The ugly-pretty trend is here to stay, so if you’ve been holding out on giving it a whirl, why not make 2016 the year that you finally embrace it wholeheartedly — or at least see what it’s all about? The word “ugly” alone is probably enough to throw your sartorial sensibilities for a loop, but with pieces like slide-on sandals and body-swallowing sweaters taking the runways and the streets by storm (not to mention being SUPER comfy), there’s definitely something behind this unexpected trend. So break out of your sartorial comfort zone with these 13 ugly pieces that will actually upgrade your look in the new year.
Ugly Trend to Try in 2016: ’90s Beanies
Why They’re “Ugly”: Beanies are quickly becoming the must-have topper for 2016, ousting fedoras and floppy hats from their highly coveted seat of sartorial power. While the soft caps are easy and effortless when they’re loosely knit and pom pom-topped, in their more condensed form, they bring back memories of Hot Topic, Mallrats‘ Jay and Avril Lavigne — eek. Not to mention, the beanie isn’t always one to sit pretty, creating an awkward hourglass shape on top of your head.
Why You’ll Love Them: Their ’90s-inspired flair pairs perfectly with the slew of throwback denim in circulation right now, as well as any and all athleisure ensembles. They also make bad hair days a thing of the past, with a soft, flexible structure that keeps hat hair at bay. To sum it up — just do it.
Try: BDG Cuffed Rib-Knit Beanie ($19) for a slightly sporty take on the versatile topper that will pull together any weekend getup.
Ugly Trend to Try in 2016: Anything but Skinny Jeans
Why They’re “Ugly”: Mom jeans, cropped flares, you name it — the rise of the anti-skinny jean is totally unexpected. Let’s be honest — a few years ago, we would have looked right at these new silhouettes and scratched our heads and beelined our eyeballs to their traditionally unappealing features — baggy fits and and capri-like cuts that we shunned even way back when.
Why You’ll Love Them: Denim is a wardrobe staple, but sticking to only one silhouette can be a little bit boring. Donning a different style can instantly perk up even the most basic of closet basics, plus most of the new cuts and fits are comfortable to boot — so what are you waiting for?
Try: A pair of cropped flares, like this Mother Denim Insider Crop Step Fray Jeans ($228) set, teamed with pointed-toe ankle boots and a chunky knit sweater — the perfect balance of comfort and style.
Ugly Trend to Try in 2016: Double Denim
Why It’s “Ugly”: Whether you call it Double denim, DD or the Canadian tuxedo, the all-jean-everything look has never exactly been the pinnacle of fashion. Maybe because it’s never really been executed properly (exhibit A: Britney Spears and Justin Timberlake circa 2001), or maybe it’s just the jeans-and-a-denim-shirt formula that needs to be reworked. Either way, it’s a whole lot of look.
Why You’ll Love It: Denim didn’t become a closet stronghold for nothing. It’s easy, effortless and casually cool, so really, why wouldn’t you want to double up? The key to pulling it off successfully is to work with different hues, weights and textures to break things up and create visual intrigue.
Try: Do things differently and ditch the jeans for a Madewell Denim Jumper Dress ($128) paired with a chambray top and black denim jacket.
Ugly Trend to Try in 2016: Statement Socks That Show
Why They’re “Ugly”: Birks and socks. Open-toe shoes and socks. Mules and socks. Are you shivering yet? The out-in-the-open look has traditionally been viewed as frumpy, and for that reason has never really received much fanfare. That and it embodies the whole granny chic thing, yet another trend that takes some guts to get on board with.
Why You’ll Love Them: Funky socks instantly inject life and energy into a pair of standard steppers, plus they’ll keep feet that much cozier when the temps take a plunge. Sometimes wrong just feels so right.
Try: Hansel from Basel Toby Anklets ($14) if you’re looking to really make those heels stand out, or slip on a pair of glittery metallic socks if you’re up for something a bit more on the subtle side.
Ugly Trend to Try in 2015: Culottes
Why They’re “Ugly”: An awkward fusion of pants, shorts and wide-leg trousers, culottes actually have a long sartorial history. Back in the day they offered women the versatility of pants, while maintaining a skirt-like and thus lady-like appearance. While that’s all well and good, with both pants and skirts at our disposal nowadays, why don this highly confused pair?
Why You’ll Love Them: Flirting the line between masculine and feminine, they’re the ultimate compromise for the girl that loves experimenting with modern, androgynous looks.
Try: Zara Faux Leather Culottes ($40) with a simple tee, longline blazer and chunky heeled ankle boots for a nine-to-five getup that feels runway ready.
Ugly Trend to Try in 2016: Glove Shoes
Why They’re “Ugly”: Glove shoes give off a bit of a cartoon-like quality that you’d expect from a whimsical Walt Disney flick. But because they’re frill-free, these simple shoes have the whole minimalist chic thing down pat. That means they pack plenty of versatility too.
Why You’ll Love Them: You’ll get major mileage out of these unfussy kicks with their laid-back neutrality, providing the perfect finishing touch for many an off-duty ensemble.
Try: Charles & Keith Slip-on Flats ($39) are a wear-everywhere option that will bring a cool, masculine edge to a go-to jumpsuit and LBD, while bringing classic denim and sweaters into the 21st century.
