How to Wear 9 Polarizing Fashion Trends, According to Stylists

"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

Birkenstock Kyoto Sandals ($140)

Comme Si Merino Wool Socks ($30)

Eftychia Beige Rib Deep Polo Cardigan ($389, originally $720)

Eftychia Brown Basic Centre Seam Trousers ($281, originally $720)

The Row Slouchy Banana Small Textured-Leather Shoulder Bag ($1,890)

Birkenstock Arizona EVA Sandal ($45)

COS Relaxed Cotton-Linen Pants ($89)

Kotn Essential Crew ($25)

Krewe Earhart Optical Glasses ($315)

Birkenstock Arizona Soft Footbed Sandals ($135)

Agolde Vintage Cotton-Blend Corduroy Flared Pants ($160)

Nessy Khem Sacha Smokey Brown Aviator ($195, originally $325)

"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

Dr. Martens 1461 Bex Oxford ($130)

Mother Baby Steps MF Socks ($24)

Free People Posey Plaid Pants ($60, originally $78)

Cotton Citizen Brooklyn Oversized Zip Hoodie ($265)

"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

Adidas Originals Ozweego Suede and Neoprene-Trimmed Mesh Sneakers ($110)

Réalisation Par The Isabelli Dress ($180)

Gap Vintage Soft Raglan Sweatshirt ($40)

HBX Classic Logo Cap ($55)

Prada Re-Edition 2005 Nylon and Saffiano Leather Mini-Bag ($770)

"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

Eric Javits Kaya Leopard-Print Hat ($250)

Zara Top With Ruching ($36)

ASOS Design Tapered Boyfriend Jeans ($60)

Labucq Boomer Sandal ($350)

Ganni Printed Cotton Poplin Hat ($59, originally $85)

Totême Espera Rib Tank ($105)

Weekday Rail Mid Straight Jeans ($70)

New Balance 624 Sneakers ($75)

"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

Crocs Neria Pro II Clog ($55)

Veda Belize Top ($238)

Loulou Studio Bermuda Pleated Wool-Twill Shorts ($230)

Ronny Kobo Denita Cardigan ($328)

Jannesa Leoné Kai Hat ($267)

Nike Three-Pack White Everyday Essential Crew Socks ($15)

Vehla Lotta Sunglasses ($170)

Crocs Classc Clog ($40)

Sol Angeles Essential Coastal Pullover ($114)

Sol Angeles Essential Coastal Jogger ($114)

Crocs x Chinatown Market Jibbitz Shoe Charm ($6)

"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

Patagonia Worn Wear Airshed Pullover ($63)

Girlfriend Collective Smoke High-Rise Bike Short ($48)

Chaco Z/1 Classic Wide Width Sandals ($95, originally $105)

Rawganique Organic Hemp Terry Socks ($16)

Ashley Rowe Tan Bucket Hat ($95)

The North Face Reconstructed Side Bag ($186)

Stamp It Earrings ($68)

Wonther Life Link Necklace ($157)

"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

Aje Psychedelia Pleat Wide Leg Trouser ($325)

Orseund Iris Cha Cha Top ($185)

Musier Paris Drew Top ($76)

Asics Gel-Kayano 5 360 Sneakers ($150)

Free People Pop Over Pant Set ($70, originally $168)

Emme Parsons Bari Sandals ($395)

Ramy Brook Scalloped Fallon Top ($172, originally $245)

Recc Paris Amour Necklace ($72)

"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

Nike Everyday Plus Cushion Crew ($22)

Levi's 701 Crop Taper Jeans ($236, originally $278)

Ganni Jewel Loafers ($425)

High Heel Jungle Leave Me Alone Cotton Socks ($29)

Reebok Classic Leather Sneakers ($75)

Varley Vine Pullover ($158)

Paige High Rise Cindy Jeans ($225)

"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

KkCo Utility Vest ($465)

Tibi Eco Poplin Cape Dress ($695)

Avenue Erika Bucket Hat ($48, originally $69)

Crocs Classic Clog ($45)

Vince Runyon Bottle Bag ($265)