Four brave local designers take on the challenge of turning the aptly named holiday staple into an object of desire—or at least a more palatable one. All of their own creations are proudly made in Chicago, and the sweaters carefully picked by Kokorokoko vintage shop (kokorokokovintage.com).
Anastasia Chatzka (anastasiachatzka.com)
“I styled my look with a classic high-waisted mini skirt and a bold plaid crop top to offset the boxiness of the Christmas sweater. My advice for making a “fugly” Xmas sweater looking cool is looking at the silhouette and patterns. If your shirt is tight go with a full circle skirt, and if it’s a huge sweater go with a skinny jean or tight skirt. If it’s a cardigan like the one I am wearing, pick a bold print to wear under it. This will help break up the focus on the sweater. Then your outfit becomes a Christmas look with the sweater being an accent!
Skirt ($85) and crop top ($45): Anastasia Chatzka
Tights: Tabbisocks ($20, sold at Anastasia Chatzka)
Scrunchy socks: Urban Outfitters
Lee Allison (leeallison.com)
“So this crazy (but kind of lovable) Christmas cardigan has six festive Scottish Terriers on the front. My first thought was that the best accessory of all would be an actual live Scottie, dressed up in his own Christmas sweater! But that was hard to pull off on short notice, so I found this leather dog and tiny sweater at Petco. Needless to say, I call this look ‘doggy style.’ I then put a solid red Lee Allison bow tie on ‘Boris,’ while I’m wearing one of our green Nordic Christmas bows, as well as a Lee Allison boutonniere stick-pin, also in green. To make the look complete, I put the sweater on backwards, so basically I’m a mullet haircut—all business in front, party in the back.”
Bow ties: Lee Allison ($78 each)
Boutonniere: Lee Allison ($29)
Anna Hovet (annahovet.com)
“This sweater is very… um…. eccentric, yet the oversized cozy style of it actually goes well with our Sport Luxe apparel brand! To neutralize the look, I paired it with our super-comfy black and cream bamboo joggers. The neck accessory is our 8-in-1 Dakota Funnel Collar that also transforms into a hat or headband. To give the outfit a high-fashion look while maintaining the streetwear vibe, I chose a funky pair of boots by Chelsea Jones, an awesome local shoe designer. The red beret from Goorin Brothers is my staple fall accessory that adds a sophisticated vibe to any fall ensemble.”
Collar: HOVET Convertible Dakota Collar ($35)
Pants: Anna Hovet Chelsea Joggers ($89)
Hat: Goorin Brothers
Shoes: Chelsea Jones
Jim Snediker of Stock MFG Co. (stockmfg.co)
“For this look, we decided to go with the Ugly Sweater layered under a casual suit. We wanted to add a touch of style and sophistication to the traditional Ugly Christmas Sweater, while still keeping the fun and goofiness of this new holiday tradition. We layered the sweater under our Sportsman’s Jacket and over our Fisherman’s Shirt, with a pair of our Caramel Six Point pants and Waxed Earth Iron Rangers on the bottom.”
—Isa Giallorenzo/Photos provided by the designers, who modeled the looks themselves
Journalist Isa Giallorenzo was born in São Paulo, Brazil and has elected Chicago as her beloved home since 2009. She runs the street-style blog Chicago Looks and wants to see this town become one of the fashion capitals of the world.