Milan Fashion Week is often a spectacle of high fashion and luxury, where iconic brands and emerging designers alike showcase their latest collections.
But in recent years, something unexpected has emerged: the “ugly” comfort shoe trend. Initially dismissed as a fad, these shoes have gradually infiltrated mainstream fashion, and this year's Milan Fashion Week solidified their position as a must-have item. Interestingly, the connection between comfort shoes and Halloween is becoming more evident—these odd, sometimes even peculiar designs are perfect for this spooky, dress-up holiday.
The season’s key takeaway? Comfort shoes aren't just for lazy weekends or casual errands anymore—they are here to make a statement, even on Halloween. Below, we’ll dive into some of the most buzzworthy footwear collaborations from Milan Fashion Week that prove the “ugly” comfort shoe is exactly what you need for both style and comfort this Halloween season.
Fendi x Red Wing Boots: The Ultimate Industrial Desert Boot
Price: £600-£700
Fendi’s collaboration with Red Wing has brought a rugged, industrial twist to desert boots that have been a staple in their menswear collections since the 1950s. These iconic boots were modeled during Fendi's Spring/Summer 2025 show at Milan Fashion Week, signaling a strong endorsement of the comfort shoe trend.
Features:
- Industrial Design: The boots blend Fendi’s luxury aesthetics with Red Wing's heritage craftsmanship.
- Comfort: Made with durable leather and featuring cushioned soles, they are designed to withstand hours of wear, making them perfect for a long Halloween night.
- Style: These boots marry utility with style, ideal for a rugged costume—think post-apocalyptic survivor or industrial worker chic.
- Why These Boots are Perfect for Halloween: The chunky, rugged design makes these boots an ideal complement to Halloween costumes that require durability and a tough look. Plus, they’re practical enough to keep you comfortable all night long, even if your Halloween festivities take you from one haunted house to another.
Check out other available hot promo coupons at FENDI >>>> HERE <<<<
Ecco x Natacha Ramsay-Levi Slip-Ons: Minimalism Meets Comfort
Price: £170
Collaborating with former Chloé creative director Natacha Ramsay-Levi, Ecco has designed slip-on shoes that marry minimalist design with maximum comfort. Presented at Milan Fashion Week, these shoes represent the understated side of the “ugly” comfort shoe trend.
Features:
- Slip-On Design: Easy to wear with a clean, minimalist aesthetic.
- Sustainability: Made with high-quality, eco-friendly materials as part of Ecco’s commitment to sustainability.
- Style: Perfect for pairing with casual costumes, like a laid-back zombie or an effortless vampire look.
- Why These Slip-Ons are Perfect for Halloween: These slip-ons are versatile and subtle, making them a comfortable choice if you’re going for a low-key costume. They're also ideal for people who want to be on their feet for hours without compromising comfort or style.
Check out other available hot promo coupons at ECCO >>>> HERE <<<<
Martine Rose x Clarks Heeled Loafers: Edgy Elegance for Halloween
Price: £250
The Martine Rose and Clarks collaboration has brought a sharp, stylish twist to traditional loafers. These heeled loafers, showcased at Milan Fashion Week, are all about blurring the lines between elegance and edginess.
Features:
- Block Heel: Provides added height without sacrificing comfort, thanks to Clarks’ reputation for supportive soles.
- Design: The loafer design is classic but with a modern, edgy twist typical of Martine Rose’s bold aesthetic.
- Style: These shoes can elevate any costume, especially if you're aiming for a polished yet subversive look—think a modern take on a gothic vampire or an aristocratic zombie.
- Why These Loafers are Perfect for Halloween: The heeled loafers offer a sophisticated yet slightly dark twist, making them perfect for a Halloween costume that demands a balance between formality and eeriness. Plus, they’re comfortable enough for long hours of wear.
Check out other available hot promo coupons at Clarks >>>> HERE <<<<
Ecco x Natacha Ramsay-Levi Heels: Eco-Friendly and Chic
Price: £130
If you’re looking for a stylish yet comfortable heel this Halloween, look no further than the Ecco x Natacha Ramsay-Levi heels. These shoes bring the collaboration’s signature minimalist design into a dressier realm, offering a chic option for anyone who wants to look polished.
Features:
- Sustainable Materials: Like the slip-ons, these heels are crafted using environmentally friendly materials.
- Comfortable Heel: Ecco's commitment to ergonomic design ensures these heels offer support and comfort.
- Style: Perfect for costumes that need a touch of elegance without going overboard—think an ethereal witch or a glam Halloween vampire.
- Why These Heels are Perfect for Halloween: These heels give you the lift you need without sacrificing comfort. Their minimalist design makes them adaptable to various Halloween looks, from understated to glamorous, all while being kind to the planet.
