Relaxed Fit Shoes

Relaxed fit shoes are designed for everyday comfort, making it easy to enjoy every step—whether you're heading out for a walk, running errands, or spending time with friends and family. With timeless style and dependable quality, these shoes offer lasting value you can count on season after season. Find your new favorite pair and experience how relaxed fit shoes can help you stay comfortable and ready for whatever the day brings.

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Men's Kennebec Slip-On Shoes

A versatile slip-on with premium full-grain leather, True Comfort footbed, and VertiGrip outsole for reliable traction.

Pros: High quality Nice looking Perfect fit Attractive style Comfortable
Men's Handsewn Moccasins, Camp Moc

A classic full-grain leather moccasin with a rubber sole and moisture-wicking insole for ultimate comfort.

Pros: High quality Warmth Durable Classic style Comfortable fit
Men's Casco Bay Boat Mocs

A light brown leather boat moc with a siped-rubber outsole for superior grip on wet surfaces.

Pros: High quality Durable Stylish Comfortable Good fit
Men's Stonington Shoes, Moc-Toes

A rugged dark cocoa leather shoe with sneaker-like comfort, water-resistant protection, and a molded rubber outsole.

Pros: Well-made construction Lightweight Versatile design Water-resistant leather Comfortable fit
Men's Stonington Oxford Shoes, Plain Toe

A rugged deepest brown leather shoe with sneaker-like comfort, water-resistant Nor'easter leather, and molded rubber outsole.

Pros: Attractive color Versatile design Comfortable out of the box True to size Non-slip soles
Men's Bean's Comfort Fitness Walking Shoes

A weatherproof, cushioned walking shoe with a breathable polyester mesh upper and durable VertiGrip rubber outsole.

Pros: Fit Quality Comfort Durability Arch support
Women's Eco Bay Leather Slip-Ons

A pair of slip-on sneakers in light coffee or slate blue, made from soft pebbled nubuck leather.

Pros: Cute look Stylish Versatile Good sole support Chic
Men's Kennebec Oxford Shoes

A versatile asphalt leather oxford with athletic comfort, anti-odor footbed, and reliable VertiGrip traction.

Pros: Great fit Versatile style Dressy look Comfortable Nice color
Men's Mountainville Shoes, Leather Lace-Up
Price was from: $109 now: $74.99

A pair of light coffee leather lace-up shoes with a supportive footbed and excellent traction.

Pros: Attractive design Comfortable fit
Men's Kennebec Boat Shoes, 3-Eye
Price was from: $119 now: $99.99

A dark mushroom leather boat shoe with athletic sneaker comfort, wet grip, and a 360 lacing system.
Men's Higgins Beach 4-Eye Slip-Ons, Print
Price was from: $79.95 now: $54.99

A lightweight, breathable canvas slip-on with a deep olive camo print and durable EVA outsole.
Men's Downeast Slip-Ons, Wool

A cozy, thermoregulating wool slip-on with a durable rubber outsole and cushioned EVA footbed.
Men's Higgins Beach 4-Eye Lace-Up Shoes, Canvas
Price was from: $79.95 now: $54.99

A lightweight tan canvas lace-up shoe with EVA outsole and Comfort Ride midsole for all-day comfort.
Men's Higgins Beach 4-Eye Slip-Ons, Fabric
Price was from: $69.95 now: $59.99

A lightweight, breathable slip-on shoe with a flexible polyester upper and durable EVA outsole for summer comfort.

Relaxed Fit Shoes

When it comes to shoes, comfort is always in style—especially during the long, sun-filled days of August, when you want to spend every possible moment outside. Relaxed fit shoes are designed with roomy silhouettes and thoughtful details that make every step feel effortless, whether you’re strolling through the farmer’s market, heading to a backyard barbecue, or setting out on a spontaneous weekend getaway. Their versatile nature means they’re just as at home on a casual walk around the neighborhood as they are while running errands or exploring a new trail with the family. For anyone who appreciates footwear that doesn’t pinch or restrict, relaxed fit shoes deliver all-day ease without sacrificing durability or lasting value. Thanks to quality materials and supportive construction, they hold up beautifully to daily wear, season after season, and transition seamlessly from one activity to the next.

Relaxed fit shoes are a smart choice for anyone who prizes comfort, but they’re especially appreciated by those who spend long hours on their feet, have wider feet, or simply want a little extra wiggle room. They make thoughtful gifts for parents, grandparents, teachers, or anyone whose days are filled with activity and movement. Picture slipping into a pair after a day at the lake, or lacing them up before heading out for an evening walk with the dog—these shoes are the ones you’ll reach for again and again. Their timeless style pairs well with everything from jeans and shorts to khakis and casual dresses, making them a reliable staple for any wardrobe. And because they’re easy to slip on and off, they’re a favorite for travel, quick outings, or those moments when you need to dash out the door in a hurry. If you’re looking to round out your relaxed wardrobe, you might also enjoy our collection of Relaxed Fit Golf Shirts, designed to keep you just as comfortable and at ease on the green or around town.

As summer winds down and routines shift toward back-to-school schedules or fall adventures, relaxed fit shoes continue to shine. Their easygoing design adapts to changing activities and unpredictable weather, offering reliable traction and support whether you’re navigating a dewy morning lawn or heading out for a late-summer picnic. For families, these shoes are a dependable option that works for kids and adults alike, taking the guesswork out of getting ready for the day. With their classic look and enduring comfort, relaxed fit shoes are more than just footwear—they’re an invitation to slow down, savor the season, and embrace every opportunity to get outside and make memories.

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Relaxed Fit Shoes