Fashion Girlies Are Obsessed With Boat Shoes, and I’m Here to Tell Ya the Hype Is Real

CUSHIONAIRE Anchor Lightweight Boat Shoes

17 Jul 2026, 16:36 · Cosmopolitan

Back in middle school, everyone wore boat shoes, all the time. I’m talking boat shoes with miniskirts, boat shoes with leggings, and boat shoes paired with mesh lacrosse shorts and mid-calf socks (typically worn in the dead of winter for inexplicable reasons). When the craze died down in high school, I was convinced I’d never wear them again. Cut to nearly 20 years later, and I’m writing a love letter to the pair of boat shoes I’ve been wearing nonstop for the past six months. Funny how life works out, right?

Last fall, Miu Miu’s boat shoe-loafer hybrid was alllll over my For You page. The trend trickled down into a collab between Sperry and Aritzia that I was extremely tempted to buy, but no lie—I wasn’t willing to shell out $100+ for a shoe I deemed “trendy.” I did some digging and found a similar pair for less than half the price. As it turns out, they’ve become a workhorse in my wardrobe.

Instead of a traditional boat shoe with a hard sole, these are more of a cross between a boat shoe, a moccasin, and a loafer. They’re honestly one of the comfiest pairs of shoes in my closet. I often struggle with ballet flats because I have wider feet, but these never once gave me blisters. Anytime a shoe comes with zero break-in period, I’m ready to shout my love for them from the rooftops. They also have a cushioned insole, so I was able to log miles in them with ease, unlike other pairs of flats or loafers that offer little in the way of support.

CUSHIONAIRE Anchor Lightweight Boat Shoes $40Amazon

Because these are slimmer and have a more low-profile vibe than the chunky boat shoes I wore back in the day, styling them was easier than I imagined. Dare I say effortless? All autumn long, I found myself wearing them with slightly baggy jeans and a sweater for a classic look that was just as comfy as it was office-appropriate. Basically, in any scenario when I’d wear sneakers or ballet flats, I swapped them for boat shoes.

Edward Berthelot//Getty Images

Moritz Scholz//Getty Images

Once the weather started to warm, I paired mine with a miniskirt and an oversized oxford for a look that felt very prep-school-inspired. I’ve slipped them on with denim cutoffs, a tank, and a pile of colorful beaded necklaces for easy weekend wear. I could also see them looking cute with tailored shorts and a blazer for the office.

Edward Berthelot//Getty Images

Moritz Scholz//Getty Images

Long story short: These quickly went from being a trending nostalgic style I picked up on a whim to one of the most versatile shoes in my closet. Living in New York City means I don’t love having my toes exposed when commuting on the subway, but I also don’t always want to wear socks when it’s nearly 100 degrees. These have proven to be the perfect answer to that dilemma—although I can’t lie, they look chic AF with slouchy socks, so I might have to attempt that next.

While I have absolutely zero qualms about my beloved pair from Amazon, sizing is limited, so I rounded up a handful of other boat shoes I’m eyeing. I’m particularly obsessed with the nautical charms on this pair from Abercrombie’s Sperry collab, although NGL, these designer-inspired mules seem to be calling my name.

More boat shoes to add to cart right this minute:

Classic Sperry’s

Sperry Authentic Original Boat Shoe

Now 28% Off~~$110~~ $79 at AmazonCharmed version

Abercrombie x Sperry Authentic 2-Eye Boat Shoe

$130 at AbercrombieMule version

Sperry Slim Boat Mule

$120 at ZapposBlue suede shoes

Old Navy Faux-Suede Boat Shoes

Now 65% Off~~$40~~ $14 at Old NavyTrendy woven style

Sam Edelman Bria Boat Shoe

Now 41% Off~~$160~~ $95 at NordstromLow-profile designer style

Madison McGeeShopping Editor

Madison McGee is a shopping editor at Hearst Magazines, primarily reporting on home, tech, fashion, and books across titles like Cosmopolitan, Esquire, House Beautiful, Country Living, ELLE, Town & Country, and more. Prior to joining Hearst, she covered pop culture and trending news at BuzzFeed and worked in book publishing. Madison is a graduate of both the University of Mississippi and New York University, where she received her Master’s in book publishing and magazine media. When she’s not writing gift guides, product reviews, and sales and deals content, she’s probably exploring New York City’s independent bookstores or cheering on the Baltimore Ravens.