Update Consent

Best Madewell Winter Sale 2020-2021

Madewell's Winter Sale Has All the Fashion Trends We Love

As POPSUGAR editors, we independently select and write about stuff we love and think you'll like too. If you buy a product we have recommended, we may receive affiliate commission, which in turn supports our work.

With the new year around the corner, it's officially time to take stock of our closet and decide what stays and what's worth investing in. So many retailers are having end-of-year sales, which makes it easy to tap into new trends (or stock up on affordable wardrobe classics) while staying within budget.

Madewell's winter sale has all the cool trends we're eyeing for 2021, including lug-sole boots, quilted coats, and easygoing matching sets. To get you started on your shopping, I've rounded up over 50 exciting options, ranging from fail-safe winter layers to everyday pieces you'll lounge, work, and sleep in.

Image Source: Madewell

Boxy Workwear Shirt

Boxy Workwear Shirt ($55, originally $75 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Boxy Workwear Shirt
$55
from madewell.com
Buy Now

Ribbed Wool Neck Warmer

Ribbed Wool Neck Warmer ($32, originally $45 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Ribbed Wool Neck Warmer
$32
from madewell.com
Buy Now

Heart Chunky Huggie Hoop Earrings

Heart Chunky Huggie Hoop Earrings ($10, originally $24 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Heart Chunky Huggie Hoop Earrings
$10
from madewell.com
Buy Now

Tie-Dye Newville Tee

Tie-Dye Newville Tee ($40, originally $55 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Tie-Dye Newville Tee
$40
from madewell.com
Buy Now

Watch This!

Pop Quiz

Watch the Cast of Fear Street Play a Creepy Game of Horror Movie "Would You Rather"

Caldwell Double-Breasted Blazer

Caldwell Double-Breasted Blazer ($65, originally $168 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Caldwell Double-Breasted Blazer
$65
from madewell.com
Buy Now

MWL Ribbed Funnelneck Sweatshirt

MWL Ribbed Funnelneck Sweatshirt ($80 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
MWL Ribbed Funnelneck Sweatshirt
$80
from madewell.com
Buy Now

Belgrave Sunglasses

Belgrave Sunglasses ($65 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Belgrave Sunglasses
$65
from madewell.com
Buy Now

(Re)sourced Cashmere Ribbed Henley Sweater

(Re)sourced Cashmere Ribbed Henley Sweater ($115, originally $158 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
(Re)sourced Cashmere Ribbed Henley Sweater
$115
from madewell.com
Buy Now

Flannel Flap-Pocket Oversize Ex-Boyfriend Shirt

Flannel Flap-Pocket Oversize Ex-Boyfriend Shirt ($88 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Flannel Flap-Pocket Oversize Ex-Boyfriend Shirt
$88
from madewell.com
Buy Now

Caldwell Double-Breasted Blazer

Caldwell Double-Breasted Blazer ($115, originally $168 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Caldwell Double-Breasted Blazer
$115
from madewell.com
Buy Now

Vegan Leather Chore Jacket

Vegan Leather Chore Jacket ($150, originally $198 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Vegan Leather Chore Jacket
$150
from madewell.com
Buy Now

Sherpa Chestnut Jacket

Sherpa Chestnut Jacket ($100, originally $150 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Sherpa Chestnut Jacket
$100
from madewell.com
Buy Now

The Alex Loafer

The Alex Loafer ($100, originally $158 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
The Alex Loafer
$100
from madewell.com
Buy Now

The Rosie Ankle Boot

The Rosie Ankle Boot ($100, originally $178 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
The Rosie Ankle Boot
$100
from madewell.com
Buy Now

Striped Tank Sweater Dress

Striped Tank Sweater Dress ($60, originally $90 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Striped Tank Sweater Dress
$60
from madewell.com
Buy Now

Pleated Taper Wide-Leg Pants

Pleated Taper Wide-Leg Pants ($80, originally $118 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Pleated Taper Wide-Leg Pants
$80
from madewell.com
Buy Now

