I’ve Fallen in Love With These Classic Winter Pieces, and I Think You Will Too

As a fashion editor, I have spent a lot of my career reporting on new trends, new labels and new ways to wear things. However, in an effort to slow down the trend cycle and buy items with longevity in mind, we are also conscious here at Who What Wear to dedicate as many stories to repeated outfit ideas, classic items and second-hand items. Personally, I always gravitate to simple pieces that have a timeless appeal.

Below, I’ve put together an edit of classic winter pieces that I really love, including fine knitwear to wear in place of a T-shirt, beautiful leather handbags, blazers in neutral shades and chunky ankle boots. In terms of brands, there are a number of labels I always turn to for a timeless aesthetic. At a higher price point, Nanushka and Totême are leading the way here, and on the high street, I’m consistently most impressed by Scandi brands Arket and & Other Stories for both quality and design. Keep scrolling to see 25 classic winter pieces I love.

So simple and so beautiful. 

I have a weakness for blazers, and this suit is so beautiful. 

The matching flared trousers are amazing too. 

Such a cool shape. 

The perfect black dress.

Everyone needs a classic cream jumper.

The dream coat. 

Gucci’s horsebit detailing will always be iconic. 

Arket is one of our favourite places for tailored jackets. 

A cashmere skirt? Hello.

Yes, this is actually from H&M. 

A scrunchie in plated gold. 


Chunky boots are a modern classic. 

As close to wearing a duvet as you can get.

What a jumper.

This falls beautifully. 

These are expensive but a great investment. 

This looks amazing in real life. 

You don’t get more classic than a Loewe bag. 

This will go with everything you own. 

These look so expensive in real life. 

I’d wear this with the leather trousers.

Simple but excellent. 

Such a fabulous colour. 

Next up, see our guide to the key trends for autumn/winter 2021.