As the New Year approaches, it’s the perfect time to refresh your winter wardrobe with cozy classics and on-trend styles. This season’s runways have been all about earthy palettes and nostalgic nods, think heritage tartans, rich knits, and luxe textures glamour.com. Gone are the days of drab winter dressing: smart layering, statement coats, and cozy fabrics can make even the coldest days feel stylish.
In this guide, we spotlight the winter sale pieces you need now, from woollen plaid skirts and structured blazers to velvet party dresses and chic bags. Each item is chosen for warmth, style, longevity, and that vintage-inspired flair our UK audience loves. Let’s dive into the essentials that will keep you warm and on-trend well into 2025.
Winter styling is about textures and layers. Swap fragile summer fabrics for heavyweight materials like wool, tweed, corduroy, and velvet. These denser textiles not only insulate against the cold but also add visual depth to your outfits. As Timeless London notes, woollen skirts are “perfect for winter”; their thick weave traps warmth while draping elegantly. In practice, this means choosing pieces like a wool circle skirt that swirls above knee-high boots, or a corduroy midi that channels vintage charm. By focusing on material quality (think high-wool-content blends), you ensure each sale find isn’t just on-trend this season, but built to last for winters ahead.
Luxe Wool Skirts: Cozy Yet Chic
Wool skirts are the backbone of a warm winter wardrobe. Unlike lightweight cotton or denim, a woollen skirt brings insulation and old-world polish. Vogue Magazine sums it up: grey wool skirts (and by extension any wool skirt) have become the backbone of my cold-weather wardrobe, their blanket-like thickness relied upon when temperatures plummet”.
Timeless London’s collection features many such vintage-inspired wool skirts on sale now. For example, the Sophie Chocolate Woollen Midi Swing Skirt is made of luxury wool blend, combining warmth with a classic 1950s circle silhouette. At a modest midi length, it traps even more heat, while the rich chocolate hue adds depth to an outfit.
Skirts also invite playful colour and pattern. Plaid and tartan prints are having a major moment (more on that next), but even solid or subtly checked skirts are winter staples. Pair a grey or camel wool skirt with black opaque tights and knee-high boots for an effortlessly sleek look. The fabric’s texture itself adds style: a ribbed or tweed skirt reads cozy-chic, telling a seasonal story every time you step out.
How to wear wool skirts in winter: Start with warm base layers (thermal leggings or thick tights). Then let the skirt shine: choose a high-waist wool midi and tuck in a fitted knit. As Timeless London advises, “a high-waisted circle skirt like the Sophie Purple Check Swing Skirt practically begs for a tucked-in knit”. Turtlenecks or cable-knit sweaters in complementary hues accentuate the 1950s silhouette and keep your core warm. Finish with boots. Knee-high or heeled ankle boots create a continuous line with your skirt, elongating your legs and anchoring the outfit.
Sale Skirt Picks: Our winter sale highlights some of the most sought-after wool skirts:
Sophie Grey and Pink Swing Skirt – A heritage-inspired tartan in soft grey and blush. (Versatile enough to mix with neutrals or pops of colour.)
Sophie Houndstooth Woollen Check Tartan Midi Swing Skirt – A black & white wool houndstooth tartan that pairs effortlessly with bold hues like red or classic black blazers.
Sophie Camel Woollen Check Tartan Midi Swing Skirt – Warm camel tones in a timeless plaid; a rich neutral that elevates any knit or jacket.
Wendy Red And Black Plaid Mini Skirt – A playful tartan mini perfect for layering; wear with tights and boots for weekend ease.
Mika Mini Chocolate Woollen Skirt – A mini wool skirt in deep brown for those who prefer vintage minis (just add a thick knit and tights!).
These skirts are on sale now, don’t miss the chance to snag cozy classics at a discount. Every skirt is engineered for winter: heavy wool blends, full-circle cuts, and plaid prints that recall holiday warmth. Remember, a swishy woollen skirt not only keeps you snug but also makes a joyful statement, as one style guide puts it, a tartan skirt adds “personality” to your outfit and can even be a mood-booster in grey winter.