Ugly Trend to Try in 2016: Sweater Pants
Why They’re “Ugly”: This über comfy look takes sweatpants to a whole new level. The fashionably undone aesthetic has been gaining momentum over the last few seasons, finally reaching new heights with the emergence of knitted bottoms.
Why You’ll Love Them: While sweats have a tendency to look sloppy, sweater pants and skirts have an ever-so-slightly polished appeal. In other words, they’re the latest way to make PJs and sweats outside the house work, meaning waking up and facing the day is that much easier.
Try: Mango Ribbed Trousers ($60) with an elegant blouse and menswear-inspired loafers for a dressed-down-dressed-up outfit that’s fit for your nine to five.
Ugly Trend to Try in 2016: Menswear-Inspired Platform Shoes
Why They’re “Ugly”: Platforms are notorious for infusing everything from heels to sandals with a grunge-glam edge, but when boyish silhouettes and finishings are thrown into the mix, it creates a look that’s a lot to handle.
Why You’ll Love Them: They might be a little clunky, but these borrowed-from-the-boys kicks deliver that much-sought-after height without the ache of classic heels — hello, new fave commuting shoe. Plus, they balance out oversized silhouettes like a boss and add wow-factor to office-ready basics.
Try: Clarks Originals Priddy Silver Leather Walla Sneakers ($171) feel sleek and chic, but will keep feet happy as you hop around town. And they’re polished enough to rock while you’re on the clock. A major #winwin.
Ugly Trend to Try in 2016: Turtleneck Sweaters
Why They’re “Ugly”: Turtlenecks might be back in a big way, but not everyone is convinced by their neck-engulfing tendencies. The wintry tops can feel restricting and a little bit stuffy.
Why You’ll Love Them: With the onset of oversized styles, turtlenecks are more comfortable than ever and will keep you cozy on even the coldest of days.
Try: Tuck a Loft Fireside Sweater ($60) into a sophisticated pencil skirt and pair with minimalist hoops and lace-up pumps for a laid-back office ensemble. Off-duty, get real casual with relaxed joggers and slip-on sneakers.
Ugly Trend to Try in 2016: Paperbag Waistlines
Why They’re “Ugly”: Sartorially speaking, paper bags are just about as far from haute as you can get. So the recent obsession with skirts and pants with bunchy, scrunched waistlines is kind of a mystery. But as it turns out, everyone can make a paper bag look good.
Why You’ll Love It: It’s not often that runway trends translate to real life, but the cinched-in waists of paper bag trousers and skirts look like a million bucks on everyone. Staying on-trend couldn’t be easier.
Try: Topshop Paperbag Midi Skirt ($85) teamed with a sleeveless turtleneck top and mules for a mid-century-meets-modern-day vibe.
Ugly Trend to Try in 2016: Palazzo Pants
Why They’re “Ugly”: Remember raver pants from back in the ’90s? They didn’t work then — how could they possibly work now? Elegant tailoring, sophisticated add-ons and of-the-moment prints have taken the debatable silhouette into fashion-forward territory.
Why You’ll Love Them: The relaxed silhouette is airy and light, adding ethereal movement to any getup. The billowy trousers are also ideal for winter. They can easily be layered over leggings or flannel tights for lots of warmth without the bulk.
Try: For a leisurely work week look, pair Erika Cavallini Semicouture Crosshatch Palazzo Pants ($338) with an oversized turtleneck or, for a bit more polish, rock with a sleek blazer and a bow-neck blouse.
Trend to Try in 2016: Non-Functional Pockets
Why They’re “Ugly”: Pockets are often-overlooked embellishments that make life *so* much easier, from providing a secret place to stash your phone to an indispensable hold-all for everything from chapstick to spare change and travel tickets. A world without pockets would be a sad one to say the least. But big, bulky and oversized interpretations of the utility-packed add-on toe the line between “ugh” and “ooh” in so many ways.
Why You’ll Love Them: Unlike cargo pockets, the 2015-2016 alternative is way more chic. Think of them more as a totally new way to jazz up everything from tailored tops to billowing bottoms. They’re perfect for the girl that loves duds that combine both utility and style.
Try: ASOS White Cotton Sweater With Clear Pocket ($117) for a majorly minimalist chic look. Style with slim-cut pants and futuristic heels.
Ugly Trend to Try in 2016: Overalls
Why They’re “Ugly”: Overalls are a hard sell for anyone over the age of nine. Their childlike quality no doubt delivers a serious dose of nostalgia, but the one-piece wonder also stands in direct opposition to that sophisticated persona you’ve been trying to create.
Why You’ll Love Them: They combine the best features of comfortable jeans and a glam jumpsuit for a statement-making hero piece that’ll ensure you won’t go unnoticed. To bring the onesie into adult-appropriate territory, pair with polished and on-trend separates.
Try: Forever21 Distressed Overalls ($33) with classic Dr. Martens and a turtleneck tee for a ’90s-inspired look. Or, for a flirty, fun feel, go monochromatic and pair with a ruffled top and sleek stiletto sandals.
Will you finally embrace the ugly-pretty trend in 2016? Share your favorite styling tips with us on Twitter!