They were once fashion’s biggest punchline—but now, they’re making a serious style comeback. Yes, we’re talking about those “ugly” shoes. Love them or hate them, they’ve found their way back onto the feet of trendsetters everywhere—and surprisingly, they’re looking better than ever.
The secret? It’s all in the styling. Ahead, we’re breaking down 8 outfits that completely flipped our opinion and proved these polarizing pairs can actually be chic.
1. Preppy Layers Make ‘Ugly’ Shoes Look Chic
Chunky brown moccasin-style sneakers might not scream fashion at first glance, but this layered look gives them a major style upgrade. Paired with gray slouchy socks and preppy light blue jorts, they add a grounded, collegiate edge.
A powder blue shirt peeks from beneath a cozy gray cardigan and plaid vest combo, creating texture and interest up top. Oversized glasses and a plush backpack with playful charms complete the quirky, street-smart aesthetic. It’s the kind of outfit that proves so-called “ugly” shoes can actually be the coolest part of the look.
2. Boat Shoes Get a Cool-Girl Makeover
Once considered a preppy relic, tan boat shoes look effortlessly fresh in this laid-back, modern outfit. Paired with crisp white knee-length jorts and a tucked-in vintage graphic tee, the look feels retro yet totally on-trend.
The white belt adds a hint of structure, while round sunglasses and tousled hair bring that off-duty cool factor. Minimal accessories and neutral tones keep the outfit grounded and wearable. Proof that even the most “uncool” shoes can look fashion-forward when styled with a wink of nonchalance.
3. Country Club Cool Gets a Modern Edge
Classic brown loafers step out of their preppy comfort zone in this sophisticated yet casual ensemble. Styled with cuffed high-waisted trousers and a one-shoulder black top, the look blends elegance with weekend ease. The oversized brown handbag and luxe watch add polish, while a baseball cap and visor sunglasses lend sporty contrast.
Every accessory is intentional—creating a head-to-toe monochrome moment that feels elevated, not overdone. It’s a perfect example of how “dad shoes” can look unmistakably chic when the rest of the outfit plays smart.
4. Boat Shoes, But Make It Street Style
Traditional brown boat shoes are reimagined here with a cool-girl, city-ready twist. Paired with tailored pinstripe shorts and a crisp white tee, the look stays grounded yet relaxed. The oversized denim shirt acts as a laid-back jacket, adding structure without trying too hard.
A baseball cap and a mint green handbag bring sporty charm and color play, while the crossbody strap detail adds utility flair. It’s the kind of outfit that proves boat shoes aren’t just for the docks—they’re for the sidewalks too.
5. Preppy with a Twist
A perfect blend of slouchy streetwear and polished prep, this look makes a case for the revival of classic moccasin-style loafers. Styled with visible socks, cuffed light-wash jeans, and an oversized striped polo, the outfit leans effortlessly cool.
A knotted suede jacket at the waist adds an earthy touch, while the Louis Vuitton shoulder bag brings in luxury contrast. It’s an ideal example of how so-called “ugly” shoes can be reimagined as fashion-forward when grounded in balance and intention.
6. The Cool-Girl Loafer Look
Proof that basics never go out of style, this outfit elevates the humble loafer into street-style territory. Distressed jorts and an oversized white tee give off a borrowed-from-the-boys vibe, balanced by gold layered necklaces and a woven leather bag for softness.
The choice of traditional brown loafers grounds the look, making it an ideal mix of relaxed and refined. Add a cold brew and sunglasses, and you’ve got downtown chic with zero effort.
7. Preppy Meets Urban
Who knew boat shoes could look this good off deck? Styled with voluminous cream trousers, a striped rugby tee, and a caramel trench, they channel a collegiate vibe with a modern twist.
The chocolate-brown layering and luxe handbag elevate the look into polished territory, while the shoes ground the whole outfit with an unexpected, cool nonchalance. A brilliant example of how a so-called “ugly” shoe trend can be the final touch to a seriously stylish look.
8. Polished Prep Gets a Refresh
Tan shorts and a crisp striped blouse set a timeless tone, but it’s the boat shoes that pull this look together with undeniable charm. Matching the warm neutrals of her accessories, they enhance the preppy aesthetic without looking dated.
With oversized sunglasses, a straw hat in hand, and a structured weekender bag, the entire outfit feels vacation-ready while proving once again that this “ugly” shoe is anything but. Their nautical roots give the ensemble a relaxed sophistication that works effortlessly from sidewalk to seaside.