In today’s dynamic fashion landscape, the grandpa shoes trend has gained significant attention from designers, celebrities, and street-style enthusiasts.
Imagine slipping into comfortable, practical loafers or oxfords that evoke the nostalgic charm of your grandfather’s wardrobe. Think rich brown leathers, suede finishes, and grippy soles for all-day wear. But don’t let the name fool you; these aren’t dusty relics from the past.
In 2026, grandpa shoes have been reimagined as a symbol of quiet luxury, blending functionality with modern edge to create footwear that’s as versatile as it is stylish.
What started as a subtle nod to grandpacore aesthetics, borrowing from elders’ closets for effortless, menswear-inspired ease, has exploded into a mainstream phenomenon. From the runways of Fall 2025 to the streets of New York and London, these shoes prove that comfort does not have to compromise sophistication.
Photo: Getty Images Brands like Miu Miu, The Row, and New Balance are leading the charge, offering silhouettes that pair seamlessly with everything from tailored trousers to sheer skirts.
As Marissa Galante Frank, fashion director at Bloomingdale’s, aptly puts it, “Heels still have their place, but there’s a clear appetite for silhouettes that feel practical without sacrificing style.”
This trend’s rise is not just about aesthetics; it marks a cultural shift toward sustainable, timeless pieces in a fast-fashion era. Influences range from 19th-century Oxford University styles to contemporary grandpa outfit revivals, offering a bridge between generations.
Whether you are a fashion novice curious about updating your wardrobe or a trendsetter looking to stay ahead, this guide dives into the grandpa shoes trend.
We will explore its origins, why it is dominating 2026, celebrity-approved looks, styling tips, top picks, and more. By the end, you will be ready to step into this comfortable revolution and make it your own. Let’s lace up and get started.
What Are Grandpa Shoes? Defining the Trend
The grandpa shoes trend centres on footwear that emphasises comfort, durability, and classic style. It includes loafers, oxfords, derbies, boat shoes, and select slip-on moccasins or trekking sandals, rather than flashy sneakers or high heels.
Key features include practical soles for daily use, low or no heels, and materials such as leather, suede, or shearling. Typical designs use understated brown tones and subtle hardware, prioritising reliability over trendiness.
Unlike the chunky “dad shoes” popular in previous years, the grandpa style features a more refined, vintage-inspired silhouette.
Photo: 305pics/Getty Images Oxfords feature a closed-lacing system for a structured appearance, while derbies have an open-lace design for a more casual look. Boat shoes add a preppy element with grippy soles and comfortable linings, making them suitable for transitional weather.
As Vogue notes, the definition of a grandpa shoe is subjective and often depends on styling choices, such as pairing them with white socks and turned-up trousers.
The trend also includes sneakers, with brands like New Balance introducing models like the Allerdale that combine orthopaedic comfort with a sleek design.
Clogs such as Merrell’s Jungle Moc also align with the trend, featuring cushioned soles that emphasise functionality. Their versatility appeals to a wide audience, supporting a gender-fluid approach to style.
The Historical Roots of Grandpa Shoes
The grandpa shoes trend has deep historical roots, blending utility with cultural significance. Oxfords, for example, originated in the early 1800s at Oxford University as a comfortable alternative to bulky boots. These low-cut shoes soon became associated with Ivy League style and later gained popularity in Hollywood and beyond.
Loafers also have a notable history, evolving from Norwegian fishermen’s slip-ons in the 1930s and popularised by G.H. Bass as the Weejun style. Derbies and boat shoes originate from menswear traditions and are often linked to preppy revivals.
In British culture, references to shows like Last of the Summer Wine add a whimsical element, inspiring designers such as Jonathan Anderson.
Photo: Getty Images In the 21st century, these styles have experienced several revivals. The 2020s saw the rise of “granny shoes” such as Scholl sandals, followed by grandpa versions during the quiet luxury trend.
By 2024-2025, collaborations such as Mephisto with Procell transformed orthopaedic sneakers into sought-after items, marking a shift from dad to grandpa aesthetics. In 2026, brands continue to update classic styles with features like pre-aged soles and mesh overlays for enhanced breathability.
Why the Grandpa Shoes Trend Is Booming in 2026
In 2026, the grandpa shoes trend thrives due to a combination of practicality, nostalgia, and innovation. Post-pandemic fashion emphasises comfort and style, and these shoes meet both needs. Major runways from Fall 2025 to Spring 2026 featured them, often styled with relaxed menswear for a quietly confident look.
Social media platforms such as TikTok and Instagram have amplified the trend, showcasing a variety of “grandpa steppers” outfits. The style aligns with broader movements like “eclectic grandpa,” which combines striped knits, oversized glasses, and tailored pieces. While some anticipate a shift toward other trends, strong sales for brands like Mephisto and Merrell indicate their continued popularity.
Economic factors also contribute, as consumers seek timeless, durable footwear during uncertain times. The trend’s gender-neutral appeal further broadens its relevance across diverse wardrobes.
Celebrity Endorsements and Runway Highlights
Celebrity endorsements have further popularised the trend. Harry Styles wore The Row loafers with white socks and grey trousers, reflecting classic style.
Kendall Jenner and Alexa Chung offer subtle interpretations, while Aubrey Plaza pairs brown Reformation loafers with skirt suits for a preppy-feminine look. Gigi Hadid styles Miu Miu versions with knit pants and polos.
Photo: Neil Mockford On the runway, Miu Miu’s Fall 2025 collection featured worn-in loafers with ribbed socks, Loewe incorporated high-shine hardware, and Bottega Veneta’s Resort 2025 included glossed booties with chinos and ties. JW Anderson’s collections highlight patchwork slip-ons, demonstrating the trend’s innovative direction.
How to Style Grandpa Shoes: Tips and Outfit Ideas
Thoughtful styling is essential to maintain a modern appearance. For example, pair loafers with lace slips or voluminous skirts, as suggested by stylist Elizabeth Cardinal Tamkin. For boat shoes, consider cashmere socks and a leather jacket with relaxed jeans.
Outfit ideas
- Preppy Chic: Oxfords with pleated minis, ribbed socks, and oversized blazers.
- Casual Cool: Derbies with straight-leg denim, button-downs, and frilly socks.
- Layered Luxe: Boat shoes with high-waisted chinos, striped shirts, and woven jackets.
- Modern Prep: Loafers with tights and skirt suits for work-to-weekend transitions.
Experiment with colours such as chocolate brown for fall and use suede for added texture. Accessories like wired earphones or tote bags can further enhance the grandpa aesthetic.
Best Grandpa Shoes Brands and Models to Buy in 2026
Consider these recommended options:
The Future of Grandpa Shoes Beyond 2026
Looking ahead, the trend is expected to evolve with technological updates such as breathable mesh in Merrell’s Jungle Trek Moc.
While some styles, like boat shoes, may decline in popularity, hybrids such as wedge trainers indicate ongoing innovation. Sustainability will continue to drive demand for durable, eco-friendly materials.
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