I'm a Former Madewell Employee, and Even I Can’t Pass Up Its Presidents Day Sale Deals — From $14

Before I dedicated my days to finding the best travel outfits as a full-time shopping writer, I built up my fashion expertise as an in-store stylist for Madewell. Working closely with customers, I mastered finding elevated basics like soft knitwear and comfortable jeans for everything from everyday wear to tropical vacations and even destination weddings. 

Now that my focus has shifted to finding the best online deals, I’m excited to share my picks from Madewell’s Presidents Day sale. It’s an opportunity to stock up on travel-friendly pieces for a fraction of the price — I’m talking up to 87 percent off best-sellers that’ll quickly earn the top spot on your packing list. 

From now until February 21, you score an extra 30 percent off the entire sale section when you use the promo code SALEONSALE at checkout. To help you find the best Madewell Presidents Day sales, I’ve listed my expert picks below for you to shop now before the sale ends.

Best Deals Overall

Oversized Trucker Jean Jacket, $40 (originally $148)
Ardin Ankle Boot, $63 (originally $198)
Satin Sleeveless Maxi Slip Dress, $35 (originally $158)
Harlow Wide-Leg Pant in Drapey Twill, $28 (originally $118)
Ribbed Crewneck Sweater, $14 (originally $110)
Kline Blazer, $70 (originally $238)
’90s Straight Jean, $55 (originally $128)
Essential Sling Crossbody Bag, $77 (originally $148)
Cinched Long-Sleeve Top, $28 (originally $68)
Oversized-collar Peacoat, $126 (originally $328)

When it comes to shopping a Madewell sale, you’re going to want to tackle jeans first because it’s usually the first thing to go. Madewell denim is high-grade, and most jeans are stretchy. They’re the perfect alternative to baggy sweatpants when you travel, letting you deboard the plane and start sightseeing in style. 

Grab these 90s-inspired straight-leg jeans for only $55, and make it a complete outfit with this ribbed crewneck sweater that’s on sale for $14 and is versatile enough to be worn with your coziest joggers or a sleek pair of trousers.

Best Fashion Deals

Whether you’re shopping for a cozy winter escape or tropical beach vacation, the site has a wide array of capsule wardrobe items that let you pack less while still having a variety of outfits. Be sure to snap up pieces that rarely get discounted first, including denim jackets like this oversized trucker style for only $40. 

If you have a wedding coming up, grab this silky sleeveless dress for just $35. It’s sleek enough to fit inside a personal item, and it’s so versatile, you can wear it to the office with a cardigan once the wedding is behind you.

’90s Straight Jean

Satin Sleeveless Maxi Slip Dress

Best Shoe Deals

Madewell isn’t being stingy with its shoe sales either, you can find premium leather boots, loafers, and ballet flats for less than $100. I recommend swiping these over-the-knee boots that are currently 76 percent off, and have a zipper closure that lets you take them off quickly to get through airport security. If you’re on the hunt for a new pair of elevated ballet flats, Madewell’s best-selling pair is on sale for $42.

Ardin Ankle Boot

Corinne Lugsole Loafer

Best Bag Deals

Suitcases aren’t the only bags you need to consider for vacation. A smaller bag is essential for carrying items like your wallet, passport, and sunglasses. Thankfully, Madewell has bags of all sizes on sale, like this sling crossbody bag for $77 that’ll free up your hands while you sightsee, or if you need more space, this medium bucket tote that’s on sale for $105.

Essential Curve Shoulder Bag

The Medium Bag

Best Sweater Deals

You can’t always predict the weather, which is why packing extra layers comes in handy. Madewell’s sweater collection doesn’t just spotlight fashion-forward designs, but its made up of cardigans and pullovers that will keep you warm in style. Some of my favorite picks include this ribbed crewneck for just $14 as well as this wool-blend cardigan that’s versatile enough to be worn alone or layered over a T-shirt for those cool nighttime walks.

Wool-blend Crewneck Cardigan

Ruffle Mockneck Sweater

Best Activewear and Loungewear Deals

Madewell also offers loungewear that’s both polished and comfy — allowing you to dress up your overnight train ride outfit. Each piece can be worn on long rides or for just lounging around the house, giving you snugly tops and bottoms you can wear on repeat. Some of the best loungewear deals you can get now include this mockneck sweatshirt for $35 as well as these $21 soft tapered pants that you can throw on and go without a second thought.

Midweight Mockneck Sweatshirt

Pull-on Tapered Pants

Love a great deal? Sign up for our T+L Recommends newsletter and we’ll send you our favorite travel products each week.