These Winter Outfits Made Me Believe in Classics Again—Here's Why

Trends: They come and they go, and they sure are fun while they last. But just like those classic TV shows I keep coming back to, I can't deny my need for a handful of reliable fashion items that hold up season after season. I'm talking about the staples: perfect jeans that somehow work with any shoe style, trans-seasonal jackets that layer over anything, a foolproof black outfit that's never too casual or too dressed up. Don't get me wrong—I'm always here for a micro-trend to keep things spicy, but I'll remain a staunch believer in a wardrobe that stands the test of time.

Kit Keenan, daughter of fashion icon Cynthia Rowley, has been making her mark on the New York City fashion scene with her effortlessly sleek style. The Gen-Z star and I are on the same page when it comes to loving a timeless wardrobe, so it was a treat to chat with her about all things winter fashion. When I asked Keenan how she keeps an ever-evolving wardrobe feeling classic, she told me, "I believe in having style, not just necessarily following trends. That doesn't mean you can't take risks. It just means you should discover your personal style and experiment within that before jumping on every hot new trend." I agree, which is why I always turn to collections like AG for its elevated pieces, and so does Keenan. Keep scrolling to see the three winter looks she's currently turning to (and will be wearing for seasons to come).

For me, the best part of a timeless wardrobe is the seemingly endless variations of outfits I can create with what I own. (It's so easy to tweak timeless pieces to make them more or dressy or casual.) The same goes for Keenan, who told me, "The beauty of classic pieces, like a pair of jeans or a jumpsuit, is that they can be dressed up or down to fit most occasions. I could wake up and wear a pair of AG jeans to a coffee meeting with an oversize denim jacket, switch to a blouse if I am recording for my podcast midday, then throw on a blazer and heels for any nighttime events."

Jumpsuits are the year-round staple that Keenan loves to expertly layer based on her mood, the occasion, and the temperature. The addition of a cloud coat, a heritage-print blazer, or a turtleneck underneath totally changes the vibe and gives this classic one-and-done AG piece a new life for the city's cooler seasons.

When it comes to Keenan's style, the West Village resident told me that she looks to historical style icons for inspiration. So it makes sense that the denim trends that resonate with her nod to the best moments from decades past. This season, that means mid-wash boot-cut jeans with a high waist and a raw hem. "I love the revival of flare pants," Keenan emphasized. I'll admit, it's the pairing with this perfectly oversize jean jacket for me. The key to keeping a denim suit feeling fresh? A bright, white, half-tucked knit and modern accessories by way of that buttery clutch and lug-sole boots. A classic color palette.