Skirts and boots are one of winter's best outfit combinations. The pairing is feminine, practical, and surprisingly warm when you layer it right.
The secret is choosing the right boot style for your skirt length and occasion. Get it right, and you've got an outfit that looks intentional and stylish without much effort.
Here's how to wear skirts with boots this winter, from the best boot styles to the skirt lengths that work.
The best boots to wear with winter skirts
Not all boots work equally well with skirts, so here's what tends to look best.
Knee high boots
Knee high boots are brilliant with skirts because they provide warmth and coverage while creating a sleek, elongated silhouette. They work particularly well with midi and mini skirts, filling that gap between hemline and boot top beautifully.
- Pair with A-line or pencil skirts for a polished look
- Add thick tights for warmth
- Make sure there’s not too much bare leg (or tight) showing between the skirt and boot – this can look a bit unfinished in winter
shoezone pick: Lilley Womens Tan Knee High Boot
Ankle boots
Ankle boots are the most versatile option and work with pretty much every skirt length. They're great for when you want the coverage of boots but don't want the commitment of knee highs, and they're easy to walk in for all-day wear.
- Try them with midi skirts for a relaxed, contemporary look
- Pair with mini skirts and thick tights for something a bit more playful
- Heeled ankle boots dress things up, while flat styles keep it casual and comfortable
shoezone pick: Lilley Womens Black Ankle Boot
Biker or chunky boots
For an edgier vibe, biker boots or chunky boots add instant attitude to winter skirts. They're particularly good at balancing out more feminine skirt styles like florals or pleats, creating that high-low mix that always looks current.
- Pair with denim skirts for a casual weekend look
- Team with flowy mid skirts to add weight and structure
- The chunkier the boot, the more streamlined you want to keep your top half to avoid looking too heavy overall
shoezone pick: Lilley Womens Black Studded Calf Boot
Brown and tan boots
Brown boots and tan boots soften the look of winter skirts and work beautifully with warm, autumnal colours. They're less harsh than black and create a more approachable, relaxed vibe that's perfect for daytime wear.
- Try tan boots with denim or corduroy skirts
- Pair brown boots with neutral knits and earth toned skirts
- Wear with midi-length skirts to create a tonal, sophisticated look that feels very now
shoezone pick: Lilley Womens Tan Chelsea Pull On Boot
Chelsea boots
Chelsea boots are sleek, smart, and incredibly easy to style with skirts. They're brilliant for when you want something polished but not too formal, and they work for both work and weekend wear.
- Pair them with A-line or pleated skirts for a preppy, put-together look
- Try with leather or suede skirts for something more contemporary
- Chelsea boots in black or brown are the most versatile, but don’t be afraid of trying other colours if you want something different
shoezone pick: Lilley Womens Black Chelsea Boot
Types of winter skirts to wear with boots
Maxi skirts
Maxi skirts with boots create a bohemian, slightly unexpected look that's great for when you want to stand out a bit. The key is choosing boots that peek out from under the hemline, like ankle boots or low Chelsea boots, so you get that layered effect.
- Pair with chunky knits and longline cardigans for a cosy, textured outfit that’s perfect for relaxed weekends
- Maxi skirts work best with flat or low-heeled boots to keep the proportions balanced and avoid looking too bottom-heavy
Midi skirts
Midi skirts are arguably the most flattering length to wear with boots because they work with almost every boot style. The hemline hits at the perfect spot to pair with ankle boots, knee highs, or anything in between.
- Try with ankle boots for work, or A-line midis with knee high boots for something dressier
- Denim midi skirts with chunky boots create a brilliant casual look that’s effortlessly cool without trying too hard
Mini skirts
Mini skirts with boots can look brilliant when styled right, but they do need a bit more thought in winter. The trick is balancing the shorter hemline with coverage elsewhere, like thick tights and a longer coat.
