Outfit Ideas
Dec 22, 2023

6 Cool Winter Outfits That Will Earn You So Many Compliments

by Harriet Davey

We're at that funny time of year again, aren't we? Though we're well into December, the days are varying between full winter chill and milder clear sky days. As a summer girl at heart, I've been searching to find ways to carry my favourite summer items into the colder season. It's the best way to ease yourself in, IMO.

Let us not forget that, although overcast, every other day is bright and mild. So I'm all about finding outfits that don't look and feel too heavy, but also provide enough coverage should the weather take a turn for the worse. I want these outfits to carry me through to late winter, too. So we need effortlessly cool looks that just work. This is why I've edited my recent saved Instagram posts to show you a selection of looks I'll be re-creating from now—from jumper dresses with chunky boots to knitwear with stand-out skirts, these six cool outfits will never fail you. Scroll on to see them.

6 cool transitional outfits: Francesca Saffari wearing slip skirt and jumper

Photo:

@francescasaffari

Style Notes: Knits have already made their way back into wardrobes, and Francesca Saffari (pictured) keeps hers luxe by mixing the textured style with a silky slip. The Adidas x Wales Bonner retro trainers (a great find on eBay) give the look that cool-girl twist.

Shop the look:

Arket Bouclé Jumper

This is Francesca's actual jumper, and it's part of a co-ord, too. Shop the matching Knitted Bouclé Skirt (£57).

Reformation Layla Silk Skirt

Layla Silk Skirt

A skirt so good, it comes in six other prints and colours.

& Other Stories Ribbed Knit Tank Top

& Other Stories

Ribbed Knit Tank Top

One of the best white tank tops.

6 cool transitional outfits: @kimturkington_ wearing a relaxed cardigan, wide-leg trousers and trainers

Photo:

@kimturkington_

Style Notes: If you're on the fence about pinstripe trousers feeling "cool" rather than corporate, I predict you'll change your mind now you've seen Kim Turkington wearing them. Going full cosy and down-to-earth with a chunky cardigan and trainers, this is total perfection.

Shop the look:

Free People Found My Friend Cardi

Found My Friend Cardi

Fact: You'll wear this all year round.

Toteme Crew-Neck Organic-Cotton T-Shirt

Crew-Neck Organic-Cotton T-Shirt

Because we all know Toteme does the best basics.

M&S Collection Pinstripe Wide Leg Trousers With Wool

Pinstripe Wide Leg Trousers With Wool

I predict these will be a new influencer favourite.

Converse All Star Low Trainers White Mono

All Star Low Trainers White Mono

These come in so many different colours.

6 cool transitional outfits: @nnennachem wearing a statement jacket and denim skirt

Photo:

@nnennachem

Style Notes: As a huge advocate of the denim skirt, this is a look I would wear any day of the week. For warmer days switch the jacket for a chunky (but equally eye-catching) jumper.

Shop the look:

Kitri Bonnie Green Vinyl Jacket

Bonnie Green Vinyl Jacket

This one has the wow factor—the faux shearling is detachable, so it's basically two jackets in one.

Split-Back Organic-Cotton Denim Skirt

Split-Back Organic-Cotton Denim Skirt

You'll wear a blue denim maxi skirt on repeat all year.

Per Una Suede Cow Boy Knee High Boots

Suede Cow Boy Knee High Boots

These new M&S boots are bound to be a favourite.

6 cool transitional outfits: Aniya Morinia wearing striped shirt and trousers

Photo:

@claire_most

Style Notes: In my opinion, every outfit should be as cosy and comfortable as this one looks. Better still, its a sleek combination. Sandwich cargo trousers and your trusty white tee between a shearling jacket and footwear, ensuring the warmest winter look. Plus, who knew tan and khaki were such a great pair.

Shop the look:

Mango Worn-Effect Shearling Jacket

Worn-Effect Shearling Jacket

Grab it in a size up for an oversized fit.

Arket Taffeta Cargo Trousers

Taffeta Cargo Trousers

At this point, cargo trousers are a modern classic.

Le Specs Outta Trash Sunglasses

Outta Trash Sunglasses

Sunglasses are a staple all year round.

6 cool transitional outfits: Marianne wearing bandeau top and jeans

Photo:

@shloka

Styles Notes: Often, the coolest outfits of all are the most simple. To prove my theory, just take a look at Shloka's seemingly simple pairing of a bold knit with jeans and heels. If it ain't broke…

Shop the look:

Whistles Cable Knit Jumper

Cable Knit Jumper

Such a great shade.

Zara Metallic Kitten Heel Slingback Shoes

Metallic Kitten Heel Slingback Shoes

Silver slingbacks will take any look to a whole new level.

6 cool transitional outfits: @isabellecoheen wearing knit dress and chunky boots

Photo:

@isabellecoheen

I'm the owner of six knitted dresses (last time I counted) and I can't rave about them enough. They're so easy to throw on no matter the weather, and now I want a greige style to add to my collection after seeing how Isabelle has styled hers.

Shop the look:

H&M Cable-Knit Dress

Cable-Knit Dress

When I'm not wearing this with chunky boots, I'd style it with knee-highs.

Mango Knot Handle Shopper Bag

Knot Handle Shopper Bag

This one is roomy enough for everything you own.

Isabel Marant Brindi Knot-Tip Leather Belt

Brindi Knot-Tip Leather Belt

A great belt to cinch in all your dresses.

& Other Stories Chunky Chelsea Leather Boots

& Other Stories

Chunky Chelsea Leather Boots

The cleated sole is such a cool update to classic Chelsea boots.