Entertainment Fashion & Style 20 Ways to Wear Every Pair of Jeans You Own This Winter Share PINTEREST Email Print Street style in frayed hem jeans. Christian Vierig/Getty images Fashion & Style Jeans Accessories Tops & Sweaters Dresses Skirts Pants Outerwear Lingerie & Swimwear Do It Yourself Shoes Skincare Advice Makeup Hair Fragrance Tattoos and Body Piercings Kids and Teens Bumps & Babies Learn More By Catherine Jacobs Updated May 23, 2019 01 of 21 Stylish Outfit Ideas for All Your Jeans Street style in frayed hem jeans. Christian Vierig/Getty images Colder weather is the time when jeans hoarders can bring out all the pairs in their closet and create cozy, stylish outfits. From skinny jeans to distressed, black denim, cropped jeans, flare jeans, and frayed hem styles, we keep on collecting new styles of jeans — but sometimes it's hard to know exactly what to wear with each pair. Don't stress, though! We've got you covered with this street style guide to fashionable winter outfits you can put together with all the different styles of jeans in your closet. 02 of 21 Black Skinny Jeans Black jeans match well with a plaid pattern jacket. Christian Vierig/Getty Images Style a fashionable outfit that nods to normcore-hipster style, when you layer a plaid lumberjack jacket over skinny black jeans and a black t-shirt. Black leather accessories are key to upgrade this casual look. 03 of 21 Black Skinny Jeans Wear faux fur and jeans this winter. Pablo Cuadra/Getty Images Look cute for cold winter days when you wear a nubby black faux fur coat and matching hat with a basic outfit of skinny black jeans and ankle boots. 04 of 21 Boyfriend Jeans Layer a military inspired jacket over slouchy jeans. Christian Vierig/Getty Images Military jackets are a huge trend this season. Wear one with your favorite pair of relaxed boyfriend jeans and some motorcycle boots. 05 of 21 Boyfriend Jeans Wear ripped jeans on a date. Christian Vierig/Getty Images Here's how to dress up an old pair of boyfriend jeans for a date, or going out with friends. You'll look sexy wearing ripped boyfriend jeans, a wrap-style blouse and a nubby textured coat. Ankle boots that feature a shiny texture, or an exotic animal print, are a great match for this outfit. 06 of 21 Boyfriend Jeans Street style floral jacket and cuffed jeans. Edward Berthelot/Getty Images Don't resign your cuffed boyfriend jeans to casual weekends only. Dress them up for brunch or shopping with friends, by pairing them with a pretty floral print jacket, block heel shoes, and a ladylike chain purse. 07 of 21 Boyfriend Jeans Jeans and high heels for work. Vanni Bassetti/Getty Images Is it okay to wear boyfriend jeans to work? We say an enthusiastic yes, if you stick to a neutral color palette with your other separates, and accessorize like a boss. Here, a crisp white blouse and black sweater jacket look right for work with boyfriend denim, thanks to a snazzy leather bag and high heel pumps. 08 of 21 Cropped Jeans Wear jeans with a chunky sweater. Christian Vierig/Getty Images Want to wear cropped jeans when it's cold outside? Layer up with cozy separates that will keep you warm. Case in point — this cute combination of high-waisted, cropped jeans with a chunky grey turtleneck sweater, denim jacket, and long knit scarf. 09 of 21 Cropped Jeans Wear jeans with a trendy poncho. Vanni Bassetti/Getty Images Sometimes, pulling together a fashionable outfit for colder days is as simple as adding the perfect top layer. Here, a basic outfit of cropped jeans and a t-shirt gets a major upgrade, with a richly colored, fringed poncho. Cinching your waist with a thin belt gives you shape in a bulky sweater, creating a go-anywhere outfit that works for dates, shopping or brunch with friends. 10 of 21 Flare Jeans Flare jeans outfit for work. Kirstin Sinclair/Getty Images Flare jeans are often thought of as hippie, but here's a great example of how you can wear them to look chic and sophisticated. A black blouse, white tie-scarf and designer accessories combine with flares to create an outfit you could wear easily to the office or client meetings. 