Plaid Patterns: Heritage Meets Haute
This winter, plaid and tartan prints are everywhere. Originating in Scottish history as clan tartans, checked fabrics have been reinvented by everyone from Burberry to McQueen. On the fall/winter 2024–25 runways, designers sent models down in heritage plaids paired with knee-high boots and tailored coats. The result: an English countryside vibe on the catwalk, yet completely wearable in city life. As Glamour’s trend report notes, “earthy plaid, full skirts, luxuriously thick outerwear, hallmarks of rural English aesthetic” dominated the season. In short, plaid skirts are an “enduring trend” for winter.
Why do plaid skirts rule winter? For one, they feel cozy. The traditional checkered motif evokes images of cabin blankets and nostalgic school uniforms. And like all wool skirts, plaid versions inherently provide warmth and comfort. In practical terms, layer a wool plaid midi with tights and boots, or a mini with thick tights, and you have an effortlessly put-together cold-weather outfit. Their versatility is unmatched: pair a plaid skirt with a leather jacket and combat boots for edgy flair, or swap to a chunky knit sweater for a classic cozy look.
Fashion editors say a well-fitting plaid skirt suits everyone. Pleated minis and A-line midis flatter many shapes, and the pattern itself can even create slimming visuals depending on the cut. Best of all, plaids transcend trends; this season’s grunge-inspired tartans coexist with pastel-colored checks, meaning you can find one to express your personal style (from bold red & black plaid to subtle grey & pink tartans).
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Why You Need One Now: Plaid skirts blend vintage and modern. They’re on-trend for Winter 2024/25, yet also a perennial classic. Buying one now means years of wear to come. Even Vogue notes that after seeing tartan everywhere, the quietly powerful plain grey wool skirt has become the go-to staple, but the real story is that check patterns themselves are having a renaissance. British Vogue and Who What Wear have both highlighted the plaid skirt.
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Top Plaid Picks: Stock up on these sale skirts to ride the plaid wave:
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Sophie Navy & Green Midi Skirt - Timeless London – A bold navy-green wool tartan midi; a rich, versatile piece that plays well with cream knits or black jackets.
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Sophie Black and Red Check Swing Skirt – A vibrant black-and-red woollen swing skirt, perfect for holiday parties or weekend strolls (think layered with a black turtleneck).
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Sophie Sage Green Woollen Check Tartan Midi Swing Skirt – Soft sage-green plaid for a subtler take on tartan; looks gorgeous with nude or brown accessories.
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Sophie Forest Green Woollen Check Tartan Midi Swing Skirt – A dark pine tartan, classic and elegant, that adds forest-toned warmth to grey winter skies.
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Sophie Red & Dark Green Midi Skirt – A festive red-and-green tartan, evoking Christmas vibes; pair with solid knits for a balanced look.
Each of these plaid skirts features high-quality wool blends and classic silhouettes (pleated or full-circle swing) that fall just below the knee, creating that elegant drape. As one style guide notes, a skirt that “falls just below the knee” in a flattering A-line sweep accentuates the waist and gives you a glamorous twirl with every step. Embrace this nostalgic pattern now while the sale is on; it’s the quintessential way to infuse your wardrobe with heritage charm.
Step Out in Boots: The Perfect Winter Pairing
No skirt outfit is complete without the right boots. In winter, boots are both practical and fashionable: they keep feet and ankles warm while balancing the skirt’s length. In fact, boots + skirts is a formula fashion editors swear by. A key trick is continuity: wearing knee-high boots under a midi skirt creates a seamless line from hip to toe, which “makes your legs look like they go on forever”. For instance, tall black suede or leather boots with a dark plaid skirt will elongate your silhouette and ground the look.
Heeled and flat boots each have their place. Block-heeled knee boots in suede or leather elevate any midi for a polished, mid-century chic vibe. Ankle boots can work too, just pair them with thick tights in the same colour to avoid exposing skin to the cold. Imagine burgundy tights and boots under a charcoal swing skirt, or tan boots peeking out from a camel midi; the right contrast or match can make your legs appear longer and keep you cozy. Even patterned boots (like a rich burgundy or velvet lace-up) can add a playful twist at the hem.
Boot essentials: Look for leather or suede boots with quality lining (faux shearling or thick footbeds) so they feel like slippers inside. A well-chosen pair not only complements your sale skirts but also anchors the outfit on winter streets. Pro tip: polished leather or suede boots in black, brown, or grey will take you through winter in style, while a pair in wine red or moss green can inject a festive note into holiday outfits.
