8 Sweater and Skirt Outfits

A sweater and skirt outfit is one of those winter and fall combinations that seems simple on the surface but can be a little tricky to pull off. You’ve pulled your favorite sweater and skirt, but then the questions arise: Is the sweater too oversized? Do I look boxy? Are the proportions off? What shoes do I wear with a sweater and skirt?

When done right, a sweater with a skirt is the epitome of comfy chic. It’s one of my favorite fall outfits, but if you’re new to the pairing, it can feel intimidating. Luckily, you only need a couple of tips and a willingness to do some trial and error until the outfit feels just right to nail this combination.

Below, I have a great oversized sweater and skirt outfit that you can wear as shown in fall and with an extra layer in winter. I’m also sharing dos and don’ts for how to wear a sweater with a skirt to guide you as you build your own look!

Natalie Yerger wearing AllSaints sweater CeFinn wool skirt Steve Madden knee high boots and Mansur Gavriel lady bag
woman wearing oversized sweater and skirt outfit with black knee high boots

Outfit Details: AllSaints Black Sweater, CeFinn Wool Skirt (old, similar here and here), Steve Madden Boots (old, similar here)

How to Wear a Sweater with a Skirt

  • For a tucked-in look, choose a skirt that sits at the natural waist (rather than at the hips). A skirt that has enough stretch or an elastic waistband to accommodate tucking and enough structure to smooth out any extra fabric from the sweater is ideal.
  • If you live in a warm climate or you want to showcase your shape, try something lightweight and fitted, like sleeveless sweater or even a bodysuit in a knit, sweater-like material.
  • When planning to wear the sweater untucked, avoid sweaters that are boxy or oversized. Instead, try reaching for a cropped sweater or a knit that cinches at the waist. Alternatively, choose a looser knit that has feminine, elongating details (like side slits). 
  • Nailing this look is all about proportions, so play with various skirt lengths, shoe types, and sweater cuts until it feels just right.
  • If things are looking chunky or bulky, add a belt to create a waist. For the tucked-in look, place the belt at the top of the skirt. For the untucked look, place the belt over the sweater at the smallest part of your waist.
  • If you’re new to styling sweaters with skirts, a tuckable sweater, midi length skirt, and knee high boots is the most easy-to-put-together combination. Once you’ve nailed this, move on to styling mini skirts with knits and calf or knee-length skirts with knits.

More Sweater and Skirt Outfit Ideas

1. Maxi Skirt with Sweater, Blazer, and White Booties

maxi skirt with oversized white sweater and white blazer

Image via Kat Jamieson

2. Cropped Cable Knit Cardigan with a Maxi Skirt

cardigan with maxi skirt outfit

3. Black Leather Jacket over a Knee-Length Midi with a Long Sleeve Sweater

fall skirt outfit with sweater and black leather jacket

Image via Fashion Jackson

4. Mini Leather Skirt with Over-the-Knee Boots and a Turtleneck

mini skirt and sweater outfit with over the knee boots

5. Side-Slit Sweater with Midi Satin Skirt and Ankle Boots

Jenni Kayne sweater styled over a slip skirt with ankle boots

Image via Jenni Kayne

6. Untucked Tunic Sweater with a Pleated Skirt and Knee High Boots

woman wearing gray oversized sweater with black belt knee high boots and black pleated skirt

Image via Mango

7. Turtleneck Sweater with Tiered Midi, a Belt, and Heels

holiday party sweater and skirt outfit with high heels sand belt

Image via Banana Republic

8. Oversized Sweater Outfit with Skirt and Knee-High Boots

Natalie Yerger wearing fall outfit with black sweater and green wool skirt


Keep scrolling for a selection of my favorite midi skirts, pencil skirts, long skirts, and knit skirts to try with your sweaters this fall. If you’re in need of new knitwear, check out my post on the best sweaters for women, which features turtleneck sweaters, pullovers, cropped sweaters, cardigans, and v neck sweaters, to complete the combo.

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