Here are some comfortable outfits for those who enjoy wearing skirts in colder weather. Some of the looks are for those who experience milder winters. Also, editorials don’t always show how to layer up and stay warm in an outfit. Use these looks as a base and add items like hosiery, HEATTECH undies, coats, puffer jackets, scarves, and headgear for insulation. 

Some of the outfits are dressier than others. Choose a colour palette that works for you.

1. Relaxed Casual Flare

Combine a casual patterned flared midi skirt with a fluid pullover that picks up a colour in the pattern. Semi-tuck the pullover, or leave it out. A short cardigan that’s buttoned all the way through works well as a pullover too. Add casual flat booties or tall boots. Feel free to add fun visible socks that are in the same palette to the short boots option. Pop an easy coat, jacket or coatigan over the top. Here I particularly like the addition of the slate grey boots, pattern mixed scarf, and crossbody bag.

Seasalt Lysbeth Coat

2. Sassy Black Sandwich

Sandwiching an outfit together with black top and footwear is an effective styling strategy for most solid skirts. Pick any colour and “sandwich” it with black. It also works well when there is a black component in the pattern of the skirt. Here, the electric blue is marvelous with the black support act and black hair of the model. Try sandwiching with navy, grey, white, tan and shades of brown if black is not your thing. I see sheer black hosiery and taller black boots too.

Eloquii Velvet Column Skirt

3. Plaid, Tights and Sneakers

Shorter checked and plaid Winter skirts in straight and A-line silhouettes are a classic. My petite clients and friends wear them particularly well. They are often worn with black opaque tights, boots, and pullover, which is a slam dunk (more black sandwiching.) But here, I like the addition of the rusty red opaques and black sneakers to change things up. Hi-tops are another option, or wear boots. Matching the colour of the opaques with a top is another way to go.

Uniqlo Wool Blend Mini Skirt

4. Cosy Sequins

Create a fun juxtaposition by combining a dressy sequin skirt with a cosy and roomy pullover. A pullover with a high-low hemline tends to add a little structure. Finish off the look with dressy and tailored footwear that works with the palette. Choose another type of dressy skirt if sequins aren’t your thing. Add jewellery, watch and eyewear as desired.

Whistles Sequin Midi Skirt