8 Madewell Picks to Wear During the Festive Season

If you have been following me for awhile then you know my love for Madewell runs deep.  And receiving this GIFTED package from them was truly icing on the cake in 2020!  Read on for my 8 Madewell picks to wear during the festive season!

Madewell jeans with a plaid blazer

This is a great time to stock up if you have been eyeing any Madewell pieces!  Many of their best sellers are up to 50% off right now (think sweaters, tops, boots and more)!  Use code VERYMERRY

High Rise Skinny Jeans

Madewell knows jeans.  I started wearing Madewell jeans a few years ago and haven’t looked back.  There are so many styles and the quality is amazing.  I love the look of these, something different with the pieced yoke look – a nod to the 80’s if you will.  They have the perfect amount of stretch too.  I am wearing this pair throughout this post.  

A pullover sweater

Another thing Madewell knows is sweaters.  I mentioned on my IG stories recently that I buy a couple of Madewell sweaters each season.  They always have cute patterns and styles, but their classics like the one below are always a winner in my book. I am wearing the XS.

Women wearing Madewell sweater and jeans

A Plaid Blazer

Just a touch oversized, this blazer gives a professional yet casual look.  Wear it over a bodysuit, or layer it over a tee.  It will be in your closet for years to come.  I am wearing the XS. 

Plaid oversized blazer from Madewell

Gathered Puff Sleeve Sweatshirt

It’s all in the details with this one.  I LOVE the cute subtle puff sleeve on this.  Several colors available too!  I’m wearing the XS.

Women wearing Madewell sweatshirt and jeans

Longsleeve Pajama Set

OH EM GEEEEEEE! These are so fab!  How have I never owned Madewell PJs before?! Grab a pair for yourself OR gift a pair, either way grab a set before they’re gone!  I am wearing the XS.  

Madewell Pajama Set for the holidays

Sherpa Scuff Slippers

Madewell slippers are another well known item.  These classic little sherpa numbers are sure to be a hit this cozy season. 


The Brynn Boot

An obvious BEST SELLER… these square toed, block heeled brown boots will make you feel like you have it all pulled together!  They fit true to size. 

The Brynn brown bootie from Madewell

Plaid Dresses – Madewell Picks to Wear During the Festive Season

Madewell always has great casual dress options.  This super soft flannel with pink accented plaid goes perfectly with the Brynn boot!  You could pair this with a great pair of thicker opaque tights too on super cold days!

Women wearing plaid Madewell dress and boots

Looking for more Madewell?  Check out some of my faves throughout the seasons here!


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This post may contain affiliate links, which means I receive a commission if you choose to purchase through links I provide (at no extra cost to you). As an Amazon Associate I earn from qualifying purchases.



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About Emily

Hi! I’m Emily; wife, mom of two, and all things digital freelance entrepreneur! This is a space where I share my love of all things style, home, family, DIY and more here in Saint Louis, MO. I’m so glad you’re here!

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