Here are 5 ways to style your favorite big flannel without looking homeless: Wear it as a dress. Share using Facebook. Share using Twitter. Tie it around your waist. Share using Facebook. Tuck it into jeans. Share using Facebook. Pair it with shorts and tights. Share using Facebook. Layer it under denim. Share using Facebook. Click to see full answer. Also question is, how do you wear an oversized flannel woman? How To Wear Flannel Without Looking Sloppy Say something and pair a flannel with a statement tee. Tuck it in for a refined silhouette. Make it work-appropriate with a chic cape and booties. Break up a monochrome theme with the plaid pattern. Dress up the button down with your favorite accessories — like a hat! Layer it under a vest for extra warmth. Likewise, how do you wear an oversized plaid shirt? For a grunge-y edge, grab your oversized plaid shirt and wear it with a crop top and your favorite trousers or leggings. Complete the ensemble with a pair of comfy boots or other stylish footwear. These beauties are a trendy and fun way to spend a casual day running errands or shopping. . Thereof, what do you wear with flannels? For a casual look, pair your flannel shirt with a T-shirt, some jeans, and some boots or sneakers. When the weather gets warm, tie your flannel shirt around your waist or roll up the sleeves. For a smart casual style, wear your flannel tucked in with some chinos, a belt, and some suede derby shoes.Are flannels out of style?Flannel will never go out of style because it is that one rare type of clothing that has managed to hold onto some conventionalism (e.g., the classic plaid flannel shirt) while also evolving and venturing into new territories, such as with bold colors and new prints.