15 Trendy Plus Size Winter Skirt Outfits with Boots and Tights

Cold weather doesn’t mean you have to hide your favorite skirts. With the right mix of cozy layers, boots, and tights, you can stay warm while keeping your style on point. I’ve always loved how a good skirt outfit makes winter dressing feel fun and confident, even on chilly mornings.

When styled right, skirts work beautifully in winter. Pairing them with snug tights, tall boots, and soft sweaters creates a look that’s both comfortable and flattering. It’s all about balance, warmth, and adding your personal touch to make the outfit feel truly you.

Striped Knit Dress with Olive and Coral Accents

This fitted knit dress brings color and personality to cold-weather style. The mix of olive green, coral, and blue stripes creates a fun yet sophisticated look that stands out without trying too hard. With pointed heels and a clutch, it’s an ideal pick for work events or evening outings.

Burgundy Top with Brown Pleated Skirt

Rich, warm tones make this outfit feel perfect for the season. The soft burgundy top pairs beautifully with the earthy brown pleated skirt, giving a cozy yet stylish balance. Knee-high boots and a sleek handbag pull it all together for a confident, city-ready winter outfit.

Cozy Argyle Sweater with Leather Skirt

This look is perfect for chilly days when you want warmth with a bit of edge. The dark argyle sweater adds a soft and relaxed feel, while the leather skirt brings a bold touch that balances the outfit beautifully. Pair it with black tights and ankle boots for a stylish winter-ready vibe that feels effortless yet put together.

Check Mini Skirt with Black Sweater and Tights

This outfit blends classic charm with modern comfort. The check mini skirt pairs perfectly with the fitted black sweater, creating a flattering shape that feels confident and cozy. Black tights and chunky shoes finish the look with a touch of edge, making it great for evenings out or casual winter gatherings.

Houndstooth Skirt with Black Cardigan

The black cardigan paired with a houndstooth skirt creates a chic and balanced outfit that flatters every shape. The bold pattern of the skirt adds personality, while the solid top keeps things sleek and simple. With knee-high boots and tights, this look easily becomes a winter favorite.

Monochrome Plaid Skirt with Black Top

If you love clean and coordinated looks, this one is for you. The fitted black top pairs beautifully with the flared plaid skirt, creating a soft yet confident silhouette. Style it with heeled boots and minimal accessories for a polished winter outfit that works day or night.

Grey Turtleneck with Black Skirt

This outfit is all about quiet elegance and comfort. The grey turtleneck feels soft and cozy, while the fitted black skirt adds structure and a touch of sophistication. Wear it with warm tights and sleek boots for a simple look that still feels classy and modern.

Emerald Pleated Skirt with White Tank

This look feels fresh and easy, perfect for mild winter days or layering with a cozy jacket. The deep green pleated skirt adds movement and elegance, while the white tank keeps it casual and relaxed. Pair it with sneakers for a laid-back vibe or switch to boots and a cardigan for a warmer touch.

All Black Leather Mini with Turtleneck

An all-black outfit always feels powerful and sleek. The shiny leather mini skirt paired with a soft black turtleneck creates a balanced mix of bold and cozy. Add knee-high boots and a small handbag to complete a confident winter look that turns heads without trying too hard.

Navy Sweater with Metallic Pleated Skirt

This outfit feels cool, relaxed, and effortlessly chic. The loose navy sweater pairs beautifully with the metallic blue pleated skirt, adding a soft shine and flow to the look. White sneakers keep it casual and modern, while the silver crossbody bag ties it all together for a stylish winter day out.

Leopard Print Midi with Black Crop Top

The leopard print midi skirt adds instant personality and flair to any outfit. With a fitted black crop top, the look feels both playful and confident. Style it with sneakers for casual comfort or layer it with a jacket and boots when the temperature drops.

Charcoal Midi Skirt with Fitted Black Top

This outfit is a perfect mix of simplicity and grace. The charcoal midi skirt flows softly while the fitted black top keeps the shape clean and flattering. Add pointed flats or ankle boots for an easy, polished look that works for any day of the week.

Green Knit Sweater with Sparkling Midi Skirt

This look is bold and full of personality. The chunky green knit sweater feels warm and relaxed, while the shimmering skirt adds movement and a festive touch. Paired with heels and a small black bag, it’s a great mix of comfort and glam for winter parties or dinners out.

Tweed Mini Skirt Suit with Knee-High Boots

Nothing says winter chic like a classic tweed mini skirt paired with a matching jacket. The soft texture and light blue tones bring sophistication, while the black top and boots tie everything together. It’s the perfect outfit for workdays, events, or any moment when you want to feel both warm and stylish.

Classic Plaid Skirt with Deep Burgundy Cardigan

A plaid skirt never goes out of style, especially when paired with a cozy cardigan in a rich tone like burgundy. This combination feels warm and timeless, ideal for casual outings or coffee dates. Add opaque tights and lace-up boots to finish the look with a hint of vintage charm.