Madewell makes many of our favorite wardrobe staples — like jeans, work bags, work pants, and flats. And while you can often find select items on sale, there are only a few times a year everything at the brand is discounted. Right now, the Madewell Insider Event is one of those times. The entire site is 25 percent off for Madewell Insiders (it’s free to become one), including already-on-sale items. It’s a good time to get items that rarely go on sale, like shoes and bags, but it’s also a good time to score an extra-deep discount on any clearance winter styles you’ve been eyeing.
Below, I’ve rounded up all my top picks from the sale, grouped by gender and category. I’ve included any products we stand behind, like our favorite relaxed-fit jeans for men and a pair of mary jane flats akin to socks, but I also perused the new arrivals and called out a few favorites. The sale runs through March 23, but sizes will sell out fast, so shop sooner than later.
Women’s fashion and accessories
Women’s tops
Our best vintage-inspired black tee is now under $20. Fashion and e-commerce editor Megan McCarty says it’s “easy to wear, easy to clean, and easy to layer,” and its rich black color hasn’t budged after multiple washes.
Madewell’s Softfade cotton tee is one of the softest shirts Strategist writer Mya Gelber tried on her hunt for the perfect white tee.
Of all the new arrivals at Madewell, I particularly like this versatile and laid-back top.
I’m a sucker for color-blocking and, therefore, this oversize button-up. It’s made from 100 percent cotton poplin, so it’ll work in warmer weather, too.
An airy balloon top that’s actually flattering. It’s $66 in most colors, but if you want something bright, it’s just $52 in a nice marigold-yellow shade.
Women’s bottoms
The jeans a stylist recommends to all of her clients, now in a wide-leg crop style (which happens to be our favorite pair of plus-size jeans and jeans for tall women).
One of our favorite pairs of jeans, particularly for tall women. As someone who’s five-foot-eight, that 32-inch inseam is music to my ears. Price and sizing vary by color, so be sure to check out all the options.
Strategist managing editor Kelsie Schrader says she wears her Emmett jeans no less than twice a week because they’re comfy and work well with nearly any kind of top.
Two Strategist staffers already purchased the garment-dyed version of one of our favorite jeans for petite women. It’s the first time they’ve gone on sale since they came out.
One of our favorite pairs of work pants, backed by Victoria Justice and many a Strategist staffer, is nearly 70 percent off right now, which is just about the best deal you ever see on them.
A reliable pair of shorts to wear all summer.
If you like your denim shorts on the longer side, this now-$30 pair is a good bet.
Women’s skirts and dresses
I don’t even wear skirts, but at $60, this classic satin maxi slip is making me think twice.
A simple sculpted square-neck midi for your summer rotation.
This adorable minidress is also available in black, but this green shade is my favorite.
The bubble hem dominated 2024, and it’s still going strong in 2025.
Women’s outerwear
A comfortable, all-season jacket that you can wear by itself in the spring or layer in the fall.
Madewell’s leather rarely goes on sale. My pick: this luxe, oversize leather blazer.
The opposite of a tight, restrictive jean jacket.
A work blazer for $60 and in stock in sizes 00 through 8 is a true rarity.
Women’s shoes and accessories
Flexible leather plus cushy padding equals an excellent ballet flat. Content creator Ella McFadin says these flats are so comfy, they “feel like socks on your feet.”
A nice, simple, slightly dress-up summer shoe.
If you’re looking for a replacement for the now-discontinued Transport Tote, the Essential Bucket Tote is the next-best thing (and a favorite of Mya Gelber). It can hold a 15-inch laptop, and the long strap is the perfect length.
The shoulder-bag version of this handwoven tote was immediately popular and has already sold out in almost every color. But you can still get it in every color in this larger tote size.
A shoulder bag that can actually hold all your essentials.
Men’s fashion and accessories
Men’s tops
Men’s styles rarely seem to be on sale at Madewell (and when they are, sizing is limited), so right now is really the best time to shop. If you just want to replenish your T-shirt collection, go with our best-in-class less-expensive mid-weight tee, which is now over 40 percent off.
There are plenty of dressier men’s shirts in the sales bin, too. I particularly like this classic camp-collar shirt, which comes in three striped patterns.
Strategist associate editor Jeremy Rellosa recently bought this hoodie and says he’s already worn it too many times to count. He says it’s “soft and not too heavy or thick, but not so light that it doesn’t insulate.”
Men’s bottoms
The only pair of relaxed-fit jeans that won’t make you look like a toddler.
If you prefer a tighter fit, the 1991s are also available in a tapered straight-leg style.
A very versatile pair of trousers from Madewell’s “Milled in Italy” collection.
Men’s outerwear
Men’s accessories
A neutral pack of cushioned socks, now less than $9 each.
’Tisn’t the season, but ’tis a very good deal on a simple beanie.
The Strategist is designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the best acne treatments, rolling luggage, pillows for side sleepers, natural anxiety remedies, and bath towels. We update links when possible, but note that deals can expire and all prices are subject to change.
