Winter Outfit Ideas

January 22, 2024

We’ve officially reached that time of year where getting dressed is 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 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.

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.

Weekend Casual Athleisure Outfit I wit & whimsy

Weekend Athleisure

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.

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

Best Coats for Women

Paris Winter Outfit

Trousers + Converse

A go-to day to day look for me in winter is a favorite pair of trousers. I’ll often wear trousers with sneakers but also ballet flats

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 sneakers. 

Styling Winter Classics I J.Crew Double Breasted Coat I Cable Knit Sweater and Suede Rag & Bone Boots

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.

Meghan in Paris Winter Outfit Arc de Triomphe

Riding Boots + Wrap Coat

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

Fall Paris Outfit in the Rain - Sweater Dress and Boots

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. 

Plaid Coat and Booties Winter Outfit Inspo

Plaid Coat and Black Jeans

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

Neutral Winter Outfit Inspo

Black and Gray Color Palette

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

Teddy Coat and Kick Flares on Meghan Donovan

Sherpa Coat

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

Sarah Flint Riding Boot

Mini Skirt + Riding Boots

I love pairing my favorite knitwear with a mini skirt and riding boots for days with meetings but plans at night, too. Don’t forget a good pair of tights with this look!

& Other Stories Wrap Coat and Knit Skirt

Knit Midi Skirt

If you prefer a longer skirt length, try a tea length midi skirt in a heavier knit for a chic statement.

Fall Date Night Outfit featuring Faux Leather Pants

Faux Leather Pants and a Cropped Coat

Perfect for evenings out in Winter just top the above look with a heavier weight wrap coat over it.

Larroude Boot France Outfit

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.

Freda Salvador Boot Fall Outfit

Lug Sole Boots

My favorite lug sole boots are waterproof 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.

Neutral Winter Outfit I Striped Sweater

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.

Sezane James Coat

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. 

. . .

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!

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

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comments +

  1. Shirley says:

    Thanks for all of the inspiration! I find this time of year to be challenging for dressing as well and this post is perfect!

  2. Yana says:

    Great post this morning! Love getting ideas (especially for winter) and all of your outfits are gorgeous!

  3. Kate Scott says:

    So many great ones, bookmarking this for the next four months!!

  4. Nancy says:

    See what a positive the shopping freeze can be? Its great to go “shopping” in our own closet every once in awhile. Preferably with the fresh eyes of a good friend (or Amy in my case) and pull out some old favorites we had forgotten about. You look lovely in all of these pulled together looks. Thx for the inspiration Meghan.
    Happy New Year. xo

  5. Libby says:

    OMG this helps so much! Every outfit I tried on this morning, and looked at in the mirror, I would say “too christmasy”, and take it off. This cycle happened multiple times, and was actually quite comical! ahahaha

    xoxo Libby

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