Stylist Picks for Autumn/Fall Skirts 2025: The Season's Most Coveted Silhouettes

Forget everything you thought you knew about autumn dressing—skirts are officially the hero pieces of autumn/winter 2025, with designers from Saint Laurent to Simone Rocha proving that these feminine silhouettes are the secret weapon for chic cold-weather dressing. After spending countless hours analysing the runway shows and street style moments, I can confidently say that this season's skirt selection offers something for every style personality, from the minimalist who loves a sleek pencil skirt to the maximalist drawn to leopard print and sequined embellishments.

The Pencil Skirt Renaissance

The pencil skirt has undergone a dramatic transformation this season, evolving from its traditional office-wear associations into something far more versatile and exciting. What I'm particularly loving is the emergence of the maxi pencil skirt—think floor-grazing lengths that offer all the polish of a classic pencil with added drama. Calvin Klein led the charge with collarless skirt suits in greys and pinstripes, while Saint Laurent presented bright coloured versions that prove this silhouette works just as brilliantly for evening as it does for the boardroom.

For high street options, Zara consistently delivers sharp, affordable pencil skirts in both classic and contemporary cuts. Their autumn collection features everything from leather-look styles to pinstripe versions that rival designer pieces. Massimo Dutti offers exceptional tailoring at mid-range prices—their pencil skirts have that expensive-looking finish that makes them perfect for both professional and weekend styling. For something more accessible, M&S has embraced the trend with jersey fabrics that resist creasing and offer comfort without sacrificing style.

Pleated Perfection

This season's pleated skirts have shed their preppy, collegiate associations in favour of something more sophisticated and adult. Simone Rocha's shredded pleated skirts at London Fashion Week proved that this silhouette can be both romantic and edgy. I'm particularly drawn to midi-length pleated styles in rich autumn tones—they're universally flattering and endlessly versatile.

COS excels at elevated minimalism, and their pleated skirts this season are no exception. Look for their wool-blend versions in camel and chocolate brown—two of autumn's biggest colour trends. Whistles offers beautifully crafted pleated midi skirts that sit perfectly at that sweet spot between high street and premium pricing. For budget-conscious shoppers, H&M has embraced the trend with flowing pleated styles that look far more expensive than their price point suggests.

The Wild Side: Leopard Print Dominance

If there's one print that dominated the autumn/winter 2025 shows, it was leopard. From Fendi's full leopard suits to Khaite's sultry interpretations, this classic print has evolved beyond outerwear into every category imaginable. The key to wearing leopard print skirts this season is treating them as a neutral—they pair beautifully with black, white, camel, and surprisingly, even other prints when styled thoughtfully.

Mango has produced some exceptional leopard print pieces this season, including a silk-effect bias-cut midi that looks remarkably similar to designer versions. River Island offers more accessible options with their animal print collection featuring everything from mini skirts to flowing maxis. For those seeking something truly special, independent brand Paris Georgia from New Zealand creates bias-cut leopard skirts that have achieved cult status among fashion insiders.

Slip Into Something Luxurious

The slip skirt trend shows no signs of slowing down, with this season's versions featuring delicate lace trims, embroidery, and sequined embellishments. These pieces work brilliantly for transitional dressing—pair with a chunky knit and boots for day, or switch to a silk camisole and heels for evening.

Reiss offers beautifully cut slip skirts in silk and satin finishes that feel appropriately luxurious for the price point. Their bias-cut styles are particularly flattering and move beautifully with the body. For premium options, Me&Em creates sophisticated slip skirts in rich jewel tones that work seamlessly from desk to dinner.

Check Mate: Tartan and Heritage Prints

Inspired by Dior's Mary Queen of Scots cruise collection, tartan and check prints are having a major moment. These heritage prints feel particularly appropriate for autumn, offering a sophisticated alternative to florals or geometric patterns.

Jigsaw excels at this trend with their wool mini kilt skirts that feel fresh rather than costume-y. Barbour naturally embraces heritage checks with their tweed skirts that pair perfectly with their iconic wax jackets. For something more unexpected, look to Ganni, the Danish brand known for their playful take on Scandi minimalism—their check skirts often feature unexpected proportions or contemporary cuts that feel thoroughly modern.

Premium and Luxury Recommendations

For those looking to invest in premium pieces, Toteme offers impeccably cut midi skirts in luxurious fabrics that epitomise Scandinavian minimalism. Their neutral palette and refined silhouettes make every piece feel like a wardrobe essential. At the luxury end, Loewe creates architectural skirts that blur the line between clothing and art, while The Row offers whisper-soft cashmere and wool styles that represent the pinnacle of quiet luxury.

How to Style This Season's Skirts

The beauty of this season's skirt trends lies in their versatility. Pencil skirts look equally chic with oversized blazers and fitted turtlenecks. Pleated styles work brilliantly with cropped jumpers and ankle boots. For leopard print pieces, I recommend keeping everything else relatively simple—a black roll-neck and knee-high boots create the perfect backdrop for the pattern to shine.

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The Tellar Fashion Hub

Beyond sizing, Tellar offers a comprehensive Fashion Hub—a library packed with free posts from top stylists. Honest, unbiased, independent, and always free, this is where you'll find expert style advice, curated top picks, and honest brand recommendations.

For more comprehensive styling guidance, explore these essential Tellar resources:

The Bottom Line

This autumn's skirt trends prove that feminine dressing and practical cold-weather styling aren't mutually exclusive. Whether you're drawn to the sharp sophistication of a pencil skirt, the romantic appeal of pleated styles, or the wild confidence of leopard print, there's never been a better time to embrace skirts as a wardrobe staple. The key is choosing quality pieces that you'll love wearing for years to come—and with Tellar ensuring perfect sizing every time, you can shop with complete confidence knowing that your investment pieces will fit flawlessly.