Leggings May Be an Affordable Staple, But Wearing Them With These 5 Winter Trends Makes Them Anything But Basic

For those crisp mornings when you wake up already feeling behind and can’t bear to part ways with your cosy Olivia Von Halle pyjamas or If Only If night dresses, leggings arrive as a quick-fix solution to not only help you remain comfortable throughout the day, but also look incredibly chic. An antidote to the winter chill that sets in this time of year, leggings are a substitute for the sumptuously decadent loungewear styles we dream of wearing all day long.

While they’re no match for bundling up in your flannel duvet and snuggling into a pair of bed socks à la Bridget Jones, leggings prove a more socially acceptable way of serving the perfunctory requirement of staying warm and looking good. (Two of the most crucial things on Maslow's Hierarchy of Needs.)

And while I love a leggings outfit as much as the next person, I do have one slight problem with them. Because of their very elementary nature, I tend to feel like the chicest leggings looks can often feel a shade repetitive. Even as someone who has made a career of identifying and reporting on the latest sartorial happenings, I, too, fall into the trap of finding an ensemble formula that works, which has lately been teaming cropped leggings with a boxy high-neck knit and ruched loafers, and wearing it until the silhouette feels exhausted. A proud outfit repeater at heart, a quality that speaks to my sustainably minded approach to fashion, there’s, of course, nothing inherently wrong with this. But this season, I want to lean into dressing up more and challenge myself to be a bit more intentional about what I wear—yes, even a basic as affordable and accessible as leggings.

So, with that being said, I’ve taken it upon myself to compile a guide to the freshest trends you can inject into your next leggings outfit that will make it feel entirely new. Most of these trends will most likely already be something you possess too, given the timeless nature of the season, so these chic additions are merely an act of shopping your own wardrobe. From floor-length coats to funnel-neck jackets, scroll on for the key winter trends to wear with leggings.

The 5 Chicest Winter Trends to Wear With Leggings

1. Funnel-Necks

Style Notes: Despite holding a deeply unsexy name that reminds me of one of the most useless kitchen utensils ever created—truly, you have to be Molly Baz or Sophia Roe to own one of these–funnel-neck jackets are arguably one of the most in-demand items right now. Deeply relaxed and ideal for bundling up on brisk walks, throw this into your outerwear rotation and you’ll be left with a look that’s both in the know and ahead of the curve.

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2. Floor Length Coats

Style Notes: Though the jury is still out on whether or not leggings are suitable to wear to the office—some may feel they’re not formal enough for workplaces, while others believe that there is nothing inherently wrong or offensive about them that warrants them staying out of boardroom meetings—you can take cues from corporate staples to dress up any leggings outfit. Take the floor-grazing coat, for instance. Beloved by both preppy finance bros and mob bosses, this tailored staple is great at making anything it’s worn over appear a thousand times more expensive than its price tag may suggest. Better still, if you have a strict dress code, this style is long enough to cover up any sartorial misdemeanours that are coming your way.

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3. Flannel Shirts

Style Notes: Straight from the ‘90s, the humble flannel shirt is back. Once relegated to the wardrobes of grunge musicians, like Nirvana frontman Kurt Cobain, the former symbol of anti-establishmentarianism has ironically become one of the most sought-after styles by the mainstream. Thanks to labels like The Row and COS given the style a high fashion makeover, you’ll notice that every fashion insider can be spotted with one worn tied around their waist or slung over their shoulders. This look may prompt an eye-roll from anyone who lived through the style’s reign nearly three decades ago, but there is just something so effortlessly elegant about the look. I personally love wearing mine during my weekly weekend post-pilates pastry run to really cement the off-duty feeling I’m trying to achieve on my down days.

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4. Statement Accessories

Style Notes: Once you have your perfect trench coat and crisp white T-shirt figured out, why stop there? The mode that encompasses the entirety of 2025, at least in my humble opinion, is one of thoughtful and deliberate inclusions, whether that be through a bag charm that you bought on a holiday abroad or a brooch you picked up at a neighbourhood car boot sale. I’ve personally had a fixation with belt bags, like this one pictured here, and for days where I want to feel both sporty and sophisticated, I can’t think of a better way of doing so than through this statement accessory.

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5. Scarf Jackets

Style Notes: Combining two of the trends on this list, a fabulous coat and a statement accessory, is the scarf jacket. Cropped at the waist and boasting a built-in sheath of fabric that wraps so gracefully around the neck, this is the sort of thing that will have strangers stopping you in the streets to deliver a lashings of compliments. Simply pair with a polished boot or tasteful ballet flat.

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