15 pairs of winter shoes that never go out of style

Winter is a time of year when all we want to do is rug up and stay put. Needless to say, our motivation to do much of anything on a cold, blustery and short-lived winter’s day is practically non-existent – and this is especially true if we don’t have the right garments on hand to keep us toasty and comfortable as we traipse through our to-do lists. Winter footwear poses a particular problem for sandal-wearing Aussie beachgoers who’d much rather throw on a pair of Havaianas year-round if they could. But cold feet are never fun – literally or metaphorically – and less-than-practical for the kinds of temperatures southern Australians are put through from June to August.

If you’re looking to invest in a pair of winter-worthy footwear, but want them to last more than a single season, we’ve rounded up 15 pairs of winter shoes that never go out of style (or at least, not according to the RUSSH team).

1. Dries Van Noten Suede-Trimmed Leather Sneakers

Love them or hate them, a great pair of sneakers will always have a place in a well-rounded wardrobe, especially in the winter months. Bringing a retro athletic appeal to our Sunday walks are the Dries Van Noten leather-trimmed sneakers. While perhaps better suited to sidewalks than trails (particularly in this chic white hue), the design’s sleek yet casual feel makes for a versatile and ultra-comfortable option. Pair with your workout gear for a vintage athleisure feel, or throw on with your favourite pair of jeans.

2. Maison Margiela Black Tabi Ballerina Heels

The humble ballet flat will always have a place in our capsule winter wardrobe, and this pair by Maison Margiela are a perfect example. With a slight heel and the brand’s signature split toe detail, they’re a slightly amped-up take on the classic. Not only are they timelessly fashionable, versatile and able to be dressed up or down, they are also (if you get the right pair, of course) incredibly comfortable and pragmatic; the perfect footwear for a day spent traipsing around town, or dancing the night away at a local bar.

3. Birkenstock Shearling-Lined Clogs

Hear us out! The Birkenstock signature Boston clog, rendered in suede and with a cosy shearling-lined footbed, is a winter saviour. Don a pair of your fuzziest sock and slip these bad boys on and off for those last-minute errands or outdoor activities that you really can’t be bothered to lace, buckle or zip yourself into another pair of shoes for. This iteration in a chestnut brown is our current favourite.

4. UGG Classic Ultra Mini Shearling Boots

What kind of winter shoe wrap up would this be without mention of the iconic Ugg boot? Like walking on a cloud, these fluffy, sheepskin lined booties are feature a chestnut suede upper and thick, rubber soles for those times when you simply need your slippers to leave the house with you, and to be all-terrain. If you’re not into half-calf Y2K favourites, why not try these Bella Hadid-approved low-top minis?

 

5. Miu Miu Unlined Leather Boat Shoes

No longer just for dads on actual yachts, the boat shoe has made a serious comeback in 2025, and is up there as our favourite every day winter shoe. This brown pair by Miu Miu are an obvious hallmark of the style, but there are endless options to choose from online. They’re sturdy and versatile, and ooze a certain kind of ‘preppy’ sophistication that a pair of leather loafers can sometimes lack.

6. AEYDE Uma Mary Jane Ballet Flats

Relive your school days with a pair of leather buckle-up Mary-Jane shoes, only this time with a grown up twist. This Aeyde pair (available in several colours) are a chic option to dress up with your favourite frilly socks, and best believe there’s good reason why they became a schoolyard favourite for restless kids and teens – the style is comfortable and durable.

7. STAUD Western Wally Boots

Some may argue that knee high boots are a bit of a passing fad at the moment, but we’d beg to differ. Whether you prefer Western, riding, or moto-leaning styles, sturdy boots have a long and illustrious history; no small feat for a fashion trend. This pair, by Staud, have are slightly Cowboy-esque, without feeling too trendy, making them a great investment piece for your wardrobe this winter and beyond.

8. Onitsuka Tigers Mexico 66 SD

The enduring popularity of the tennis shoe has made it a timeless investment – if you can get your hands on a pair. Styles like the Onitsuka Tigers are constantly sold out nearly everywhere you look, they are a versatile and bold shoe that work trans-seasonally with just about every outfit.

9. Camilla and Marc Rhys Smooth Patent Pump

A pair of black pumps are the footwear equivalent of the LBD. Here, the cult classic style receives a contemporary upgrade, with the addition of a decorative detachable gold chain that hangs gently around the ankle. Equal parts sturdy and elegant, these shoes are just as useful for a day in the office as they are after work drinks.

10. Saint Laurent Le Loafer logo-embellished suede loafers

The loafer is a veritable staple; evolved from a menswear background to become an accessory donned by the most fashionable women. Each season, its silhouette might be slightly updated – suede fabrications and chocolate brown hues are all the rage in 2025 – but realistically, a staple pair in any shade of leather will last you for years if well-looked after.

11. Charles & Keith Kirke Buckled Mid-Calf Biker Boots

Tough, timeless, and built for winter, chunkier biker boots balance form and function effortlessly. Take this pair, by Charles and Keith: their sturdy sole and structured silhouette offer cold-weather durability, while the buckled details add a sharp, rebellious edge.

12. New Balance 2010 Grey Days

There’s something enduring about a chunky, tonal sneaker in winter. Styles like the New Balance 2010 Grey Days are grounded in utility, but elevated through subtle design choices: layered textures, thoughtful palette, and a shape that nods to heritage while staying firmly modern. They move easily between function and form, making them a staple year after year — weatherproof or not.

13. Jo Mercer Goldie Casual Flats

Studded ballet flats strike the perfect balance for winter: polished but with just enough edge to cut through heavier textures. When boots feel too much and sneakers too casual, we love this pair by Jo Mercer. The hardware gives them weight, grounding more delicate silhouettes like silk skirts or tailored wool. A winter essential for days that call for elegance without compromise.

14. Tony Bianco Fantasy Chocolate Nappa Boots

Heeled boots are winter’s answer to elevated dressing—literally and figuratively. They elongate the silhouette, add structure to soft layers, and bring a sense of intention to even the most thrown-together look. When the temperatures drop, it’s about pieces that feel strong yet sensual, and a heeled boot does both with ease. The Tony Bianco Fantasy boots in Chocolate Nappa embody this perfectly: rich in tone, sculptural in shape, and just the right height to carry you from day to night with quiet confidence.

15. Prada Leather Chelsea Boots

When heeled boots feel too polished and knee-highs too much of a statement, the Chelsea boot steps in. These ones, by Prada, offer a stripped-back elegance, with just enough edge to anchor winter layers without overpowering them. Sleek but grounded, they’re the kind of alternative that works with everything—trousers, oversized coats, bare legs and stockings.