but also European fashion people are embracing this fall look, proving that if you’re tired of jeans and trousers and want to refresh your cold-weather wardrobe, a pencil skirt with knee-high boots is the refined choice. That said, keep scrolling to see how the style set is wearing this look and shop the pieces needed to re-create their elegant ensembles.
On Hailey Bieber: Gucci by Tom Ford vintage boots
Get the Look
Quince
100% Mongolian Cashmere Shrunken Crewneck Sweater
Nordstrom
Pima Cotton Blend Crewneck T-Shirt
If you don’t already own Nordstrom’s best-selling white tee, this is your sign to add it to your cart.
H&M
Midi Skirt
Style with knee-high boots or sheer tights and slingbacks.
Open Edit
Elara Pointed Toe Knee High Boots
Trust me—these will be your go-to shoes this fall and winter.
More Ways It Girls Are Styling Pencil Skirts and Boots
Style notes: The pop of red from the sweater and the luxurious shine from the patent-leather boots takes this pencil-skirt outfit to the next level.
Style notes: There’s so much to love about the styling here. The brown boots perfectly complement the white turtleneck and ivory skirt, and the slim black belt pulls everything together effortlessly.
Shop Pencil Skirts and Knee-High Boots
Good American
Matte Jersey Midi Pencil Skirt
Sorry if this offends anyone, but brown pencil skirts look more expensive than black ones.
Reformation
Dominique Knee Boots
Currently sitting at the top of my wish list.
MANGO
Faux-Leather Pencil Skirt
It’s been really tough to find an under-$100 faux-leather pencil skirt that doesn’t look inexpensive. So I’m thankful this one just arrived at Mango. It’s $90, looks rich, and is flattering.
H&M
Knee-High Boots
These are guaranteed to sell out by November 30.
ALL THE WAYS
Jane Midi Skirt
A black skirt like this one is a must-have in any It girl’s wardrobe.
Tony Bianco
Apollo Heeled Boots
These are for those who want extra height or simply love the alluring appeal of stilettos.
