Skip to content
Vanity Fair Fashion
Fashion

5 Simple, Anti-Trend Outfits Everyone Will Wear This Winter

By Swedan Margen

5 Simple, Anti-Trend Outfits Everyone Will Wear This Winter

Getting dressed can become tedious and repetitive during winter, particularly when you frequently wear the same outerwear and footwear over an extended period. This concept emphasises the importance of investing in high-quality, timeless, and unique garments you can wear repeatedly and never tire of. Plus, having the classic staples makes it easier to make outfit choices, especially on days when creativity feels limited.

With that in mind, we scoured Instagram for inspiration, seeking classic winter outfits that exude elegance and sophistication. These looks are not only effortlessly stylish but also remarkably easy to replicate. They consist of dependable styling formulas that stand the test of time—anchored in timeless pieces rather than fleeting trends. When shopping for wardrobe essentials, the items that will serve as the foundation of your everyday ensembles, it's crucial to prioritise quality and fit. By doing so, you can avoid the need for replacements, sparing yourself from purchasing another wool coat or leather jacket just a year later.

Continue reading to discover the five uncomplicated, anti-trend winter outfits that'll remain in style and ensure you'll always look polished and put-together.

5 Simple, Anti-Trend Outfits Everyone Will Wear This Winter

1. Wool Coat + Tailored Trousers + Loafers

Neelam wears a cinched coat, trousers, black flats, and a black bowler bag.

Style Notes: Cinch-waist jackets may be a major look in 2025, but that doesn't mean you have to buy a new topper to get the look. As seen here, you can use a tonal belt to nip the jacket in and create that flattering fit. Since the jacket is the outfit, style influencer Neelam kept the rest of her outfit simple, opting for tailored pants, sleek clogs, and a leather bowling bag.

Shop the Look:

Poldo Virgin Wool Wrap Coat

'S Max Mara

Poldo Virgin Wool Wrap Coat

The darker grey hue is calling to me.

Mija Croc-Effect Leather Belt

DÉHANCHE

Mija Croc-Effect Leather Belt

You can lso use an actual belt to get that dramatic cinched-in effect.

Mason Pant Es

Reformation

Mason Pant Es

These are a bestseller for good reason.

Loafers

These look way more expensive than their price tag.

Medium Leather Tote Bag

Miu Miu

Medium Leather Tote Bag

2. Leather Jacket + Sweater + Jeans

Viki wears a brown leather bomber jacket, gray turtleneck, gray pants, white flats, and an ivory east-west bag.

Style Notes: A great way to elevate gray jeans and a matching sweater into a stylish outfit is by pairing them with an elegant brown leather bomber jacket. Just like black and white, the combination of brown and grey always works—it looks sophisticated and polished every time. To take the look up a notch, consider adding an east-west bag and ballet flats.

Shop the Look:

Clint Oversized Paneled Distressed Leather Bomber Jacket

NOUR HAMMOUR

Clint Oversized Paneled Distressed Leather Bomber Jacket

Nour Hammour's jackets are so good right now.

Marion Merino High Neck Jumper-Charcoal Melange

Boden

Marion Merino High Neck Jumper-Charcoal Melange

'90s Pinch Waist High-Rise Straight-Leg Organic Jeans

AGOLDE

'90s Pinch Waist High-Rise Straight-Leg Organic Jeans

Fashion coolest dressers are opting for grey denim.

Luna Slipper / Ecru Leather

Le Monde Béryl

Luna Slippers

The white flats will contrast nicely against the grey and brown.

3. Faux Fur Coat + Midi Dress + Tights + Pumps

Sylvie wears a brown fur coat, black midi dress, sheer tights, black flats, and black leather gloves.

Style Notes: Opt for a luxurious faux fur coat and a sleek little black dress when venturing into the chilly weather to enjoy drinks with friends. To elevate your ensemble and add a touch of sophistication, slip on classic pumps and sheer tights, mainly if you're showcasing your legs.

Shop the Look:

Toteme, Soft Shearling Coat

Toteme

Soft Shearling Coat

Skims Soft Lounge Maxi Dress

Skims

Soft Lounge Maxi Dress

Skims dresses are universally flattering.

Calzedonia 30 Denier Tights in Black

Calzedonia

30 Denier Tights

Tights season is finally upon us.

Pointed-Toe Leather Heeled Shoes - Women | Mango United Kingdom

MANGO

Pointed-Toe Leather Heeled Shoes

A unique style that you don't often see on the high-street.

4. Long Coat + Jeans + Boots

Annabel wears a gray long coat, black scarf, gray sweater, blue jeans, and black boots.

Style Notes: There's a saying: "If it isn't broken, don't fix it." That's exactly how I feel about pairing vintage jeans with a crewneck jumper and a white tee that peeks out underneath. It's a simple combination, yet it often looks as if a stylist put it together. To give this look a modern twist, consider adding a scarf coat and square-toe boots or loafers.

More Fashion

5 Simple, Anti-Trend Outfits Everyone Will Wear This Winter - Vanity Fair Fashion