Mark your calendars: the Madewell Insiders Event ends September 27. Until then, Insiders get 25% off everything (well, almost everything—sadly, cashmere is excluded). Plus, get an extra 40% off sale items like these Ashley Ruched Loafers ($84).

Nearly every fashion person I know is signed up for the free Insider program to earn the benefits, i.e., 25% off the buzziest new arrivals. As a Madewell member myself (and a fashion editor looking for an affordable way to revive my fall wardrobe), I popped into my local store to try on some incredibly chic outfits, all for under $483.

I styled new-in sweaters and blouses plus fall staples like corduroy trousers and checkered flannels. I doubled down on accessories—think calf-hair zebra-print ballet flats, plaque-buckle belts, and silk scarves. I embraced the denim-on-denim trend I've been spotting on NYC sidewalks and chic French women lately. And I left with a few goodies to revive my closet.

Scroll on to see the four outfits I styled and shop the best of the Madewell Insiders Event. Happy savings!

The Madewell Insiders Sale Event 2026

1. Double Denim + Plaque Buckle Belt + Glove Flats

First up: a Canadian Tuxedo. I styled the denim shacket over a ringer T-shirt, tucked it into bandana-patchwork jeans, and cinched the baggy look with a plaque-buckled belt. I always lean a little Western come September. Maybe it's the changing leaves that causes this sudden craving for denim on denim. Whatever it is, it looks chic, and right now, it's on discount.

2. T-Shirt + Crewneck Sweater + Satin Pants

It girls would approve of this look. A pop of color draped over my shoulders in the form of a 100% merino wool crewneck, a perfectly oversize white T-shirt, satin trousers with a silk scarf tied around the waist, and a touch of animal print with calf-hair zebra flats.

3. Checkered Flannel + Tan Jeans + Suede Loafers

I've noticed fashion people are wearing more than one button-down, either going for a double-collar look or tying one around the waist (which is what I decided on here). Whatever you choose, make sure it's the Easy Shirt from Madewell. As the name suggests, this 100% cotton shirt is easy to style. I especially like it with the Low-Slung Baggy Jeans and Ashley Ruched Loafer.

4. Ruffle Blouse + Corduroy Trousers + Ankle Boot

No fall outfit guide is complete without a corduroy look. The textured trousers shine when worn with a ruffled blouse and suede accents. I'm thinking of going back and picking up the Idris Ankle Boots. Oh, and don't forget to color-match with burgundy accessories.

The common denominator of my fall mood board, amid cutouts of Carolyn Bessette Kennedy and '90s Calvin Klein runway looks, is sleek suede. Whether in an espresso-colored blazer or a sable miniskirt, I can confirm this luxe-looking textile will be present in my fall wardrobe in more ways than one. And it won't be just me. Gigi Hadid has already been spotted wearing a pair of suede shoes at the airport, and Selena Gomez is known to wear the trend too.

Truth be told, my suede collection could use a refresh. Perhaps a new pair of flats, a tote bag, or even a belt—all at an affordable price, of course. With a strict budget of $200, I curated an edit of the richest and chicest-looking suede items for fall. Scroll on to shop everything from capris to sneakers to trench coats.

Shop the Chicest Suede Finds Under $200

Get ready, people. The big Madewell sale is officially live! Insiders get 25% off almost the entire site (with limited exclusions). All you have to do is sign up for the free Insider program to get the discount. I know fashion people shop this sale because items like this gorgeous leather jacket are discounted.

I scrolled through the new fall arrivals to curate an edit of the on-sale Madewell items I know stylish people (including my colleagues at Who What Wear) would be into. I mean pieces like gorgeous knits, directional jackets, cool denim cuts, and more. Happy shopping.

I read each of Cazzie David's essay collections as soon as they came out—No One Asked for This in 2020 and Delusions this past March—and loved both (I already can't wait for the next one). Since her latest release, she celebrated with a party thrown by AirMail, launched a Substack, and worked with Paloma Wool on a photo series, among other things.

This week in particular, she's been busy: she was seen at New York Fashion Week (including the Proenza Schouler show), attended the U.S. Open, and debuted as the star of Madewell’s new fall denim collection.

In the campaign video, written by Cazzie and her writing partner, Elisa Kalani, she takes on the role of "the denim expert you didn't know you needed." When asked how you know when you've found "the one," she shares the advice: "You'll just know. They'll lift you up. You'll reach for them every day, and miss them when they're not around." This is in reference to jeans.

The full capsule is available now in stores and at Madewell.com, and customers can even call her denim hotline at 1-844-DENIM55 to leave a question.

Below, I spoke with Cazzie about the collaboration, her personal style, and a few of her beauty staples.

What makes you a denim expert?

If I told you I had spent 30 years studying art history, you might say I’m an expert in that field. So technically, I’m an expert at wearing jeans, as I have 30 years of experience. I am also an expert at having anxiety and watching TV.

