Grandpa shoes, with their practical and chunky silhouette, are becoming the new street style favorite in 2026. Rising from grandpa’s wardrobe to the runway, they prove that comfort can be stylish. They offer old-fashioned elegance without sacrificing modern appeal.
## Trend Origins and Runway Ignition
This trend continues the popularity of “grandma sandals,” with Miu Miu, Prada, and Loewe leading the way in re-releasing them, incorporating wool linings and square toes. Kendall Jenner’s street style demonstrates how to pair them with wide-leg pants or mini skirts, instantly balancing ruggedness with sophistication.
Designers are drawing inspiration from 70s walking shoes, emphasizing leather craftsmanship and cushioned soles, replacing chunky dad shoes and echoing a slow-living aesthetic.
## Classic Style Categories
| Shoe Type | Key Elements | 2026 Highlights |
| Oxford Shoes | Closed laces, smooth leather, sleek square toe | Calvin Klein runway, formal with suits |
| Derby Shoes | Open laces, suede variation, casual feel | Celine street style, paired with flared trousers |
| Loafers | Strapless slip-in, wool lining, warm and comfortable | Miu Miu hot item, layered with stockings |
| Boat Shoes | Wool or canvas, casual and rugged | Monse Fall/Winter, nautical style |
| Derby Clogs | Thick sole, retro, leather trim | Jil Sander Spring/Summer, avant-garde transformation |
Choose according to the occasion: Oxfords for the office, boat shoes for the weekend.
## Dressing Wisdom, Avoiding Old-Fashioned Looks
Contrasting with feminine tops: Lace camisoles or bubble skirts create a blend of soft and hard; wide-leg trousers add a touch of sophistication and elongate the leg line. Colorful socks or ankle straps add a playful touch, moving away from a monotonous grandfatherly look.
A formal upgrade to a longer trench coat, or a street style version paired with an oversized sweater, is versatile enough for both autumn/winter and spring/summer.
## The Allure and Investment Value Behind Grandpa Shoes
Grandpa shoes represent a legacy of craftsmanship, durable and sustainable, affordable yet luxurious. They remind fashion of its essence: comfort is key to long-term success.
