Until recently, weddings – whether they were in the middle of summer or the dead of winter – meant a traditionally formal dress code for men: at the very least a suit with a collared shirt, tie and hard-bottomed dress shoes. In the last few years, however, men’s fashion has shifted in a way that makes more casual outfits appropriate for weddings and other formerly formal occasions. Suits are still still welcome, but so, too, are sport coats with trousers, sharp-looking knit polos and shirts without ties. When it comes to footwear, there are all sorts of new possibilities to consider this wedding season, chief among them being the iconic and timeless boat shoe. Loafers & Oxfords Boat Shoes While a handsome boat shoe might be an obvious choice for a wedding at your local yacht club or a seaside destination wedding, the versatile silhouette lends itself to all sorts of outfits and settings, bringing a cool confidence and effortless elegance that’s sure to turn heads. Whether you’re the best man aiming to be best dressed or someone’s plus-one looking to make a good impression without overstepping, a boat shoe strikes the perfect balance between dressed up and down to earth. When paired with a light suit, the boat shoe adds a casual air to suiting, while still nodding to classic preppy codes. It also opens the door to wearing your suits in a less formal manner, say with a polo or an Oxford cloth shirt, without a tie. Alternatively, leather boat shoes bring a refined touch to more laid back ensembles, whether you’re sporting them with light-colored slacks and a dark sport coat – a staple of coastal menswear – or doing away with the jacket and opting for a long-sleeved shirt or knit. Suit Yourself Gold Cup™ Mako Boat Shoe A boat shoe that marries timeless elegance with modern style and cutting-edge technology, making the Gold Cup Mako a versatile pair that can be paired with a relaxed suit or slacks and a polo, depending on the dress code. These boat shoes are expertly crafted from premium leather and nubuck for a refined look and offer a remarkably cushioned and comfortable wear, so you can make the most of the party. Shop Now   Classic Captain’s Oxford If a lace-up is in order, but you still want to tap into effortless coastal cool, consider the Classic Captain’s Oxford, which brings together two preppy icons to create a proper option infused with a preppy touch. Pair these with suits both light or dark and a striped tie for a classic nautical look that won’t seem out of place when you swap the yacht club for the country club. Shop Now   Gold Cup™ Authentic Original™ Handcrafted in Maine Tri-Tone Boat Shoe If you’re the guy everybody looks to to be the life of the party, these handmade-in-Maine tricolor boat shoes are for you. An undeniable conversation starter, these Authentic Originals™ have a story to tell: handcrafted in Maine by skilled craftspeople, a testament to tradition and an ode to an icon of coastal preppy style. With their premium craftsmanship and fun pops of color, these will help elevate your more casual looks to make you the best dressed man – even if you’re not the best man. Shop Now Shoe Care Best Foot Forward Keep your shoes in pristine condition for the big day with a range of essential products designed to clean, protect and hydrate. Shop All Shoe Care The Gold Cup™ Luxury Collection Where superior craftsmanship meets unmatched comfort and style. Elevate your footwear with this pinnacle of luxury. Shop Men's Gold Cup™  

There’s nothing better than a broken-in pair of Sperry leather boat shoes, including the Authentic Original™ boat shoe. The best broken-in boat shoes feel like a second skin. They fit so well that you don’t even realize they’re on your feet. But how do you break in your boat shoes so that they feel amazing?   Wear leather Classic leather is easier to break in than textiles or synthetic leather. Most of Sperry leather shoes are unlined. Because there isn’t another layer that needs to take shape, your leather boat shoes will mold to the shape of your feet quickly. To get that comfortable, broken-in fit, you’ll want to wear your new leather boat shoes a lot when they’re new when the leather is most pliable. Conversely, wearing your new boat shoes less often may impact how fast and how well they mold to your feet. Also, since leather tends to dry out over time, you’ll want to protect leather boat shoes from drying, cracking, and scuffing by treating them with Sperry Leather Cleaner & Conditioner that adds moisture to the leather and keeps your shoes in top-notch shape. Wear the right size To get the right fit, you need to get the right size. Your feet should be comfortable in new shoes. They should be roomy enough for your toes to wiggle and snug enough that they won’t fall off. Too-tight or too-loose shoes can’t be broken in for a good fit—no matter how often or how much you wear your boat shoes. Wear socks? Or not? Whether you wear socks with your boat shoes will also determine how they mold to your feet. Socks will make the shoes feel tighter because they add an extra layer to your feet and may stretch the leather. If you break in your boat shoes wearing socks, then wear the shoes barefoot, they might feel loose.   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.