Comfy Fall/Winter OutfitsWhile I have always appreciated a comfy outfit from time to time, the older I get the more I am leaning into an entire comfy wardrobe. LOL I used to have a sweatshirt and maybe a pair of leggings to throw on when I didn’t feel like putting myself together, but that outfit has slowly morphed into an entire collection of clothing that is designed to be comfortable yet still looks super chic. I refuse to sacrifice style for comfort and definitely feel like you can successfully accomplish both in one look.

I have a few brands that are my favorite to shop when I want chic athleisure such as Spanx and Varley, but more than anything I have an easy aesthetic when it comes to my comfy outfits. That aesthetic is matching sets, neutral colors and classic fits which allow me to mix and match pieces easily to create looks that feel put together but don’t sacrifice comfort. If you need some comfy outfit ideas or comfy outfit inspo, this blog post will share a ton of options and exact pieces to get to create your own comfy collection of clothes. (I love me some alliteration! LOL)

15 Comfy Fall/Winter Outfits

Spanx Air Essentials Matching Set

Spanx Air Essentials Matching SetVest | Sweatshirt | Joggers | Sneakers | Bag | Sunglasses

I have a few Spanx Air Essentials pieces and constantly reach for them in my day to day life. The material is insanely soft and there are so many new styles and fits to choose from.

Varley DoubleSoft Half Zip and DoubleSoft Joggers

Varley DoubleSoft Half Zip and DoubleSoft JoggersPullover | Joggers | Sneakers (similar) | Bag (similar) | Sunglasses

If I’m being honest, the material of the Varley DoubleSoft and Spanx Air Essentials is VERY similar which I why I love them both so much. LOL Varley does have a more extensive collection to choose from and their styles are some of my favorite. The fits and color options are incredibly chic yet look polished and refined.

Oversized Tunic and Straight Leg Jeans

Oversized Tunic and Straight Leg Jeans | Comfy Fall/Winter OutfitsCoat | Sweater | Bag | Jeans (similar) | Shoes (similar) | Sunglasses

I know not everyone thinks of jeans as very comfy, but if joggers or sweatpants are out of the question they are the next best option in my opinion. A pair with tons of stretch is my preferred choice and a dark wash with no distressing is easy to wear with anything. This Amazon tunic is one of my all time favorite tunic sweaters and feels insanely soft while also being the most perfect oversized fit. Get one color, get a few – you will not be disappointed.

Varley Freya Sweatshirt and Slim Pant

Varley Freya Sweatshirt and Slim PantVest | Sweatshirt | Joggers | Sneakers | Bag | Sunglasses

With many comfy outfits, lack of shape or definition can create a frumpy and messy look. So I appreciate when sweatshirts like this one from Varley add some shape in the form of a drawstring waist. You can cinch it in as much or little as you want but it adds some interest to the look while also creating a flattering silhouette.

Varley Vine Pullover and Slim Cuff Pants

Comfy Fall/Winter OutfitsPullover | Joggers | Sneakers | Bag | Sunglasses

This pullover from Varley is a best seller for a reason. The details, the oversized fit, the color options – it’s absolute perfection. I have a few colors and wear them ALL THE TIME.  Additionally, I have a few of the slim pants from Varley because while they are a traditional jogger, the slim fit makes them look more polished and chic.

Oversized Coatigan and Straight Leg Jeans

Oversized Coatigan Comfy Fall/Winter OutfitsCoatigan | Henley | Jeans (similar) | Belt | Clogs | Bag | Sunglasses

I’ve raved about this coatigan for two years now and will continue to do so every fall and winter. It’s the perfect mix between a cardigan and a coat, has an effortless drape that never looks sloppy and can be styled a ton of different ways.

Varley Zip-Through Knit and Slim Cuff Pants

Varley Knit and Slim Cuff Pants Comfy Fall/Winter OutfitsPullover | Joggers | Sneakers | Bag | Sunglasses

As someone that runs hot most of the time now that I am in my mid 40’s, I really appreciate a knitted or vented sweater/sweatshirt option. It’s built in ventilation that I can control. LOL I can either layer something underneath it if it gets cold or just wear a nude tank if it’s a bit warmer that day.

Amazon Long Puffer and Matching Set

Amazon Long Puffer Comfy Fall/Winter OutfitsJacket | Pullover | Joggers | Sneakers | Bag | Mittens | Beanie

I have this coat styled two different ways in this post and it’s been one of my favorite Amazon coat buys ever. It feels like you are wearing a puffy comforter yet the fit is still not too bulky. And styling it in an all monochromatic way is one of the easiest options to create a comfy yet still chic looking outfit.

Amazon Matching Set

Amazon Matching SetMatching set | Sneakers

This set is a nearly identical option to the Spanx Air Essentials set but at a much more budget friendly price point. It’s super soft and comes in a ton of different colors.

Spanx Air Essentials Hoodie and Faux Leather Leggings

Spanx Air Essentials Hoodie and Faux Leather LeggingsVest | Sweatshirt | Leggings | Sneakers | Bag | Sunglasses

If I am going to wear black leggings out and about during the fall/winter seasons, it will more than likely be my Spanx faux leather leggings every time. They still are comfy like a regular black legging, but the added sheen gives them an elevated look and creates a nice contrast for my outfit.

Oversized Coatigan and Spanx Faux Leather Leggings

Oversized Coatigan and Faux Leather Leggings | Comfy Fall/Winter OutfitsCoatigan | Sweatshirt (similar) | Leggings | Sneakers | Bag | Sunglasses

Combining two of my favorite fall wardrobe staples in one outfit – my oversized Mango coatigan and my Spanx faux leather leggings. I rewear this outfit all season long switching out the sweatshirt and sneakers for a bit of variation.

Varley Mentone Pullover and Slim Cuff Pants

Varley Mentone Pullover and Slim Cuff PantsSweater | Joggers | Sneakers | Bag | Sunglasses

This Varley pullover is another top seller for them and I can understand why. I have it styled with joggers here but it also looks great worn with trousers or jeans. It’s super cozy yet still looks elevated and chic.

Quilted Jacket and Black Leggings

Quilted Jacket Comfy Fall/Winter OutfitsCoat | Hoodie (similar) | Leggings | Sneakers | Bag | Sunglasses

One of the easiest ways to elevate a comfy casual outfit is by choosing pieces in neutral colors but that still have texture. This quilted jacket in black is easy to wear with almost any look but the quilted pattern adds a bit of interest to your look. Combining that with the sheen of the faux leather leggings makes for a comfy outfit that still looks nicely put together.

Varley Ells Jacket and Black Leggings

Varley Ells Jacket Comfy Fall/Winter OutfitsPullover | Leggings | Sneakers | Belt Bag | Sunglasses

This Varley jacket is nearly identical to the Vine pullover but the zipper goes all the way down so you can wear it as a jacket if you want. I love the super wide color and long length as it hits at the perfect spot to cover my butt but not look too oversized.

Amazon Puffer Coat and Black Leggings

Amazon Puffer Coat and Black LeggingsJacket | Sweater | Leggings | Boots | Sunglasses

This Amazon puffer coat went viral many years ago and I was swept up into the hype immediately. Thankfully the coat exceeded my expectations and it’s still one of my most worn winter coats ever since. It’s SUPER warm and cozy but the added zipper details and quilted style makes it more interesting and can be a great statement coat to wear with leggings and boots.