What’s your go-to style of jeans right now?

I’m reaching for two right now, which are basically opposites. The Low-Rise Loose Jean has a relaxed straight leg and is great if you’re like me and don’t like being restrained by clothing. The Relaxed Bootcut Jean if I am going out and want to show off a particular asset.

How would you describe your personal style in your own words, and what outfit formula do you find yourself repeating over and over? What are some wardrobe staples you can’t live without?

I tend to have one outfit that I repeat over and over until everyone in my life has seen it multiple times and I can’t get away with wearing it anymore. But you can always get away with jeans and an easy T-shirt and sweater. I don’t like to draw too much attention with what I’m wearing but I always like it to feel balanced.

Any trend—or anti-trend—you’re noticing in LA right now? What’s a trend you’re loving right now, or one you predict will be big this fall?

I have to admit I am loving the move away from leggings. Like why are they so tight it never made sense.

Do you have a go-to makeup routine? What are your staples?

I use a little bit of the Kosas brightening concealer, Merit blush in “Cheeky” and don’t leave the house without grabbing five different Clinique black honey dupes.

Shop Cazzie's Favorites

Living on the East Coast, Labor Day Weekend isn't just about cookouts and catching a match at the US Open, but also about the end-of-summer sales. Inspired by my fellow shopping editor Chichi Offor's guide to the best Labor Day sales, I curated an edit of the chicest LDW deals across multiple retailers, focusing on what fashion people are already shopping for this fall. Spoiler: cropped trench coats, raglan T-shirts, oxblood loafers, striped crewnecks, and corduroy trousers are in.

Before we get into the 32 buys, here's a rundown of the deals up for grabs. Save up to 50% at Nordstrom's summer end-of-season clearance until September 7. Use code LONGWEEKEND at Madewell for up to 50% off now through September 8.

But wait! There's more... COS is offering a generous 30% off select items. Enter code MNG30 at Mango and save 30%. Last but not least, earn 40-60% off at Gap's Labor Day Event. I'm aware this can feel daunting, so ahead is a list of editor-approved LDW picks hand-selected by me. You'll find houndstooth blazers, woven totes, '90s-inspired jeans, and so much more. Happy saving!

Labor Day weekend is officially here. If you're like us editors here at WWW, you've been gearing up for one of the biggest shopping sales holidays of the year. Many top-tier retailers are heavily discounting a range of chic fashion finds. Since these huge retail moments can be a bit overwhelming, I've highlighted a handful of must-shop sales below.

Yes, you read that correctly. I've narrowed down all the sales to a handful of the best of the best and included all the details along with a few shopping recommendations from each retail website. Ahead shop picks from J. Crew, Madewell, Nordstrom, Anthropologie, and so many more. Keep scrolling to uncover the best Labor Day weekend fashion deals today.

Shop the Best Labor Day 2026 Sales

Nordstrom

Date: 9/3-9/7
Details: The summer end-of-season clearance sale is here, and shoppers can take up to 50% off.

J.Crew

Date: 9/3-9/7
Details: Take 40% off regular-priced items and an extra 40% off sale items.

Madewell

Dates: 8/28-9/8
Details: Enjoy up to 50% Off Sale During the Labor Day Event. Use Code LONGWEEKEND

Anthropologie

Date: 9/2–9/7
Details: Take up to 40% off clothing and accessories, and take up to 40% off home — including furniture, décor, candles, bedding, and more.

Mango

Date: 9/2-9/7
Details: 20% off when you spend $230

COS

Date: 9/3-9/7
Details: Take 30% off selected pieces.

Uniqlo

Date: 9/4-9/10
Details: Labor Day Sale

Gap

Date: 9/2-9/8
Details: 40–60% Off Select Styles

Old Navy

Date: 9/3-/7
Details: Shop 50% off all jeans, tees, sweatshirts, and hoodies

As a frugal shopper, when my favorite brands have a sale, I genuinely can’t stop myself from checking them out. I’ve been very good with my self-control, but Madewell just put a bunch of chic items on sale. Fall is just around the corner, and if you’re ready to shop for the season, this sale is right up your alley.

In the mix, I’ve compiled an array of trendy items and elevated basics, from lightweight jackets to sweaters; these finds are perfect for the upcoming season. The best part about each find: They’re all so versatile. You can create a myriad of outfits with any one of them. Fall is all about experimenting with staple pieces and maybe even building a capsule wardrobe, and what better way to expand yours than with a seasonally-appropriate sale? Madewell’s Labor Day Event is up to 50% off of each item, and you can get an extra 30% off with the code LONGWEEKEND, so keep scrolling to shop my top picks.

Shop Madewell's Labor Day Sale

There's no denying that Fall is right around the corner. Ahead of the soon-to-be decreasing temperatures, my fellow WWW editors and I will be dedicated to getting you ready for the seasons ahead. With that in mind, I took a browse of all the latest arrivals from Madewell and J.Crew. I came across several pieces worth taking a look at. Don't worry. I included my shopping editor-approved curation of the best new arrivals from each below.