UGG x Collina Strada Tall Boots: Comfort Meets Couture
Price: £280-£350
UGG has teamed up with fashion darling Collina Strada to create a collection that blends UGG's signature comfort with Collina Strada's avant-garde, fashion-forward design. These tall boots were a standout during Milan Fashion Week, perfect for making a bold statement.
Features:
- Tall Boot Design: Classic UGG comfort in a tall, knee-high silhouette.
- Bold Style: Collina Strada’s creative input brings bright colors and patterns, adding a unique flair.
- Warmth and Comfort: These boots are lined with UGG’s signature plush interior, making them perfect for cool Halloween nights.
- Why These Tall Boots Are Perfect for Halloween: These bold, statement-making boots are perfect for anyone looking to incorporate fashion into their Halloween costume. Whether you’re dressing as a futuristic warrior or a high-fashion witch, these boots offer both comfort and style.
Check out other available hot promo coupons at Collina Strada >>>> HERE <<<<
UGG x Collina Strada Boots: The Cozy Choice for Halloween
Price: £250-£300
Another collaboration between UGG and Collina Strada, these knee-high boots offer a more casual take compared to the tall version. With a quirky, colorful design, these boots were a hit at Milan Fashion Week, merging UGG’s famous comfort with Collina Strada’s bold style.
Features:
- Knee-High Design: A shorter, more versatile version of the tall boots.
- Playful Patterns: Featuring fun, eye-catching patterns, perfect for adding a playful touch to your Halloween ensemble.
- Cozy Fit: The soft, plush lining ensures warmth and comfort.
- Why These Boots are Perfect for Halloween: These knee-high boots are perfect for a whimsical costume, like a woodland creature or a fairy, while still providing the warmth and comfort needed for a night out in the chilly autumn air.
Check out other available hot promo coupons at UGG >>>> HERE <<<<
Martine Rose x Clarks Ankle Boots: Classic Meets Cool
Price: £160
The Martine Rose x Clarks ankle boots are another example of how the “ugly” comfort shoe trend is not going anywhere. Presented during Milan Fashion Week, these boots fuse Clarks' heritage with Martine Rose’s bold, avant-garde design aesthetic.
Features:
- Ankle Boot Design: Sleek yet sturdy, offering both style and support.
- Comfortable Fit: Designed with Clarks’ signature comfort technology.
- Style: Perfect for adding an edge to any costume, whether you're going for a more gothic look or something quirky and offbeat.
- Why These Ankle Boots are Perfect for Halloween: These boots are a versatile choice for any costume, adding a sleek but slightly rebellious vibe. Pair them with a gothic costume or even something more lighthearted like a steampunk-inspired outfit.
Birkenstock x Tekla Slides: Luxe Comfort for the Minimalist
Price: £410
Birkenstock has long been known for its focus on comfort, and their collaboration with Tekla takes their classic slides to a luxurious level. These high-end slides were a notable feature at Milan Fashion Week, combining Birkenstock’s ergonomic design with Tekla’s understated elegance.
Features:
- Minimalist Design: Clean lines and neutral tones for a sophisticated look.
- Comfortable Fit: Birkenstock’s ergonomic footbed ensures all-day comfort.
- Style: Ideal for those looking for a minimalist costume—think chic ghost or casual zombie.
- Why These Slides are Perfect for Halloween: If you prefer a more laid-back Halloween look but don’t want to sacrifice style, these slides are the perfect choice. They offer supreme comfort, ensuring you can walk or stand for hours without any discomfort.
Check out other available hot promo coupons at Birkenstock UK >>>> HERE <<<<
JW Anderson x Wellipets Slides: Playful Frogs for a Fun Halloween
Price: £350
JW Anderson's collaboration with Wellipets has brought the fun back into fashion footwear with these frog-emblazoned slides. Seen at Milan Fashion Week, these shoes are quirky, bold, and undeniably comfortable.
Features:
- Frog Design: The slides feature an adorable, eye-catching frog motif.
- Waterproof: Perfect for unpredictable weather, these slides are also practical.
- Style: These whimsical slides are perfect for a quirky costume—think fairy-tale creature or magical being.
- Why These Slides are Perfect for Halloween: These slides are ideal for those who want to have a bit of fun with their costume. The playful frog design will make your outfit stand out, while the comfort of the slides ensures you can enjoy Halloween festivities without any foot pain.
Check out other available hot promo coupons at JW Anderson >>>> HERE <<<<
Final Thoughts
Milan Fashion Week has shown that the “ugly” comfort shoe is not just a passing trend—it’s here to stay. Whether you’re looking for a rugged boot, a quirky slide, or a minimalist heel, there’s a comfort shoe that fits every style and Halloween costume.
The trend of “ugly” comfort shoes is proving that fashion doesn’t have to be painful, especially when celebrating a holiday that’s all about fun and creativity. From Fendi’s industrial desert boots to JW Anderson’s playful Wellipets slides, these shoes will keep you looking stylish while ensuring that comfort is key, no matter how spooky or chic your Halloween costume is.