Jacket & Blazer Layering: Sharp Meets Snug
Top off your winter looks with a statement jacket or blazer. Timeless London’s wool jackets and blazers are designed to layer seamlessly over skirts and dresses, adding structure and warmth. Blazers have evolved beyond office wear into everyday staples. Today’s trends favour innovative cuts and rich textures on these classics, so you’ll find everything from cropped double-breasted jackets to cozy cardigans in our winter sale.
Consider double-breasted wool jackets in warm tones (brown, charcoal, camel) for a vintage vibe. A cropped brown double-breasted style, for example, nods to 1950s tailoring but with a shorter, modern cut. Classic Houndstooth and Check Jackets (like our Houndstooth Check Cropped Jacket or Green Woollen Cropped Jacket) bring retro appeal; these knit or tweed blazers look just as elegant with a matching skirt as with jeans. In fact, pairing a check blazer with a Sophie Black and Rust Woollen Braces Tartan Midi Swing Skirt is a fashion editor-approved mix of patterns and heritage textures.
Crocodile top-handle and crossbody bags are trending (see next section), so think of jackets as part of an ensemble. A cropped Suede Blazer can add tactile interest; suede is indeed having a “major moment” for 2025, while a wool-blend cardigan with subtle embellishment (like the Caspia Wool Cardigan with Embellishment) offers polish and comfort. Our sale collection even includes two-piece suit sets: coordinate a blazer with its matching skirt or trousers for instant “power dressing” that still feels cozy (pair a blazer-trouser set with a simple knit under for a softer touch).
Lastly, don’t overlook outerwear: a classic long wool coat or faux-fur coat layered atop everything will complete the look on the coldest days. For this guide, we focus on sale pieces, but know that a timeless coat (think camel or grey) will serve you beyond the sale. When the weather really drops, throw on a velvet blazer (velvet is also trending!) or the most insulating outerwear you own over your woollen layers.
Shop now from our woollen collection for our cozy jackets, cardigans, and more. And for tailored styles, get the trending jackets now. Our sale blazers come in vintage cuts and modern fits to elevate any outfit.
Velvet & Other Luxuries: Party-Ready Pieces
While wool, plaid, and boots ground your everyday looks, winter is also the season of rich fabrics and holiday glamour. Velvet reigns supreme in eveningwear. From draped velvet dresses to sumptuous velvet blouses, this fabric delivers both elegance and extra warmth. Vogue even notes that velvet “exudes festive luxury” in fall and winter, with modern cuts pushing it from formalwear into everyday chic.
Our sale offers several velvet and luxurious evening pieces. The Malika Burgundy V Neck Velvet Blouse is a great example: deep burgundy velvet feels opulent and pairs perfectly with black trousers or a wool skirt. For dresses, the Ziah Midi Velvet Dress and Rhia Black Midi Velvet Fitted Midi Dress are party-perfect; their plush sheen and fitted silhouettes stand out at holiday gatherings. Velvet also shines in colors: a Balia Green Velvet Midi Fit and Flare Swing Dress in emerald green is ideal for festive occasions.
Remember, velvet is “warm and elegant”, a timeless winter signaturevogue.com. For casual days, you could even trim a wool jacket with faux velvet or mix it into accessories (velvet scrunchies, headbands). But for the sale pieces, think holiday tables and New Year’s Eve photos: grab one of our luxe velvet tops or dresses on sale and you’ll sparkle without shivering. These are the pieces that make winter feel decadent.
For quick hits of velvet and shine without full dresses, consider how to layer sparkle into your wardrobe. A velvet top under a tweed blazer, or a silky blouse under a wool jumper, can add interest. And of course, holiday knitwear and novelty sweaters (like a fun Teddy Dress in plush fleece) also fall into this festive category; they inject a bit of playfulness or shimmer for the season.