In the mix, you can expect a range of versatile yet on-trend items. Whether you need new pairs of jeans, fun pant options, cute tops, and even cool shoes and accessories, look no further. Keep scrolling to uncover my favorite new arrivals. I bet it's seriously impossible to leave empty-handed.

Shop Madewell New Arrivals

Madewell's newest arrivals are so impressive. In particular, the new Greta flats' color ways are so cute. Stripes are having a huge moment. Check out the Easy Shirt, Boatneck Rugby top, and this 100% Cotton sweater if you're as obsessed with the pattern as me. Overall, there are numerous wearable yet aesthetically pleasing options to choose from.

Shop J.Crew New Arrivals

Don't be afraid to mix and match some of these fun pieces. Some pieces to pay attention to include: these cool lace-trimmed shorts, the Verona ballet flats, this pretty barn jacket, and so many cute yet trendy basics.

Listen. I am an avid pant wearer. You might even call me a bit of a tomboy. I'm just a fashion person who really appreciates function and comfort over looking trendy. That said, I've never been much of a skirt or dress person, but with time and more comfort in my body, that's starting to change. While on my daily sweeps of fashion sites, I keep coming across skirts that have helped me see the light about wearing them more often. I know slipping one on to style an outfit around is so fun, and I want to partake in that more often.

All the chic skirts I've found have been from the same three sites: Zara, Madewell, and J.Crew. Each retailer is different in aesthetics, but they all have one thing in common, an affordable price point. If you're in the same boat as me, trying new trends and items when you're already unsure about them is only more difficult if it's expensive. However, I'm in the camp of finding fashion items that are expensive looking. This is definitely why these skirts have changed my mind. Gone are the days of constantly wearing pants in the summer. Keep scrolling to shop 30 of the best skirts that won't break the bank to wear this summer from Zara, Madewell, and J.Crew.

Zara

From asymmetrical plaid skirts to simple bias-cut satin skirts, each selection is absolutely fabulous and budget-friendly. Zara is the ideal place to turn when you need ultra-luxe, runway-eque clothing for a fraction of the price. I've discovered other shapes, from a classic A-line shape in a rich blue to wrap skirts fitting for an elegant dinner. Keep scrolling to find the best one for you.

Shop Zara Skirts

Madewell

Madewell is the best place to shop for simple style pieces, from midi skirts to classic denim skirts. I've always been drawn to minimalist pieces to style, and this brand has always come through. Other styles include a casual drawstring skirt, a maxi slip skirt, and a woven miniskirt. Whether you need some staple pieces or want to experiment ever so slightly, Madewell is the best place to find the chic skirt that fits your personal style.

Shop Madewell Skirts

J.Crew

J.Crew is the unsung hero in many of our closets. If you haven't been privy to shopping there, I highly recommend pursuing the site for everyday staples. While scrolling through the site myself, I found an array of skirts in vacation-worthy prints, a wrap-style skirt, and a miniskirt with eye-catching embellishments. Shop all my chic finds below.

Shop J.Crew Skirts

While most people might cringe and shudder at '80s fashion making a comeback in 2026, there's one retro trend rearing its head that fashion people are fans of. No, it's not oversize costume jewelry or shoulder pads. Striped jeans are having a major moment this summer. From pinstripe varieties loved by Ayo Edebiri to the bold and colorful pairs Spanish women are wearing, striped jeans are poised to be this season's biggest denim trend by far.

Although I can't say I predicted it, personality-first denim is having a moment. Printed jeans, embellished denim, colorful washes, and pastel pairs are all signaling the fashion set's move toward fun, bright, funky denim ahead of the new season. Ahead, see how the coolest people on Instagram are styling their striped jeans along with the best pairs to buy and more must-have summer items featuring this rising print trend.

See More of Summer 2026's Striped-Jeans Trend

Striped Jeans on the Style Set

Shop Striped Jeans

Shop More Summer Stripes

My friends and I are in the midst of planning a summer getaway. Where to? We don’t know. I’ve floated Newport, Rhode Island, to see its Jazz Festival, or even Nantucket and Martha’s Vineyard. But wherever we end up, the dress code is East Coast chic. That means lots of linens, summer whites, colored jeans, and nautical stripes. Thankfully, Madewell has plenty of goodies that fit the bill.

I'm counting on Madewell to supply all my summer 2026 accessories. I'm talking crochet flats, thong sandals, woven totes, and silk bandanas. I'll be wearing them with linen trousers and a lace-trim top. Keep scrolling to shop all 22 items my friends and I are eyeing for our upcoming getaway. Hopefully we'll decide on a destination as easily as it was to add to cart.

Shop the Best Madewell Finds for Summer 2026