How to Wear 9 Polarizing Fashion Trends, According to Stylists

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The term "ugly" is undeniably arbitrary. Yet, the word frequently gets tossed around when describing specific fashion trends like chunky sneakers, bucket hats, oversize trousers, Birkenstock sandals, "mom" and "dad" jeans, Crocs, hefty lug-soles, windbreakers, and utility vets. What one can't dispute? The strong statement every one of these pieces makes, which may or may not be your cup of tea. It's totally cool either way. However, if you have recently been racking your brain for fresh outfit ideas and feel as though your go-to looks have run their course, you might consider implementing one of these popular, albeit slightly controversial, trends into your wardrobe.

When it comes to "ugly" fashion trends, the main idea is finding a balance to avoid a polarizing effect. How does one do that? With expert styling! So we sought out advice from eight fashion stylists who are not only pros at making any accessory or article of clothing look stylish, but they're equally keen on wearing a number of these "ugly" trends themselves.

So if you have been mulling over a pair of Birkenstocks, have found yourself tempted by the bucket hat's big return, don't quite know how to balance a baggy trouser, or still can't wrap your head around the chunky-sneaker movement, keep scrolling to discover stylish outfit ideas that feature "ugly" fashion trends. Be sure to take in all the styling tips so you can rock a Croc, embrace a tube sock, and give technical gear the same gusto you would a new dress or sandal.


The "Ugly" Fashion Trend: Birkenstock Sandals

"My forever favorite 'ugly' item is the Birkenstock, the new suede Kyoto pair. I would pair them with a masculine-fit trouser in a similar tone of brown with a tonal knitted top and merino wool socks." — Beverly Nguyen, Kate Young Studio

"The shoe initially associated with granola hippies has become a chic-girl staple, and they're here to stay. The undoubtedly comfortable sandal has a realness to it, and its wearers seem to exude the sentiment, 'I'm confident enough to wear this shoe.' My favorite Brooklyn cool girls rock a pair all year round. Plus, anything that was popular in the '70s is a friend of mine. My favorite way to style Birkenstocks is with a minimalistic, monochrome look. In the summer, I'd go for black linen drawstring pants with a slightly boxy T-shirt paired with a classic all-black Arizona two-strap Birkenstock. The effortlessly chic pajama-style look is clean and airy and pairs perfectly with the Birkenstock classic." — Katie Graner

"I'm wearing my Birkenstocks constantly during the quarantine. I think the most fashionable way to wear them is in a fun color. Mine are metallic, which is a little bit obnoxious, but go big or go home! It used to be super dorky to wear a necklace attached to your sunglasses so you don't lose them, but now brands like Nessy Khem have made it look so cool. I wear these every time I run an errand to spice up my quarantine fit!" — Britt Theodora


The "Ugly" Fashion Trend: Chunky Lug-Sole Shoes

"I'm a shorty at a staggering 5' flat, so when chunky shoes are an option, I'm in! I splurged on [the] Prada [Monolith lug-sole] shoe, and I have not regretted it one bit. They remind me of middle school, and so I like to kind of keep it '90s when styling them. I typically wear them with trousers or denim, spice them up with a sock, and likely top it off with an oversize hoodie. I don't think you can go wrong with these, though; fashion is all about experimenting, after all." — Neelo Noory


The "Ugly" Fashion Trend: Chunky Sneakers

"The revival of chunky sneakers has been hugely popular thanks to the likes of Balenciaga, and over the past few years, chunky trainers have evolved from an ironic comeback trend to a wardrobe staple. A cute way to style them would be with a short dress, and for more of a Scandi vibe, add a sweater, baguette bag, and a cap to finish the look." — Kirsty Stewart


