Ordering shoes online means you can't try them on before you buy — but a proper foot measurement gets you almost as close. It takes about five minutes, a few household items, and gives you the two numbers that matter most: length and width. Here's how to do it right. 

Fall is hard on shoes. One day it's sunny and 70, the next you're walking through puddles on the way to your 8am class. Temperature swings, surprise rain, and the general chaos of back-to-school and back-to-office schedules mean your favorite pair is working overtime this season — and that's exactly when leather and suede need the most attention. 

Between early classes, late study sessions, and everything in between, your shoe rotation has to work as hard as you do. The secret to never overthinking your footwear again? A capsule wardrobe — a small, versatile lineup of shoes that takes you from dorm room to lecture hall (and everywhere after) without missing a beat. Here are the four Sperry styles that belong in every student's closet.

Spring 2026 is shaping up to be a season of effortless polish. Think romantic details, timeless prep, and soft neutral tones that work with everything. The best part? These shoe trends aren’t just stylish—they’re wearable, versatile, and made to last beyond one season. Here’s what we’re stepping into for Spring 2026.

Two of our classic styles, reimagined through the lens of Matt McCormick. Expect Western inspiration, classic stitching, rugged detailing, and more.

From bringing a twist to officewear to making the effortless transition from the sea to the streets, the Aritzia x Sperry Authentic Original Boat Shoes do it all. Here are our favorite ways we've seen them styled IRL.

Good shoes make an outfit not by stealing the show, but by giving you a platform to elevate your look. We asked stylist Anda Gentile, known for her fresh and original take on classic preppy style, to showcase the many ways people can use Sperry boat shoes to build different looks. Using the iconic Authentic Original Boat Shoe and the modern, fashion-forward Wells Boat Shoe, Anda put together four looks that’ll have you standing out at work, on downtown nights out, casual weekends and for midday lunches. See All Authentic Original™Shop Authentic Original™ Boat Shoe Weekend Warrior The always-stylish boat shoe is a comfortable way to bring a touch of refinement to your more laid-back weekend looks. The 360° Lacing System™ and Wave-Siping™ outsoles make them versatile and practical, while the classic moccasin-stitched upper only gets better the more you wear it. "As the mom of a skateboarder, I often spend hours at skateparks in different cities. My weekend style is all about street-style layers, ready for anything—whether it’s sitting for hours or jumping in on the fun. I love pairing warm coats with shorts or layers so I’m sure to be extra prepared- but also looking cute and maintaining a New York style that I’ve worn basically since I was little and playing in these NY streets." Downtown Nights The iconic boat shoe can be dressed up with ease, bringing a touch of effortless elegance to your evening looks, whether it’s date night or you’re meeting up with friends for drinks. Luxe leather and premium finishings ensure the Authentic Original never looks out of place – just like you. "I often feel like I have to switch between different personas to match the fashion environment I'm working in on any given day. At heart, though, I'm such a tomboy—except when I go out at night. Then, I enjoy playing the part of the girl who pairs dressy skirts with something a bit more edgy, like sheer socks, a touch of leather, and fun jewelry. And just like that, I’m ready to go!" Photographer: David 'Shadi' Perez @shadinyc Lunch Dates On the other side of the coin, the boat shoe is a great way to bring a polished touch to your more casual looks. Anda leans into the silhouette’s preppiness by pairing it with corduroy pants and Oxford shirt, to bring an elevated, but effortless look to midday lunches and casual get-togethers. "Whether I’m traveling for work or meeting a friend for lunch, my go-to style has a New York 70’s vibe. Growing up in a city with such rich fashion culture, it naturally becomes part of you. From collegiate prep looks to corduroy suits with layers, or vintage bell-bottom jeans with an old tee, I always incorporate these elements into casual events. Here, I’ve layered a brown corduroy suit with a pop of color, added a vintage taxi-style hat, a fun striped sock, and finished the look with my favorite Sperrys." Photographer: Hector Perez @hectornyc

When it comes to the Sperry Authentic Original™ Boat Shoe and other Sperry boat shoes, they should feel like they were made for you. With over 80 years of craftsmanship, we’ve perfected the true-to-you fit. Here are some tips for how Sperry boat shoes should fit and finding your size.   Sperry leather boat shoes0197640_000 Wear your Sperry leather boat shoes often to break them in. The hand-sewn leather moccasin construction will mold to your foot over time. Plus, our Authentic Original Boat Shoe has 360° lacing, so you can tighten up when you’re on the go and loosen up for a laid-back weekend. Size your shoes up, or down?Leather will stretch over time. If you’re buying Sperry leather shoes, consider buying a half size down from your regular size. If the shoes are made of synthetic materials, get your normal size. Synthetic materials won’t stretch; they’re constructed to hold their shape (i.e., size). Keep in mind, breaking in your new leather boat shoes will only affect the width (not the length). Need extra width? Or are your feet narrow Shop our shoes in Extended Widths—wide, extra wide, and slim. How do you wear your boat shoes? Socks or no socks?socks The sock vs. no-sock debate continues. No-show socks are the perfect answer to the debate. Wearing no-show socks with your Sperry boat shoes helps with odor protection and added comfort. If you’re going to rock a sock, plan for a little extra room. When to shop for new shoes?When shopping, consider trying on Sperry boat shoes toward the end of the day. During the day, gravity will bring fluid to your feet causing a bit of swelling. The footbed will compress over time, providing a little extra wiggle room. If you’re still not sure you have the right size? The Sperry customer service team is always here to help answer your sizing and other questions. Want to find out more about Sperry shoes?Check out other “how-to” blogs about Sperry shoes. And there’s more! Here’s the complete collection of informative and inspiring Sperry blogs. Ready to shop?Find the complete Sperry collection for men, women, and kids.

Robb Report calls Sperry’s iconic CVO sneaker “the purest simplest classic.” Here’s why You probably know that Paul Sperry invented the first boat shoe after slipping off his boat in 1934. After pulling himself out of the cold Long Island Sound, Sperry set out to design a non-slip shoe that would keep its grip even on wet decks. Inspired by the grooved paws of his dog Prince, who never slipped on board, Sperry invented the very first non-slip boat shoe. What you may not realize is that this shoe was not what we call the Top-Sider Authentic Original Boat Shoe today, but, in fact was the CVO sneaker. HISTORY-OF-SPERRY-1941 The CVO- (or Circular Vamp Oxford) is iconic in its simplicity – quick-drying canvas upper, grooved rubber sole, simple design. With a design that riffs off the classic oxford shoes, the CVO became the official shoe of the US Navy, and a favorite of Sperry’s yacht club members. The shoe has been spotted on everyone from JFK to Mr. Rogers, and style leaders around the world for decades, and is available on Sperry.com in a range of colors, with Birch being the ultimate classic hue– still made using the same manufacturing techniques that have been used for over 8 decades. Still a wardrobe staple, Robb Report says of the CVO “It is to sneakers, one could argue, what Levi’s 501s are to denim: the purest, simplest classic.” Read more about this must-have shoe here.