Shoesday #1: My 20 Favorite Loafers To Buy Right Now

The first edition of a new, every Tuesday newsletter dedicated to shoes.

This is the first edition of a weekly, footwear-centric column I’m calling “Shoesday.”

Whether I’ve been penning a trend piece on the rise of the Paraboot Michael, creating a column dedicated to the latest hyped up sneaker, or generally just being a sicko who continues to cop despite owning more footwear than I could possibly wear in a lifetime, shoes are without a doubt the clothing category I’ve thought the most about throughout my style career. If I had to unpack why that is, I’d say that for one, shoes never get boring—after all, they can take on an infinite amount of forms while still meeting the fundamental criteria of being, well, “shoes.” I also love how footwear is so vital to one’s style despite covering a relatively small portion of one’s overall surface area. On one hand, the right shoes can elevate an otherwise plain look to “Big Fit” status, while on the other, the wrong shoes can upend an otherwise well-intentioned get-up faster than you can say “Vibram.”

I say all of this to explain why I’m starting a new weekly column today that’s entirely dedicated to footwear. I’m calling it “Shoesday” because it’ll drop every Tuesday and I can’t resist an opportunity for a good pun.

Though this column won’t always be in list format (I’m assuming I’ll often highlight a single shoe I’m into, for example) for the first edition of Shoesday, I’m bringing you a round-up of what is one of the most essential footwear categories to have in your arsenal: loafers. As I wrote for Robb Report in 2023, we’re currently living in the golden age of the style, which is to say, there have never been more brands offering up stylish forms of these iconic slip-ons than right now. But with so many purveyors vying for attention in the loafer economy, I’ve taken it upon myself to swoop in and narrow down the market to what I think are the top 20 to know about this season. The pairs you’ll find below are wide ranging and will ensure you’re suited for any occasion, whether the day calls for hand-crafted shell cordovan loafers to stand-up to your best, uh, suit, or some breathable basket-woven numbers you can sport on the beach. Enjoy!!!

This newsletter is ENTIRELY funded by subscriptions. I don’t use affiliate links, and all of these products are things I’ve endorsed and/or included because I actually like them, though in some cases I did not pay for them. Point is, your subscriptions are both extremely cool and very much appreciated. Thank you!

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And now, for today’s post…

My Favorite Loafers For Spring-Summer 2025

Madewell x GH Bass Lennox Loafers, $195

A great entry-level tassel loafer from one of my favorite clothing brands, Madewell, and the company that made Penny Loafers possible, GH Bass. If they’re anything like my other loafers these two teamed up on, then expect them to be supple and comfortable right out of the box, too.

Morjas Ivy Loafer, $400

Swedish label Morjas has skyrocketed to popularity over the last few years for a simple reason: They make some of the best-looking dress shoes that, despite being made like a pair of shoes that could fetch 4 figures, will typically only set you back around 4 bills. Exhibit A: The lovely suede loafers above that are a pared-down, timeless version of a classic.