The "Ugly" Fashion Trend: The Bucket Hat

"I've been embracing 'ugly' fashion since I tried on a pair of Crocs for laughs about a year ago. Cut to 2020, and now I wear them incessantly around the house and sometimes out of the house. So does my husband, and now I think they're sexy, especially when he wears them with shorts that hit midthigh and no socks. All we do for kicks now is go for scenic drives, and my go-to looks involve a combination of 'ugly' items, which I see as 'retirement chic.' One combination involves lime-green mom jeans, lug-sole sandals by Labucq, and a bucket hat. I style them around a puff-sleeve top and cute sunglasses for some modern, feminine touches." — Sissy Sainte-Marie Chacon

"The demand for the bucket hat returned, and we have seen them from the likes of Prada, Burberry, Acne Studios, and Ganni for the past year. For a casual feel, keep the rest of your outfit as minimal as possible and let your bucket hat do all the talking. A white tank top, oversize jeans, and trainers would be perfect." — Kirsty Stewart


The "Ugly" Fashion Trend: Crocs

"I love this Croc style. It's the most comfortable shoe I've ever worn and great for lengthy set days; they're easy to kick on and off in studio, and the traction is great for outdoor shoots, a win-win! I feel like these shoes go with everything I own, especially cute with a tall solid-colored sock, printed top, and shorts. Extreme dad vacation vibes are what I typically go for when wearing Crocs." — Neelo Noory

"'Tis the season for comfort! I have been finding new ways to style my matching sweatsuit outfits, and I've recently joined a liking to Crocs. CROCS?! Yes, Crocs. I love that you can insert different charms to add a personal touch. Just throw them on with white tube socks and your favorite sweatpants and call it a day. I adore the white and mint-green pair." — Jaclyn Fleurant


The "Ugly" Fashion Trend: A Windbreaker

"My favorite use of 'ugly' fashion is in a utilitarian application, for example, in the outdoors. I recommend piling on all the cool nerdy technical gear like Chacos with Rawganique hemp socks, a Patagonia Worn-Wear windbreaker, a Greater Goods upcycled bag, and top it all off with an Ashley Rowe oversize bucket hat. Add some Girlfriend Collective bike shorts and Wonther ethical gold jewelry to make it all feel a bit more personal and modern." — Rachael Wang


The "Ugly" Fashion Trend: Oversize Trousers

"It is important to add balance to oversize trousers, so I tend to always have my clients wear a cropped or tank top. More often than not, people will want to reach for a heel, but I love how a trainer or a boot looks, as long as you create a shape on the top, you can wear whatever shoe feels right for the occasion." — Kirsty Stewart

"No one does oversize trousers better than Pamela Tick, and if she approves, so do I! Oversize trousers are the dad-pant turned cool-girl staple that just makes sense. The whole idea is to be effortlessly chic, cool, and comfortable, and oversize trousers are just that. I'm a tomboy at heart, so anything 'borrowed from the boys' is right up my alley. For me, the trick with oversize trousers is to ensure they're high waisted. This way, we still have a feminine element of an accentuated waist, even when oversize. I love this casual set from Free People" — Katie Graner


The "Ugly" Fashion Trend: Tube Socks

"An 'ugly' item I'm always wearing is my tube socks. I love finding socks that have funny phrases on them because if you are going to wear a tube sock, you might as well make a statement." — Britt Theodora

"Wearing these Nike tube socks, in classic white or black, has become a staple in my wardrobe. They truly are such comfortable treats for your feet! I do prefer these athletic socks to be a contrast to the shoe and outfit, so avoid simply pairing them with sneakers and instead go for a sandal, a heel, or a chunky shoe. It's nice to put a new spin on them." — Neelo Noory


The "Ugly" Fashion Trend: The Utility Vest

"The utility vest is a game changer. I no longer have to carry a purse, only a water bottle sling, because the vest has a pocket for all my things: wallet, phone, pepper spray, plus COVID-19 protections like hand sanitizer, rubber gloves, and extra masks. I guess comfort and function are a given, but as far as styling, I say go 80 percent Grandpa or go home." — Sissy Sainte-Marie Chacon