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.