I'm a Former Madewell Stylist, and I Think These 11 Staples Work for Everyone


(Image credit: @madewell; Pictured: @waityouneedthis)

Calling all Madewell stans. If you're a fan of the brand's classic, well-made pieces, then you're probably well aware of which perennial staples are the most popular. There are so many things the retailer gets right, from its denim selection to its everyday shoes and classic bags, but above all, there are a handful of key buys that are truly universal.

After years of working as a stylist at the brand, my friend Zoë Thompson is well-acquainted with Madewell's offering, so I had her share the exact pieces that she thinks work for everyone, regardless of your taste, age, or budget. There are 11 of these Madewell basics that she insists are truly versatile, timeless, and work for everyone. Think of these as the kind of items that you'll invest in now and continue to wear on repeat for years to come. Yep, they're just that good. Continue on to read and, of course, shop each of the ones she recommends.

1. The Medium Transport Tote

"I've been in a loving relationship with my Medium Transport Tote for years. It's the smaller and more effective version of Madewell's original best-selling bag, the Transport Tote. This piece is perfect for you if A) you find yourself always losing your phone or your keys in your bag (enter the ever-helpful outside pocket) and B) you like the lady-ness of a handbag but your hands aren't always free (hello, top handles and removable shoulder strap). This bag is a workhorse."

2. The Transport Tote

"While I love my Medium Transport Tote, I also own the original, roomier version. This bag can hold everything, and it ages like George Clooney thanks to its soft but durable pebbled leather. It can be whatever you need it to be—dressy, casual, timelessly cool, etc."


(Image credit: @madewell)

3. Washed Leather Motorcycle Jacket 

"If you have been waiting for the right time to pull the trigger on buying a leather jacket, this is it. This style has been a Madewell staple for what feels like decades because it's made of buttery-soft leather, has just the right amount of hardware, achieves that ideal just-south-of-cropped length, and is tailored but not stiff. It looks like you've had it forever and will last at least that long. It looks classic with jeans and really punches up a dress."

4. The Boardwalk Post Slide Sandals

"These are the effortless, cute, go-with-anything sandals everyone deserves. They are truly functional, with an almost-invisible toe strap that will keep these puppies from flying off your feet while you're strolling/speed-walking/boppin' around. Wear them with jeans and a T-shirt to achieve the ultimate easygoing, low-maintenance look. Allow them to temper a sweet little frock when sneakers aren't cutting it. They are sturdy, inexpensive, and will last you through many summers to come."


(Image credit: @madewell)

5. 10-Inch High-Rise Skinny Jeans

"These were and always will be the go-to recommendation to customers because that sky-high rise is endlessly supportive and comfy, the denim is soft and just stretchy enough, and any butt (quote me!) looks good with these on. You can get these with a raw hem, an exposed button fly, in a variety of inseams, fits, and washes, and you will always be happy you put them on."

6. Slim Demi-Boot Jeans

"The Slim Demi-Boot is a fresh take on the ever-popular Cali Demi-Boot. I love the Slim because you get a little more length, a little less flair, and still get all the high-waisted, quirky, vintage-y goodness of the original. Put these on with your favorite boots! Tuck in a chunky sweater! Enjoy!"

7. The Ex-Boyfriend Shirt

"Madewell is as much known for its shirting as it is for its denim, and the Ex-Boyfriend flannel button-down is IT if you love versatile pieces. It's slightly oversize, which makes it the perfect layering piece—scrunched under overalls, thrown over a turtleneck or sweatshirt, tucked in or knotted at the waist. It's a shirt you'll reach for again and again. (And don't miss the poplin version!)"

8. Fest Aviator Sunglasses

"These sunglasses are the perfect shape on almost every face. They're lightweight, and they're inexpensive. They will make you look cool(er). Do not delay."

9. Harper Mules

"This mule is further evidence of Madewell's dedication to timeless, go-with-everything designs. They are the perfect height, comfortable enough to wear all day, can be easily dressed up or down, and never slide off your feet mid-stride. The sleekness of the leather and subtly pointed toe are perfectly balanced out by the natural-wood stacked heel. They are an everyday, all-day shoe, and everyone deserves that kind of stability in their life."

10. Frances Skimmer Mules

"If you love the Harper Mule but want a style with less height and more personality, let me introduce you to Frances. What she lacks in height she makes up for in attitude thanks to a pointed toe that means business and a hint of bougie house slipper. These shoes will effortlessly take you from the office to after-work drinks to weekend getaways thanks to their sassy-meets-casual style and their impossibly comfortable soles. You just might never take them off."


(Image credit: @madewell)

11. Courier Shirt

"Yet another Madewell item that continually flies off the racks! This slightly oversize, short-sleeve button-up always looks good, in every situation on everybody it graces. I'm a sucker for a boxy blouse, and this one is made of weighty cotton, so it hangs beautifully on everyone."

Speaking of basics, women over 50 know not to forget these wardrobe staples at H&M, Topshop, and Zara

This story was published at an earlier date and has since been updated.


Anna is an editor on the fashion team at Who What Wear and has been at the company for over five years, having begun her career in the Los Angeles office before relocating to New York, where she's currently based. Having always been passionate about pursuing a career in fashion, she built up her experience interning at the likes of Michael Kors, A.L.C., and College Fashionista before joining the team as a post-graduate assistant editor. Anna has penned a number of interviews with Who What Wear's cover stars over the years, including A-listers Megan Fox, Issa Rae, and Emma Chamberlain. She's earned a reputation for scouting new and emerging brands from across the globe and championing them to our audience of millions. While fashion is her main wheelhouse, Anna led the launch of WWW Travels last year, a new lifestyle vertical that highlights all things travel through a fashion-person lens. She is passionate about shopping vintage, whether it be at a favorite local outpost or an on-the-road discovery, and has amassed a wardrobe full of unique finds. When she's not writing, you can find her shooting street imagery on her film camera, attempting to learn a fourth or fifth language, or planning her next trip across the globe.