6 Chic Winter Outfits From Madewell That’ll Have People Believing You Hired a Secret Stylist

Welcome to Let’s Get a Room, a series where editor Eliza Huber heads to the dressing room to try on pieces from your favorite retailers, buzzy items, and new collections. Think of this column as a detailed guide to the pieces that are actually worth buying and the ones that, unfortunately, looked better online—no returns necessary.

If you live in New York and love Madewell, prepare to be amazed by the brand’s new store, which is located right across Prince Street from Prada on Broadway in SoHo. When I visited the flagship location on the morning after its big opening night, it somehow felt like it had always been there—lived-in and comfortable, with customers already bustling in and out to find outfits and gifts ahead of the holidays. A giant tree with presents wrapped underneath and NYC ornaments met me on one side, and a bevy of soft, tailored, and cool fashion items were hung and folded up on the other. The store was nothing if not a cozy oasis from the incessant rain coming down, especially once I began trying on sweater after sweater from the men’s department downstairs. (IYKYK.)

I always start these try-ons by perusing the entire store, touching everything in sight and letting my brain organize what’s available for me to test out. I’m basically a human version of Cher Horowitz’s closet computer. I passed by suede, studs, and faux leather as well as plenty of soft knitwear, outerwear, and, of course, denim. By my second turn around the space, I knew exactly what outfits I wanted to put together, selecting pieces from both the men’s and women’s departments as well as accessories and shoes. (The accessory wall near the dressing rooms is especially tempting if you have a chance to check it out.) I brought 20 to 25 items with me inside what I believe one of the sales associates called the atelier aka the largest dressing room I could find, falling head over heels for 16 of them. Scroll down to see which ones made my final cut.

ENTER THE DRESSING ROOM:

When it comes to classic jeans-and-tee outfits, you can’t go wrong with Madewell. I’ve been wearing the brand’s denim for years, and honestly, it’s never been better than it is right now. I especially like the classic styles like this pair of the ’90s Straight style, which I grabbed in black. I think people incorrectly associate black jeans with nighttime and going out, but I prefer them during the day. They’re sleek and refined but can easily be worn casually—as seen here with a men’s white tee and a terribly soft red crewneck tied around the shoulders. I chose my normal size in them, but if you want a snug, rigid fit, you could probably get away with going a size down. For some extra fun, I threw on a pair of Madewell’s studded suede ankle boots that, according to the Madewell team, were a huge hit among fashion people at the opening-day event. They’re shockingly comfortable thanks to the flexible leather but are also heavy (in a good way), which proved to me that the hardware was top quality.

SHOP MY LOOK:

Okay fine, this isn’t a whole outfit, but after I tried on the last look, I threw on this cropped peacoat-style jacket and had to tell you all about it. First of all, it’s surprisingly warm—probably because of how structured and high-quality it feels. It’s cool worn open, but I also tried buttoning it up and creating the illusion of a funnel-neck collar, which looked very 2024. Highly recommend.

SHOP MY LOOK:

This cropped leather jacket was one of the first items that caught my eye when I entered the store. I knew immediately that I wanted to try it on, and since it’s shorter than a standard leather jacket, I thought it would pair well with a slouchier pair of jeans. I’ve been loving white denim this fall and winter, so this super-wide-leg pair was a perfect choice. I went with my normal size in these jeans, but I honestly wish I had sized up one size to give the look an even more relaxed vibe. Again, though, it’s completely up to you and your tastes.

To texturize this ensemble further, I grabbed two brown suede pieces, one more luxurious than the next. I started with the brand-new and very viral Madewell x Agmes bag, which also comes in red, black, camel, and navy. I also picked up a pair of G.H. Bass loafers from the men’s section. (Just size down 1.5 sizes to go from women’s to men’s sizes.) The combo was perfect, in my humble opinion.

SHOP MY LOOK:

Though casual attire is what Madewell does best, that doesn’t mean you can’t find something a tad more formal inside its new shop. Case in point: this floor-length slip dress in rich chocolate brown. The slit is super high and sexy, making it a great option for a holiday party if you paired it with tights and heels. I, however, went a more chill route, styling it with the above brown loafers for a tonal ensemble and a cream SoftWool crewneck around my shoulders. (I also tried the sweater around my waist, which was equally chic.) This dress is a dream, and anyone would be lucky to add it to their year-round wardrobe. It doesn’t hurt that it’s $158 and 30% off right now when you use the code OHJOY at checkout. Run.

SHOP MY LOOK:

Given the giant tree in the front of the store and overall festive décor of New York City at the moment, I knew I had to try on this all-red skirt-and-jacket set when I spotted it early on in my shopping process. The fabric is so soft and cozy, but the structure of the jacket and length of the skirt make it very sophisticated as well. I especially love how the jacket looked when I tucked the hem under a little bit to give it a bubble-like shape and rolled up the sleeves. It felt more stylized this way. The skirt can be worn lower, making it appear longer, if you buy your normal size or shorter and more fitted if you size down. I prefer it longer and lower and can imagine getting more use out of it by pairing it with a tucked-in button-down shirt and pumps. Honestly, the skirt was probably my favorite tried-on piece of the day.

SHOP MY LOOK:

If there’s one trend I know will be huge in 2025, it’s suede. The luxurious fabric is already taking over, and the year hasn’t even begun yet. Really, when I think of where to shop it, nowhere comes to mind faster than Madewell. That’s likely because of the brand’s wildly successful suede pieces from its first collaboration with Alexa Chung. Though almost every item from that drop is long gone now, more options just dropped in store at the SoHo flagship—just in time for me to try them on. I specifically chose this cognac-colored blazer-and-skirt set, loving the endless combinations I could create with the two pieces. I styled them together with a baggy tee, but you could easily dress up the combo with a sleeker black top or down by wearing them separately, like the blazer with jeans and boots or the skirt with a tank or pretty white blouse and sneakers. With suede this high-quality, whatever you wear will look chic.

SHOP MY LOOK: