We’ve officially reached that time of year where getting dressed can feel a bit rough. I find myself struggling to pull together outfits from my winter wardrobe and feel rather uninspired. I find myself looking through Pinterest for style style looks I’ve pinned as well as my own personal archives of old outfits to get ready in the morning. 

We have several months of winter weather still ahead so I thought I’d share some winter outfit ideas from years past to give you some inspo when it comes to outfit arranging for cold weather. Shopping for some new key pieces to style? Don’t miss my shopping curation of pieces for cute winter outfits at the bottom of this post.

Consider this post your guide to discover easy, chic winter outfit ideas for 2026. From casual weekend looks to elevated cold-weather formulas, get styling tips for outfits you’ll actually wear.

Winter Outfit Ideas

My style becomes even more neutrals focused in winter. I rely heavily on my collection of favorite winter coats to pull outfits together and look to accessories to make an impact more while bundled up.

You can shop pieces inspired by each of these looks in the widget at the bottom of the post. Want even more winter outfit ideas in 2026? Don’t miss my Fall/Winter Outfits Pinterest Board.

Striped Sweater + Wide Leg Denim + Kitten Heeled Boots

This is an easy winter formula to look polished and put together. I’m wearing this sweater (recommend sizing up) with these wide leg jeans and these boots. The coat is by J.Crew.

If you prefer wearing more color, consider a neutral base + a statement coat. 

I think Nour Hammour is making the best statement coats in the market right now. Fore more of a range of price options, check out Revolve’s selections of coats.

Striped Sweater

A great way to add visual interest to a winter outfit under a coat is a striped sweater. This brand makes my favorites.

Navy and Black Outfit

If bare ankles are possible, I love loafers with leather pants and then a navy jacket. It’s such a stylish, timeless and very French inspired color palette for a winter outfit. 

Cold-Weather Dressy Looks

Faux Leather Maxi Skirt + Trench

Why do cold weather dressy looks feel so hard sometimes? 

For another dressed up winter look try a faux leather maxi skirt with knee high boots and topped with a borrowed-from-the-boys oversized trench (size down in this one!)

Cashmere Sweater + Satin Trousers

Dress them up with a heel, dress them down with a sneaker. I love the versatility and comfort of a satin trouser. Wearing above my favorite Colby pants by La Ligne. But I also own these beautiful Vince ones and love them. Size M in both.

Don’t miss shopping all My Favorite Cashmere Sweaters if you’re looking for some quality recommendations.

Related: What to Wear with Chanel Slingbacks

Dark Florals + A Blazer

While I often reach for florals only in spring and summer, I love the contrast of a floral in a darker shade and topped with a heavy weight wool blazer and paired with suede boots.

Reformation does the best florals I think. (Just be sure to size up!)

Sweater Dress and Over the Knee Boots

Sweater dresses are one of my most reliable looks for dressier occasions in winter. But I often see them styled improperly so if you’re looking for some inspiration, don’t miss my How To Style Sweater Dresses guide. 

Me + Em makes excellent, noteworthy knit dresses. 

Velvet Dress

For dressier nights in winter I love velvet dresses. Wearing this one in a size L above with these riding boots.

Weekend Winter Outfits

Leather Pants + Sneakers

I love dressing up and dressing down faux leather pants in the winter. For dressier looks I add a favorite dress bootie but for daytime outfits, I reach for a pair of streamlined sneakers. 

I love this look as a weekend winter outfit that reads casual & chic.

Quilted Jacket

A chic quilted jacket adds a polished yet sporty flair to any outfit! Size down in this one – I’m wearing a small above.

If you prefer a collar, try this style.

Riding Boots + Wrap Coat

A good pair of riding boots paired with a simple wrap coat is great for extra cold days.

Related: What to Wear to Paris in Winter

Winter Weekend Athleisure

This is my easy winter outfit formula 2026.

This outfit is what you’ll often find me in during casual winter weekends when I go for coffee or bagel runs in the neighborhood or go on walks with friends. I grab a pair of my favorite leggings, pop on my favorite comfy walking shoes and top with a beanie and a favorite coat.

Related: Vuori Favorites + Size Guide

You could top this look with a puffer coat similar to the one below for colder days.

I think Varley is making great, on-trend puffer coats this season.

Slip Skirt + Blazer

For a winter weekend night out, I love the juxtaposition of a feminine slip skirt with a structured blazer.

Faux Leather Pants and a Cropped Jacket

Perfect for evenings out in winter I love a faux leather trouser with a cropped jacket. Then just top the above look with a heavier weight wrap coat over it.

