30 Best Madewell Insiders Sale Deals 2025

As a shopping writer, I see hundreds (if not thousands) of fashion deals a week — from resort-ready styles to comfortable walking shoes. I take pride in discerning which sales are actually worth shopping because, let’s be honest, the internet is overflowing with deals.

So, trust me when I say that Madewell’s Insiders Event is not one to miss. Through Monday, March 24, Madewell Insiders can snag 25 percent off the entire website, which means that the sale section is double-discounted and already-marked-down pieces are now sporting jaw-dropping prices (think high-quality jeans, spring dresses, best-selling tops, and more up to 80 percent off).

I’ve searched through over 1,400 sale styles to find the 30 best spring fashion finds in Madewell’s sale section during the Insiders Event. Not a Madewell Insider? It’s not too late to join the loyalty program: Just sign up with your email to unlock all the savings at checkout.

Best Top Deals

If you’re looking to refresh your travel wardrobe, high-quality basics and blouses are natural places to start. Madewell is overflowing with deals on versatile tops that you can wear while vacationing, running errands, and everything in between. Shop relaxed, smart styles like the Easy Y-neck Button-up Shirt and V-neck Long-sleeve Top, or go casual with the Relaxed Long-sleeve Raglan Tee and Cotton Perfect Crewneck Tee. Your new favorite tops start at just $25, below. 

Sleeveless Boatneck Side Slit Tee

Elevated basics are key to a sophisticated travel capsule wardrobe. This tee is designed with unique details, like the refined boatneck neckline and side slits. Plus, the cotton-blend fabric is constructed with a bit of stretch, so you’ll stay cozy from the plane to dinner.

Best Bottom Deals

Madewell jeans hardly ever go on sale, but the Insiders Event is your chance to get a pair of the popular denim starting as little as $50. You can also stock up on this season’s pants, shorts, and skirts. Best-sellers like The ‘90s Straight Jean, The Harlow Wide-leg Jean, and the Satin Maxi Slip Skirt are all marked down. Shop my top picks for must-have spring bottoms, up to 66 percent off. 

Superwide-leg Jeans

Wide-leg jeans aren’t going away any time soon. Embrace the trend with this pair that looks refined rather than schlumpy. They can be paired with boots, sneakers, or sandals — and with a 100 percent cotton fabric, they’ll mold to your body and feel more comfy over time.

Best Spring Dress Deals

With the weather finally warming up, I’m adding a few of these dress styles to my cart. Join me in checking out these spring dress deals, up to 80 percent off. These dresses might be timeless, but they’re still up-to-date with 2025 trends: Embrace polka dots with the Smocked-waist Midi Dress, denim with the Denim Seamed Mini Dress, and White Lotus-ready maxis like the Sheer V-neck Dolman Maxi Dress.

Bubble-Sleeve Smocked Mini Dress

This dress features the biggest markdown we’ve seen — and one reviewer even called it the “best little black dress ever.” The chiffon fabric is airy enough for warm spring days, with a smocked waist that accentuates while adding intrigue to the classic silhouette. Add it to your suitcase and wear it day or night for any occasion.

Best Shoe and Accessory Deals

Madewell’s accessories are always worth shopping, but with discounts up to 68 percent off, you’d be remiss to pass up on these styles. Shop best-sellers including The Essential Bucket Tote, The Elsie Mary Jane Flat, and The Essential Convertible Top Handle Crossbody Mini Bag while they’re on rare (and, frankly, major) sale. 

The Essential Bucket Tote

You’ve probably spotted this tote in the office, on vacation, or maybe even on Katie Holmes. It features a timeless shape that suits just about any occasion. Plus, it’s spacious enough to fit your sunscreen, beach read, and emergency umbrella — or your laptop, for those days before your next Out of Office email signature.

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