11 of 21 Flare Jeans Parisian style in flare jeans. Kirstin Sinclair/Getty Images What if Parisian style is your jam? Pull together a French girl look in your flare jeans, by matching them with a flowing white blouse that has special details, such as the leather sleeves pictured here. Add classic French-inspired accessories, such as a quilted purse and menswear-inspired loafers, to nail down this look. 12 of 21 Flare Jeans Work outfit with flare jeans and blazer. Kirstin Sinclair/Getty Images Here's another work-appropriate outfit in flare jeans, that makes you look like a boss. Pair a cheerful-hued jacket with dark wash flare jeans, a pin-striped shirt and classic loafers. Add a skinny belt and a designer (or designer look) bag, to be ready for board meetings, interviews or presentations. 13 of 21 Frayed Hem Jeans Street style in frayed hem jeans. Christian Vierig/Getty images Frayed hem jeans are a major fashion trend that's still going strong. Create a fashionable, layered outfit by pairing yours with a slim knit sweater, textured wool coat, and long flowing scarf in neutral hues. Choose high quality, neutral accessories, too, such as the monochrome color block handbag and ankle boots pictured here. 14 of 21 Frayed Hem Jeans Street style outfit in shaggy faux fur and frayed hem jeans. Edward Berthelot/Getty Images How can you instantly winterize a go-to summer outfit of frayed hem jeans and a white t-shirt? By layering on a shaggy, head-turning faux fur coat for a casual glam look, as seen here. 15 of 21 Frayed Hem Jeans Wear an olive parka with cropped black jeans this winter. Christian Vierig/Getty Images Sometimes, looking fabulous is just about choosing one perfect accessory. Worn with sneakers, this outfit of cropped black frayed hem jeans, a trendy olive bomber jacket and a go-to grey hoodie sweatshirt looks basic for weekends. But worn with red high heels, it's instantly chic for parties and going out. That's fashion magic. 16 of 21 Ripped Jeans Wear a long coat over skinny distressed jeans this winter. Christian Vierig/Getty Images Skinny ripped jeans and a classic winter wool coat go together like milk and cookies. Worn with basic sneakers or high heel pumps, you could easily make this your weekend fashion uniform this winter. 17 of 21 Ripped Jeans Winter outfit in jeans and faux fur. Christian Vieirig/Getty Images We love the look of camel colored separates layered over skinny ripped jeans in winter. This outfit of a faux fur jacket, knit sweater and snug-fitting, patchwork jeans is stylish enough for sightseeing, but also warm enough to keep you comfortable on long winter walks with someone special. 18 of 21 Ripped Jeans Ripped jeans and leather jacket street style. Vanni Bassetti/Getty Images Here's how you can dress up ripped boyfriend jeans for a day of lunch and shopping in the city with friends. Pair high-waist, relaxed jeans with a French-style striped tee, leather motorcycle jacket, basic sneakers and big sunglasses. 19 of 21 Skinny Jeans Wear jeans to work with a tailored blazer. Christian Vierig/Getty Images Skinny jeans are a great choice for wearing to the office on denim-friendly days. Wear jeans easily to work and look appropriate, when you match your skinny jeans with a tailored blazer, classic high heel pumps, and a quality leather bag. 20 of 21 Skinny Jeans Street style in a trendy puffer jacket and jeans. Christian Vierig/Getty Images Want to get dressed in a snap and look stylish for casual days this winter? Simply pull on a must-have puffer jacket — we love one that's fur-lined, as pictured here — with your favorite pair of skinny jeans, with or without distressed details. Add a great bag, ankle boots and sunglasses, and you're ready for anything the weekend might bring. 21 of 21 Skinny Jeans Street style in leather jacket and jeans. Christian Vierig/Getty Images Is your style a little bit rock and roll? Cut a cool figure when you pair lighter wash skinny jeanswith a fur-collared leather jacket, layered over a basic t-shirt. Wear with ankle boots and add in your favorite accessories, such as a skinny scarf, chain purse, or cuff bracelet.