Handbags & Accessories: The Finishing Touches
No outfit is complete without the right bag. This winter’s handbag trends blend practicality with polish. Suede and leather are front and centre. Vogue’s handbag trend report highlights rich suede totes and top-handles as fall favourites. Indeed, chocolate-brown or rust-colored suede feels luxurious and textural (“feels luxurious without sacrificing wear. Our Esme Suede Rust Handbag exemplifies this trend, a supple rust suede that pops against neutral coats, echoing those “chocolate brown suede” luxury look.
For classic appeal, black calf-leather or structured shapes never go out of style. A mini or boxy top-handle bag evokes a retro vibe. Vogue notes that ‘50s-style top-handle bags are back in a big way. Our Sienna Black Handcrafted Leather Handbag fits right in: it has that ladylike feel with a modern edge. Similarly, our Lulani Mini Black Handcrafted Bag is a cute black leather piece that nods to the new-pocketbook silhouette, perfect for day or evening.
Other chic options: the Cabas Black Calf Leather Bag is a roomy tote style for every day, and the Lulani Mini Chocolate Handcrafted Bag in deep brown leather is ideal for adding a warm neutral tone. A suede option like Esme Suede Rust Handbag or even a patterned textile bag can elevate even the simplest wool knits. The key is rich, fall-to-winter colours: navy, burgundy, caramel, forest green and black all dominate the season. These hues also coordinate beautifully with our skirts and coats, for example, a tan bag and boots set off a dark plaid ensemble.
Whenever you snag one of our sale handbags, think about how it completes an outfit. A structured bag automatically adds polish. For example, pair the Lulani Mini Black with a grey wool coat and scarf for a sleek winter commute look. Or let the Esme Suede Rust stand out by teaming it with camel or olive knits. Whichever style you choose, quality leather and suede mean the bag will be a trusty companion season after season.
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Bag Tip: Keep one top-handle or box bag for special occasions and a crossbody for daily wear. A little gilt hardware goes a long way. And remember to buy our trending handbags for women while they’re on sale. Classic designs in these warm-tone leathers are easy to love year-round. Buy our trending handbags for women now and carry your winter essentials in style.
Fresh Finds: Dresses, Separates, and Suiting
Besides skirts and velvet, our sale includes other gems. Dresses in winter fabrics can be layered or worn alone. For example, the Lula Rose Print Dress in Viscose adds floral charm and can be worn under a cardigan or blazer for work. The Cherise Dress (a knitted floral pattern) is perfect for daytime warmth. For a playful look, try the Rege Mini Dress. Pair it with thick tights and boots to balance the short hem. Even lighter dresses like the Sonny Midaxi Yellow Gingham Dress get new life in winter: add a jacket and boots, and the bright gingham lifts grey winter skies. Our Teddy Dress (in plush faux-shearling) brings instant coziness and holiday spirit.
If trousers are more your thing, the Alex High Waisted Trousers can be a fresh alternative. Wear these wide-leg wool pants with a fitted jumper and blazer for an elegant suits-inspired outfit. On that note, be sure to explore our latest two-piece suits, a matched set of blazer and skirt, or trousers makes getting dressed effortless. A double-breasted suit in tweed or wool is especially festive and versatile: imagine one of our Sophie blazers with a coordinating skirt from this list, or even mixing colours for a colour-blocked suit look. A two-piece suit is a powerful way to refresh your winter wardrobe with a single purchase, and it’s easy to pair each piece with other sale items (e.g. wear the blazer with denim or the skirt with a sweater).
Conclusion: Start the Year in Style
Refreshing your winter wardrobe doesn’t have to be daunting. With our curated winter sale pieces, you can update key looks affordably. From timeless tartan skirts and wool blazers to sumptuous velvet dresses and chic leather bags, each item is crafted for both style and longevity. Layer them together with a wool skirt with boots and a cardigan; a velvet top under a blazer with corduroy trousers, and you’ll master the “warm and stylish” formula this winter.
Timeless London pieces blend nostalgia with modern wearability. By investing in quality materials and vintage-inspired cuts (especially at sale prices), you’re choosing smart, sustainable style that will literally keep you warm year after year. Embrace this season’s trends, the earthy tones, rich textures, and classic silhouettes, and you’ll step confidently into the New Year, cozy, chic, and camera-ready for all that 2025 has to offer.
Questions about fit, styling or care? We’re here to help. Shop now and get the looks you love now, before your favourite winter wardrobe refresh pieces are gone.
