Trans-Seasonal Footwear
Loafers and Boat Shoes for the win
February in New York is when things feel real Wintery. It’s when ballet flats don’t quite make the cut, much to my dismay. What is the ideal footwear for those chilly days when you crave something more refined than a sneaker but don’t want to opt for boots? I’m a longtime fan of loafers—they’re the ultimate transitional shoe, versatile enough for year-round wear. I love them both with and without cozy socks.
Another favorite of mine is the casual boat shoe, which serves as a perfect trans-seasonal option. Whether paired with a slouchy cashmere sock for a cozy winter look or worn in spring with a more relaxed vibe, it strikes the right balance.
Last week, I found myself walking around on a cold, rainy day. I was headed to a lunch uptown, but didn’t want to reach for my boots or sneakers. Instead, I chose my Bass Weejun loafers, paired with a ribbed sock. They were the perfect balance—not too precious to wear outdoors in the rain, and the reason why the Weejun remains a staple in my wardrobe. I rely on having a range of loafers in my collection, from more polished styles with leather outsoles to chunkier versions with lug soles, which are ideal for a more laid-back, comfortable look.
After lunch, I wandered around Bergdorf Goodman’s shoe floor, where I spotted the exact pair I was missing from my collection—a chic, ruched, menswear-inspired loafer. Clean, minimal, and with a strong toe shape, smooth calf leather upper, and a sturdy leather outsole made it the perfect match for a silky sock and ideal for city walks. I could easily see myself wearing them for the remainder of the season and beyond. I had been eyeing the ruched soft loafer from The Row (I even found a great dupe here), but ultimately I preferred a broader toe shape, making this new pair the perfect addition to my wardrobe.
Flattered makes a great soft and ruched loafer that I’ve been seeing and it also comes in suede. I also love the very affordable soft penny loafer from Massimo Dutti - there are actually so many great shoes in their newest collection.
I have a soft spot for a more slipper-like loafer, and have the Canal loafer from The Row. It serves as a great option when I am sockless — it’s buttery and soft, the ultimate in comfort, as it has a nice rubber outsole. But I find that it’s not a good for a long day on your feet. Here are some of my favorite sleeker loafers that range from a very clean topline, to a classic take on a penny loafer. I love how unconstructed and soft the Jamie Haller loafer is — there’s no break-in needed on her shoes, which is worth paying for.
Suede is another favorite —the texture is rich and velvety, and it offers immediate comfort thanks to its supple, forgiving nature. I’m especially drawn to the deep chocolate brown and earthy tones, which have a timeless, classic appeal.
Moving onto the boat shoe. Another classic silhouette — with lots of heritage. I love that it feels fresh again in the mix. Lots of options in the market at the moment, ranging from Miu Miu’s distressed leather pair, to Bally’s take with the slimmer toe box. I also found a really good bootie from Massimo Dutti - unconstructed and smooshy, a good casual but elevated take on the style.
And then to the classic deck shoes from the original brands like Sperry and LL Bean. I have been wearing this incredible pair by Caron Callahan and I love the fun laces - there are easy and fun ways to put your personal spin on these with patterned or contrast colored shoe laces…
I got to attend
’s EV Salon event — Sperry provided us with boat shoes and a wonderful beading bar to customize the laces. DIY and natural wine at Sauced was a perfect start to Fashion Week.
And here’s a sneak peak of one of Sperry’s newest collection. Obsessed with the woven upper and the leather outsole…
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I bought the suede Massimo Dutti’s!
I have the suede MiuMiu boat shoes! I love them.