These are my favorite faux leather pants. Wearing an 8.

Travel-Ready Winter Outfit Formulas

Trousers + Converse

A go-to day to day look for me in winter is a favorite pair of trousers. It’s also one I repeat often for travel days. 

I’ll often wear trousers with Converse sneakers but also ballet flats. 

Here’s another take on this winter travel outfit formula. 

Wearing the Sezane Betty Jacket (size L) and the Artizia Effortless Pant (size 8 – recommend sizing up!)

Matching Knit Set

For winter travel, a knit set of separates is great for re-mixing and re-matching once you’ve arrived in your destination.

This set from Kilte blew away my expectations. It’s way more luxe in person and oh-so-comfy and yet put together. Wearing a size 2.

Wearing with my fav Adidas Gazelle sneakers. 

Printed Silk Pants + Oversized Knit

These Toteme patterned silk pants are perfect for airplane travel. Like pajamas but still elevated and beautiful. Wearing size 36.

Seen worn with Adidas Gazelles and my favorite oversized crewneck from Jenni Kayne (size S). Code MEGHAN10 for 10% off.

What to Wear to Work in Winter

A Neutral Color Palette

I love mixing and matching neutrals in the Winter. Ivory, camel, black and even gray all pair beautifully together and are such a cozy and warm way to pair an outfit together.

I especially like a sweater with some texture for a look like this. Abercrombie has a great one at the moment.

Mini Skirt + Riding Boots

Another way to style a pair of riding boots – I love pairing my favorite knitwear with a mini skirt and riding boots for days with meetings but plans at night, too. I always find great skirts at Mango.

Don’t forget a good pair of tights with this look!

Knit Midi Skirt

If you prefer a longer skirt length, try a tea length midi skirt in a heavier knit for a chic statement. Me + Em always has great ones.

Plaid Coat and Black Jeans

When you’re bored of neutral coats, a plaid coat can be such a nice palette cleanser. Abercrombie and Sézane have good options. I usually pair mine with a pair of black jeans and boots. 

Black and Gray Color Palette

Another color combination I love in the winter is black and gray. 

A wool blazer truly is such a versatile piece to own for Winter. I love that it’s part outerwear. Here’s another way I’ve styled mine. With a gingham wool mini skirt and knee high boots with a preppy polo sweater.

or, pair it with a suede skirt. I also love a sweater with extra long sleeves like the one styled above.

And another way. With straight leg jeans, loafers with sheer socks and an oversized button-down.

Casual Everyday Winter Outfits

Wool Blazer

When I don’t need something full length, a wool blazer (size down in this one!) paired with a cashmere scarf does the trick.

Sherpa Coat

Cozy and stylish, I love the juxtaposition of pairing a casual sherpa coat with a dressier boot. 

Brown + Black

I know some people are anti-this color combo of wearing black with brown but I personally think it’s really stylish when done well. 

Wearing a Bottega Bag and Margaux suede boots.

And just a friendly reminder to spray all your suede shoes before winter with a suede protectant spray. They’ll last a lot longer and you won’t have to worry about marks or damage. 

Related: My Favorite and Most Worn Shoes + How I Take Care of Them

Baseball Cap

When I don’t want to wear a beanie, a baseball cap is one of my favorite winter accessories!

Lug Sole Boots

My favorite lug sole boots are water resistant which makes them exceptionally handy during rainy and snowy winter days. I pair mine with my favorite pairs of jeans that hit right at the top of the boot shaft.

I loved the brown suede so much I also got the black leather and espresso suede. These are super lightweight, too which makes them great for winter trips. 

I also think lug sole boots look super cool when paired with a big, oversized leather jacket. 

Or, here’s another way I have styled my lug boots:

. . .

Below I have curated a variety of items from brands I love – and many pieces I own myself and are seen above – if you’re shopping for some new pieces to add to your winter wardrobe. These pieces are versatile and will no doubt help you as you put together winter outfit ideas this season!

Shop Winter Outfit Pieces

 

Hope this helps you guys as you get up, get dressed and get out the door! For even more seasonal finds check out my Fall-Winter Shop. I also have more shopping edits and winter outfit ideas publishing over on my Substack The Noteworthy Edit.

Do you have a favorite look from the above? Would love to hear in the comments below. 

You May Also Like:

• My Favorite Coats for Winter.
• How To Style Sweater Dresses.
• The Best Shoes to Own for Fall and Winter.

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