Madewell x Kule Sherpa-Lined Oversize Jean Jacket

Madewell x Kule Sherpa-Lined Oversize Jean Jacket ($140, originally $198 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Madewell x Kule Sherpa-Lined Oversize Jean Jacket
$140
from madewell.com
Buy Now

Sidewalk Low-Top Sneakers

Sidewalk Low-Top Sneakers ($70, originally $88 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Sidewalk Low-Top Sneakers
$70
from madewell.com
Buy Now

Estate Cocoon Coat

Estate Cocoon Coat ($230, originally $328 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Estate Cocoon Coat
$230
from madewell.com
Buy Now

The Carlotta Tall Boot

The Carlotta Tall Boot ($200, originally $298 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
The Carlotta Tall Boot
$200
from madewell.com
Buy Now

(Re)sourced Cotton Puff-Sleeve Tee

(Re)sourced Cotton Puff-Sleeve Tee ($35, originally $50 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
(Re)sourced Cotton Puff-Sleeve Tee
$35
from madewell.com
Buy Now

The Alex Oxford

The Alex Oxford ($100, originally $148 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
The Alex Oxford
$100
from madewell.com
Buy Now

Cashmere V-Neck Sweater

Cashmere V-Neck Sweater ($75, originally $98 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Cashmere V-Neck Sweater
$75
from madewell.com
Buy Now

(Re)sourced Georgette Sheer-Sleeve Smocked Midi Dress

(Re)sourced Georgette Sheer-Sleeve Smocked Midi Dress ($90, originally $138 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
(Re)sourced Georgette Sheer-Sleeve Smocked Midi Dress
$90
from madewell.com
Buy Now

Tie-Waist Midi Dress

Tie-Waist Midi Dress ($80, originally $148 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Tie-Waist Midi Dress
$80
from madewell.com
Buy Now

Elmcourt Coat

Elmcourt Coat ($190, originally $268 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Elmcourt Coat
$190
from madewell.com
Buy Now

Pointelle Mockneck Pullover Sweater

Pointelle Mockneck Pullover Sweater ($75, originally $110 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Pointelle Mockneck Pullover Sweater
$75
from madewell.com
Buy Now

Plaid Flannel Raglan Button-Front Shirtdress

Plaid Flannel Raglan Button-Front Shirtdress ($75, originally $108 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Plaid Flannel Raglan Button-Front Shirtdress
$75
from madewell.com
Buy Now

Striped Evercrest Turtleneck Sweater

Striped Evercrest Turtleneck Sweater ($50, originally $75 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Striped Evercrest Turtleneck Sweater
$50
from madewell.com
Buy Now

Petite 10" High-Rise Skinny Jeans

Petite 10" High-Rise Skinny Jeans ($90, originally $135 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Petite 10" High-Rise Skinny Jeans
$90
from madewell.com
Buy Now

The Oversize Trucker Jean Jacket

The Oversize Trucker Jean Jacket ($95, originally $128 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
The Oversize Trucker Jean Jacket
$95
from madewell.com
Buy Now

Zip-Pocket Coverall Jumpsuit

Zip-Pocket Coverall Jumpsuit ($100, originally $148 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Zip-Pocket Coverall Jumpsuit
$100
from madewell.com
Buy Now

The Perfect Vintage Tee

The Perfect Vintage Tee ($20, originally $40 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
The Perfect Vintage Tee
$20
from madewell.com
Buy Now

The Daisy Platform Mule

The Daisy Platform Mule ($100, originally $158 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
The Daisy Platform Mule
$100
from madewell.com
Buy Now

The Ivy Chelsea Boot

The Ivy Chelsea Boot ($198 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
The Ivy Chelsea Boot
$198
from madewell.com
Buy Now

Dip-Dye Cashmere Shrunken Sweatshirt

Dip-Dye Cashmere Shrunken Sweatshirt ($110, originally $138 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Dip-Dye Cashmere Shrunken Sweatshirt
$110
from madewell.com
Buy Now

