5 Winter Skirt Trends Everyone Is Pairing With Boots This Year
I typically wear pants almost all year long, but this winter I’m stepping outside of my comfort zone by exploring skirt trends that I can pair with my usual boots and sweaters. Skirts are versatile pieces that can easily fit into your wardrobe, even in freezing temperatures. I've observed stylish New Yorkers confidently wearing a range of skirt trends in chic looks. After browsing Instagram and Pinterest for outfit ideas, I noticed that certain skirt styles kept appearing. Fashion enthusiasts in NYC have taken a liking to leather skirts and other styles such as midi and, more recently, low-rise skirts. One commonality among these trends is their timeless silhouettes, offering simplicity that’s easy to style in multiple fashionable ways. The days of feeling frumpy in winter are over for me; I’m opting for more stylish outfit choices, and these skirt trends fit the bill. Classic shapes like knee-length and pleated skirts are being rediscovered by the Instagram fashion community, turning them into the next big winter trends, which I find very exciting. If you’re looking for new bottoms to pair with your boots, keep reading to explore these timeless winter skirt trends.
**Leather Skirts**
- **Betty Faux Leather Maxi Skirt**: A rich deep blue combined with leather is a perfect match.
- **Leather Hi-Waist Curve Skirt by Enza Costa**: The high-waisted detail on this skirt is fabulous.
- **Croc Embossed Leather Pencil Midi Skirt by Nordstrom**: White leather is definitely in this winter.
- **Veda Julia Leather Skirt**: This piece can elevate any outfit.
- **Faux Leather Midi Skirt by ZARA**: This skirt is simply perfect.
**Knee-Length Skirts**
- **Linen-Blend Bias-Cut Skirt by Gap**: I’ve been really enjoying white skirts recently. This one is simple yet chic. The button details add an interesting touch to an otherwise plain design.
- **Stripe Wrap Knit Skirt by Simonett**: The wrap detail on this knit skirt is very stylish. I love the easy, simple silhouette.
**Low-Rise Skirts**
- **Helen Low Waist Midi Skirt by Reformation**: This skirt exudes a perfect touch of glamour.
- **Pleated Hem Pencil Skirt by KASPER**: The hemline on this piece is incredibly lovely.
- **Low-Rise Suede Maxi Skirt by St. Agni**: Suede combined with a low-rise cut is absolutely stunning.
- **Low Waist Straight Skirt by TOTEME**: This skirt is a dream come true.
- **Pilcro Side-Slit Denim A-Line Midi Skirt by Anthropologie**: Low-rise denim in skirt form is undeniably cool.
**Pleated Maxi Skirts**
- **Pleated Midi Skirt by Madewell**: It’s easy to dress this skirt up or down.
- **Pleated Wool-Blend Twill Midi Skirt by RÓHE**: This wool skirt radiates luxury. I adore the academia-inspired style.
- **Belted Godet Pleat A-Line Skirt by MANGO**: This design is simple yet stylish.
- **Pleated Cape Skirt ZW Collection by ZARA**: I’m drawn to the subtle pleat details.
**Midi Skirts**
- **TWIST-DETAIL MIDI SKIRT by COS**: The twist detail is just perfect. I’m definitely taking this simple brown midi skirt with me.
- **Vince Waist Draped Midi Skirt**: I appreciate the draping on this piece.
- **Check Pleat Front Midi Skirt by MANGO**: This skirt is both chic and professional-looking.
- **Drawstring Midi Skirt by Madewell**.
Other articles
Chic Layering Guidelines: How Fashion Enthusiasts Combine Sweaters with Jeans, Skirts, and Everything Else
From denim to midi skirts, these stylish layering guidelines demonstrate how individuals are pairing sweaters in 2026 for chic, easygoing ensembles.
It's only February, but Zara has already released all the stylish spring trends—6 items that will sell out first.
Believe me, they won't last much longer.
Larger, Improved, and Here to Stay: 7 Iconic Noughties Bags That Are Still Making Waves in 2026
The designer bags are so appealing that we continue to be fascinated by them even after 30 years.
7 Beauty Trends for Spring/Summer 2026 Poised to Take Center Stage Next Season
Believe me, they'll be integrating themselves into your spring routine.
Explore Shop 29 for This Week's Top New Arrivals.
Before all of your friends do.
Every Stylish Girl Is Already Rocking This Chic Outfit Pairing for Spring.
Sheer tights are currently the finest way to style miniskirts and tailored shorts this spring 2026, lending a refined touch to the outfit combination.
5 Winter Skirt Trends Everyone Is Pairing With Boots This Year
If you want to enhance your winter wardrobe, consider these five skirt trends that style icons are sporting all around. Explore the trends here.