Key Takeaways
- Unassuming brown loafers and oxfords have emerged as one of the most unexpectedly statement-making trends of fall 2025, as the likes of Miu Miu, Calvin Klein, Aubrey Plaza, and Gigi Hadid offer modern styling inspiration.
- Despite their presence in your grandparents’ closet, these shoes are anything but old-fashioned when you pair them with statement socks, straight-leg denim, and playful details.
Boot season may be in full swing, but another, more unexpected footwear category has been quietly taking over: the grandpa shoe. The loafer trend itself is nothing new—it’s been gaining traction for a few seasons now, thanks to its A-list fans and effortless cool-girl appeal—but grandpa loafers and oxfords tap into a nostalgic, niche subset of the look. There’s no chunky lug sole, platform heel, or bedazzled charm in sight: Instead, these are the classic, unfussy brown leather or suede silhouettes your grandpa probably wore with a fisherman sweater and structured slacks. Now, the shoes have broken out of the retirement community and gained cool-girl appeal, emerging as one of the season’s most unexpectedly chic shoe trends.
From rich chocolate suede to sleek brown leather, grandpa shoes are popping up everywhere as the latest quiet-luxury-coded staple to top off fall ‘fits. Whether styled with crisp denim and oversized blazers or frilly socks and pleated skirts, the look feels equal parts old-school and fresh. Ahead, learn all about the grandpa footwear trend—complete with the best pairs to shop and styling tips.
The History of Grandpa Shoes
Long before they became a cool-girl staple, brown loafers earned their reputation as the ultimate classic shoe. The style traces its roots back to the early 20th century, when Norwegian fishermen inspired the first slip-on designs later redefined by brands like G.H. Bass in the 1930s with the now-iconic Weejun loafers. Oxford shoes—also trending as part of the grandpa movement—originated at their namesake university in the 1800s, building a timeless, formal reputation as they rose to popularity across the UK, Hollywood, and more
Originally worn for their practicality and polish, brown loafers quickly transitioned from utilitarian footwear to Ivy League uniform, and eventually, a symbol of timeless preppy style alongside oxfords (so it makes sense that they’re staging a comeback during this fall’s revitalized prep trend). Brown loafers in particular became synonymous with understated sophistication—they were less formal than black, but still stylish enough for just about any occasion.
Decades later, the same laid-back ease and quiet luxury appeal are ensuring “grandpa” shoes like brown loafers and oxfords remain a trending staple—only now, they’re paired with fashion-forward styling and a wink of irony.
About the Trend
Loafers, oxfords, and similarly formal yet comfortable shoes have always been a timeless staple, but brown iterations are having a major moment after taking off on fall 2025 runways including The Row, Miu Miu, and Prada. Miu Miu showcased worn-in brown leather loafers styled with ribbed socks and skirts, while Loewe’s spring 2026 collection offered a glossier, high-shine version accented with metal hardware for a slightly more polished take on the grandpa-core shoe.
Beyond the runways, brown loafers have been getting just as much traction, with trending suede styles becoming an Instagram-worthy fall essential for fashion types. Celebrities are leaning in, too: Aubrey Plaza recently paired brown Reformation loafers with a skirt suit and tights for a preppy, feminine spin, while Gigi Hadid gave her brown leather Miu Miu loafers a loungewear twist with knit pants and a polo for a look that felt laid-back but elevated.
Getty Images
The renaissance of oxfords has been a bit more gradual, trickling its way into the wardrobes of street style fixtures as well as runways like Victoria Beckham and the new era of Calvin Klein under Veronica Leoni. This footwear category has a more formal reputation than loafers, but it’s similarly gotten a styling makeover to make it approachable and effortlessly cool.
Getty Images
The Cool-Girl Appeal
Part of grandpa shoes’ current relevance is because they effortlessly merge several of the most prominent recent fashion aesthetics. They’re the natural next step in the quiet luxury movement—streamlined, understated, and inherently polished—but with a touch more personality than the minimalist staples of seasons past. They also bridge the gap between summer’s boat shoe revival (see: the instantly sold-out Sperry x Aritzia collab) and fall’s return of modern prep, offering a grounded, versatile alternative with a similar nostalgic charm.
@cocoschiffer / Instagram
Together, these buzzy, sought-after styles have paved the way for the rise of “grandpacore”—an aesthetic defined by its comfortable, menswear-inspired ease. The result? A shoe that’s equal parts borrowed from your grandparents’ closet and a celebrated effortless cool-girl staple.
@_livmadeline / Instagram
How to Style
Despite this trend’s “grandpa” namesake, but this season is all about styling these shoes in ways that are anything but old-fashioned. One of the easiest paths to make them feel fresh is by leaning into the modern preppy aesthetic spotted on the runways. At Miu Miu, brown loafers were paired with ribbed or thick socks—a look that instantly feels intentional when styled with a pleated mini or a tailored midi skirt. Statement socks play up the preppy look while adding their own touch of personality.
Getty Images
Consider taking a page from Plaza’s book and style brown loafers with a pair of tights and a skirt for a collegiate-inspired look. For a more classic approach, try pairing your grandpa shoes with straight-leg denim—whether crisp and structured or loose and lived-in—and finish with a button-down or an oversized blazer for a polished, everyday uniform.
If you’re after something softer, swap in frilly socks or pairs with subtle ruffles and pastel tones to bring a playful edge to the menswear-inspired silhouette. And if you want to elevate the look even further, choose a pair with a slight heel or a croc-embossed finish—subtle upgrades that give the traditional grandpa shoe a modern, luxurious twist.
@claire_most / Instagram
The Best Grandpa Shoes to Shop
The timeless, simple nature of this trend means you can opt for any brown loafers, oxfords, or similar that you like—vintage finds and your grandpa’s still-good pair included. That being said, we’ve rounded up a few standout modern selects that highlight the surprising range of this hyper-specific shoe style.
