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14 Fall Fashion Staples For Anyone Who Loves To Be Comfy

  • Kara
  • September 21, 2021
  • Contains Affiliate Links

Today during my morning walk around Golden Gate Park, I was delighted to find fallen crunchy leaves to step on. The fog has been hanging low lately and I’m all here for the moody fall vibes.

It’s the time of year to tuck away summer dresses and pull out all my cute fall outfits to wear. I have fashion staples that I love and wear year after year all through fall and into the winter. I prioritize being comfortable while still looking put together. I’ve worked from home now for over 4 years and know all my basic fall clothes have to make me feel great and ready to tackle the day (even if it’s all from my couch.)

That’s why I’m always on the hunt for timeless cute fall fashion pieces that don’t pinch or squeeze. That’s why I love these new joggers I’m wearing in these photos – no pinching, they look great dressed down with slippers or up with a sweater and Everlane flats.

Since I know so many of you value comfort and style I put together my ultimate autumn wardrobe staples list of all the pieces I have in my closet (or ordering this year to restock worn-out gems) to carry me through to Christmas.

14 Staples For Cozy Fall Fashion Outfits 2021

The best of 2021's comfy fall fashion staples that I wear on the couch or out to brunch. All my favorite cozy fall outfits for the year.

Everlane Leather Day Glove

Photo Credit: everlane.com

White sneakers are my go-to for summer, but when fall rolls around I'm reaching for a white shoe that's more elevated for the fall season. Enter: the Everlane Day Glove. Super comfy, high quality so it'll last for many fall seasons to come and goes with almost every outfit.

Pro tip: size up on this.

Quilted Jogger Sweatpants

Photo Credit: madewell.com

Holy heck, these jogger straight-leg pants seriously make me feel like I'm living in a cloud. It's an elevated style of sweater pants that I can wear on the couch as I work, but are nice enough to take out in the real world.

Cozy Knitted Sweater

Photo Credit: goodnightmacaroon.com

I probably own too many knit sweaters at this point. Wool and knit sweaters are my wardrobe essentials all year round since I live in San Francisco, but especially in the fall. This cozy orange sweater is my favorite one of the 2021 season.

Themed Fair Isle Sweater

Photo Credit: modcloth.com

On top of standard cozy sweaters, I adore all my themed Fair Isle sweaters I have. I mean, these are just so fun for photos and zoom meetings!

Demin Overalls 

Photo Credit: madewell.com

My top fall outfit essentials always revolved around overalls. Blue jeans or skinny jeans pinch my curvy frame, but overalls are SUPER comfy and can be worn with sweaters or cardigans!

Soft Cropped Tee

Photo Credit: madewell.com

I have this extra t-shirt and it's so dang soft and comfy. I pull it out every fall and winter to pair with leggings or under overalls. Sometimes I even wear it to bed!

Oversized Sweater Dress

Photo Credit: goodnightmacaroon.co

They feel like I'm wearing a blanket. That's it. That's the whole reason to get one.

Other great stores to find great sweater dresses are Nordstrom or Amazon!

Black Fedora Hat

Photo Credit: lulus.com

One of my favorite fall wardrobe staples is a black fedora hat that pairs perfectly with dresses, tights and boots. Plus, it keeps my head warm!

Midi & Maxi Dresses

Photo Credit: anthropologie.com

My favorite dresses in the fall are the long midi dresses or maxi dresses that are comfortable on the couch but chic enough to take outside. They pair so well with tights and boots on chillier days!

Trench Coat

Photo Credit: everlane.com

I'm not a black leather jacket kind of girl. Instead, I'll opt for a timeless trench coat like this one that simply goes with everything. (Or a puffer jacket if I'm hiking.)

 Chelsea Rain Boot

Photo Credit: madewell.com

I swear by this exact pair of Chelsea rainboots. The soles are so soft (yet sturdy) so I can wear them all day even if it's raining buckets.

Laceup Boots

Photo Credit: nordstrom.com

A good pair of lace-up leather boots (or faux leather) are KEY for fall. I wear them with dresses, skirts, leggings - anything and all day every day. They're comfy, sturdy and go with all my outfits.

Girlfriend Leggings

Photo Credit: girlfriendcollective.com
  • Girlfriend Collective leggings are my FAVORITE, for any season but especially in the fall season. You can dress them up to down. Pair with Leopard Print booties and that sweater dress for a cute fall look, or that cropped tee and a trench coat for something more timeless. 

Halloween Pajamas

Photo Credit: oldnavy.com

I'm such a sucker for themed pajamas. They always make me smile! I'll be wearing pumpkin or ghost pajamas all October

So many cute comfy fall outfits ahead! I’m ready to say goodbye to summer and hello to cold days paired with hot apple cider. 

More Outfit Ideas & Fall Vibes You’ll Love:

  • Fall Aesthetic 101: From Recipes To iPhone Wallpapers
  • Homemade Pumpkin Spice Syrup For Coffee
  • My Favorite Fall Sweaters Under $50
Kara

I'm the founder of Whimsy Soul (this blog you're reading!) I'm a type 3 enneagram cat lady who lives in San Francisco and loves to find everyday magic to share with others. You can probably find me hunting down hot springs with girlfriends, kayaking, cooking with my husband, petting strangers' dogs or watching like, all the things on Netflix. Follow me on Instagram for even more inspiration!

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