Bandana Scarf

Bandana Scarf ($18, originally $35 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Bandana Scarf
$18
from madewell.com
Buy Now

Sherpa McClancy Coat

Sherpa McClancy Coat ($130, originally $275 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Sherpa McClancy Coat
$130
from madewell.com
Buy Now

Chunky Pom-Pom Beanie

Chunky Pom-Pom Beanie ($29, originally $42)

Image Source: madewell.com
Chunky Pom-Pom Beanie
$29
from madewell.com
Buy Now

Whisper Cotton Rib-Crewneck Tee

Whisper Cotton Rib-Crewneck Tee ($17, originally $25 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Whisper Cotton Rib-Crewneck Tee
$17
from madewell.com
Buy Now

Chunky Chain Necklace

Chunky Chain Necklace ($30, originally $38 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Chunky Chain Necklace
$30
from madewell.com
Buy Now

Emmett Wide-Leg Full-Length Pants

Emmett Wide-Leg Full-Length Pants ($70, originally $98 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Emmett Wide-Leg Full-Length Pants
$70
from madewell.com
Buy Now

Highbury Military Jacket

Highbury Military Jacket ($80, originally $135 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Highbury Military Jacket
$80
from madewell.com
Buy Now

Eldridge Zip Coat

Eldridge Zip Coat ($200, originally $228)

Image Source: madewell.com
Eldridge Zip Coat
$200
from madewell.com
Buy Now

The Monica Mule

The Monica Mule ($100, originally $138 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
The Monica Mule
$100
from madewell.com
Buy Now

Ribbed Turtleneck Top

Ribbed Turtleneck Top ($30, originally $50 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Ribbed Turtleneck Top
$30
from madewell.com
Buy Now

Vegan Leather Chore Jacket

Vegan Leather Chore Jacket ($130, originally $198 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Vegan Leather Chore Jacket
$130
from madewell.com
Buy Now

Vegan Leather A-Line Mini Skirt

Vegan Leather A-Line Mini Skirt ($115 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Vegan Leather A-Line Mini Skirt
$115
from madewell.com
Buy Now

Drawstring Midi Slip Skirt

Drawstring Midi Slip Skirt ($40, originally $98 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Drawstring Midi Slip Skirt
$40
from madewell.com
Buy Now

Faux-Fur Crop Coat

Faux-Fur Crop Coat ($160, originally $228)

Image Source: madewell.com
Faux-Fur Crop Coat
$160
from madewell.com
Buy Now

(Re)sourced Georgette Smocked-Neck Midi Dress

(Re)sourced Georgette Smocked-Neck Midi Dress ($80, originally $158 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
(Re)sourced Georgette Smocked-Neck Midi Dress
$80
from madewell.com
Buy Now

Reversible Quilted Liner Jacket

Reversible Quilted Liner Jacket ($130, originally $175 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Reversible Quilted Liner Jacket
$130
from madewell.com
Buy Now

(Re)sourced Cotton Oversized Sweatshirt

(Re)sourced Cotton Oversized Sweatshirt ($48, originally $70 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
(Re)sourced Cotton Oversized Sweatshirt
$48
from madewell.com
Buy Now

Quilted Corduroy Walton Shirt-Jacket

Quilted Corduroy Walton Shirt-Jacket ($120, originally $168 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Quilted Corduroy Walton Shirt-Jacket
$120
from madewell.com
Buy Now

Tomboy Straight Jeans

Tomboy Straight Jeans ($90, originally $128 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Tomboy Straight Jeans
$90
from madewell.com
Buy Now

Reversible Quilted Scarf Jacket

Reversible Quilted Scarf Jacket ($130, originally $185 (plus an extra 30 percent off with code GIGANTIC))

Image Source: madewell.com
Reversible Quilted Scarf Jacket
$130
from madewell.com
Buy Now

Want More?

POPSUGAR Would Like To Send You Push Notifications.