- Pair mini skirts with knee high boots to minimise bare leg on show, or try with chunky ankle boots and tights for a more casual vibe
- Add an oversized jumper or blazer to keep proportions balanced and avoid the outfits looking too bare on top
How to wear winter ankle boots with skirts
Ankle boots are the easiest boot style to wear with skirts because they're so versatile.
Here's how to get the most out of them this winter:
Consider the gap
The golden rule is to think about the gap between the ankle boot and the skirt. With midi skirts, this gap is minimal and looks naturally polished. With mini skirts, you'll have more of your leg on show, so make sure you're wearing good quality tights that are thick enough for winter.
Play around with heel heights and styles
Choose heeled ankle boots for a dressier look that's great for work or evenings out. Flat ankle boots keep things casual and comfortable for everyday wear. Chelsea-style ankle boots add a sleek, contemporary edge, while chunkier styles create a more relaxed, fashion-forward vibe.
Tuck, belt, and layer
Tuck skirts in slightly at the waist to define your shape, and add a belt if your skirt is quite loose. Layer with fitted jumpers or tucked-in shirts to keep your silhouette streamlined, especially if you're wearing chunkier ankle boots that add volume at the bottom.
5 winter skirts with boots outfit ideas
Denim midi and chunky ankle boots
A denim midi skirt with chunky ankle boots creates that perfect casual-cool vibe for weekends. Add a chunky knit jumper and a longline coat, and you've got an outfit that works for coffee runs, shopping trips, or days out with the kids. Keep it relaxed with a crossbody bag and minimal jewellery.
Pleated midi and knee high boots
For work or smarter occasions, pair a pleated midi skirt (in black, navy, or neutral tones) with sleek knee high boots. Add a fitted roll-neck or tucked-in blouse, and layer with a tailored blazer or wool coat. This combination is polished, professional, and surprisingly comfortable for all-day wear.
Mini skirt and over-the-knee boots
When you want to make a statement on an evening out, try a mini skirt (leather, suede, or heavy fabric) with over-the-knee or tall knee high boots. The boots provide warmth and coverage while keeping the look sleek. Add a fitted jumper or bodysuit and a leather jacket for edge.
Corduroy a-line and brown Chelsea boots
Corduroy skirts scream cosy autumn-winter vibes. Pair an A-line corduroy skirt with brown Chelsea boots, a tucked-in turtleneck, and a chunky cardigan. This outfit is perfect for relaxed weekends and has that effortlessly stylish quality that always looks intentional.
Maxi skirt and flat ankle boots
For a bohemian winter look, style a knitted or wool maxi skirt with flat ankle boots peeking out from underneath. Layer with an oversized jumper, long coat, and chunky scarf. This combination is brilliantly warm and works perfectly for days when comfort is your absolute priority.
Tips for keeping warm when wearing winter skirts with boots
Skirts and boots can absolutely work for winter, but you do need to layer smartly to stay warm:
- Invest in good quality tights: Thick opaque tights (60 denier or higher) make all the difference. Thermal tights or fleece-lined versions are brilliant for very cold days
- Layer underneath: Don't be afraid to wear thermal leggings under your skirt if it's freezing. No one will know, and you'll actually be warm enough to enjoy your outfit
- Choose longer skirt lengths: Midi and maxi skirts naturally provide more coverage than minis, making them warmer and more practical for winter
- Add knee high boots: They cover more leg than ankle boots, providing extra warmth and reducing the amount of tight exposed to the elements
- Layer on top: Long coats, oversized cardigans, and chunky scarves add warmth without ruining the silhouette of your skirt-and-boots combo
- Pick the right fabrics: Wool, corduroy, and heavier cotton skirts are warmer than lightweight or floaty materials. Save the thin fabrics for spring
Final thoughts
Skirts and boots are a winter styling combination that's both practical and stylish. With the right boot choice and a bit of smart layering, you can wear skirts all winter without freezing or sacrificing style.
Explore shoezone's collection of women's winter boots to find the perfect pair for your winter skirt wardrobe.
Check out the shoezone blog for more style tips and footwear suggestions for every occasion.