December is the perfect month to combine cozy warmth with streetwear flair, creating looks that are both stylish and functional. Streetwear in winter allows you to play with textures, layers, and bold statement pieces while staying comfortable in chilly weather. From oversized hoodies to puffer jackets, chunky boots, and layered accessories, December streetwear offers endless inspiration to express your personality and creativity.
Whether you’re running errands, meeting friends, or exploring the city, these 18 streetwear looks merge casual comfort with urban chic. Get ready to layer, mix textures, and explore fun winter colors with outfits that keep you warm and effortlessly cool.
1. Oversized Hoodie with Joggers
An oversized hoodie paired with matching joggers is streetwear comfort at its peak. The loose fit keeps you cozy and allows freedom of movement, while the monochrome or muted tones make it effortlessly stylish.
Perfect for casual days, coffee runs, or relaxed outings, this combination balances comfort with street-smart aesthetics. Adding accessories or sneakers can elevate the look from basic to trendy.
How to Style It: Pair with chunky sneakers, a crossbody bag, and a beanie for a chic street vibe.
Why You Must Try It: It’s cozy, easy to wear, and perfect for making casual winter days stylish without effort.
2. Puffer Jacket with Skinny Jeans
A cropped or oversized puffer jacket layered over skinny jeans is the ultimate December streetwear look. The puffer adds warmth and a bold silhouette, while the fitted jeans create balance and structure.
This outfit works for city walks, shopping trips, or casual meet-ups. Layering underneath a hoodie or sweater enhances warmth and dimension.
How to Style It: Add combat boots, a beanie, and a backpack for an urban-chic finish.
Why You Must Try It: It’s practical, stylish, and perfect for creating a cozy yet edgy streetwear look.
3. Oversized Flannel Shirt over a Graphic Tee
Layering an oversized flannel shirt over a graphic tee creates casual, effortless street style with a winter twist. The flannel adds warmth, texture, and a hint of grunge, while the tee brings personality and color.
This layered outfit is perfect for hanging out with friends, running errands, or exploring the city on colder days.
How to Style It: Pair with ripped jeans, high-top sneakers, and a knit beanie.
Why You Must Try It: It’s versatile, cozy, and perfect for expressing your personality while staying streetwear-ready in December.
4. Faux Leather Jacket with Hoodie
A faux leather jacket layered over a hoodie is edgy, warm, and perfect for December streetwear. The jacket adds structure and style, while the hoodie keeps you cozy and casual.
This combo balances tough and soft elements, creating a modern urban vibe suitable for nights out or city adventures.
How to Style It: Pair with joggers or ripped jeans and ankle boots or sneakers.
Why You Must Try It: It’s bold, stylish, and ideal for layering textures in cold-weather streetwear.
5. Bomber Jacket over a Sweatshirt
A bomber jacket paired with a cozy sweatshirt is a classic streetwear layering choice. The cropped structure of the bomber creates a stylish contrast with the loose sweatshirt, producing a balanced winter outfit. It’s perfect for casual outings, weekend adventures, or even coffee dates.
How to Style It: Pair with slim joggers, sneakers, and a bucket hat for added street style flair.
Why You Must Try It: It’s practical, trendy, and brings effortless cool to your December outfits.
6. Denim Jacket with Oversized Sweater
Layering an oversized sweater under a denim jacket combines warmth and urban appeal. The soft sweater adds volume and texture, while the denim jacket provides structure and a laid-back vibe. This layered look works for daytime outings, shopping, or casual winter activities.
How to Style It: Pair with leggings or skinny jeans, combat boots, and a crossbody bag.
Why You Must Try It: It’s casual, cozy, and perfect for creating dimension in your winter streetwear wardrobe.
7. Hoodie Dress with Over-the-Knee Boots
A hoodie dress paired with over-the-knee boots is a playful yet chic streetwear look for December. The oversized hoodie dress offers comfort, while the tall boots add a stylish edge and balance the silhouette. This outfit is ideal for casual city strolls or weekend hangouts.
How to Style It: Add a mini backpack and hoop earrings for a polished street style vibe.
Why You Must Try It: It’s comfy, trendy, and perfect for blending casual comfort with winter-ready style.
8. Track Pants with Puffer Vest
Track pants paired with a puffer vest create a sporty streetwear look that’s perfect for winter layering. The vest adds warmth without bulk, while the track pants maintain comfort and mobility. It’s a practical outfit for running errands, weekend travel, or casual outdoor activities.
How to Style It: Pair with chunky sneakers, a beanie, and a casual tote bag.
Why You Must Try It: It’s easy, functional, and perfect for combining athleisure with winter-ready layering.
9. Statement Coat with Graphic Tee and Jeans
Pairing a statement coat with a graphic tee and jeans creates a winter streetwear look that’s bold yet cozy. The coat adds color, texture, or pattern, while the graphic tee keeps the outfit casual and expressive. This layered style is perfect for weekend outings or city adventures.
How to Style It: Pair with high-top sneakers and a crossbody bag to complete the urban chic look.
Why You Must Try It: It’s expressive, comfortable, and perfect for making a stylish statement in December.
10. Oversized Hoodie with Biker Shorts and Tights
An oversized hoodie paired with biker shorts and tights is a playful streetwear look for milder December days. The hoodie offers warmth and a relaxed silhouette, while the layered tights make it seasonally appropriate. It’s an ideal combination for casual hangouts, coffee runs, or errands.
How to Style It: Pair with chunky sneakers and a fanny pack worn crossbody for an urban touch.
Why You Must Try It: It’s trendy, youthful, and perfect for mixing sporty and cozy streetwear layers.
11. Parka with Cargo Pants
Layering a parka over cargo pants delivers a practical yet stylish streetwear outfit. The parka provides insulation against cold, while the cargo pants bring structure, texture, and utilitarian style. This look is perfect for outdoor activities or urban exploration in December.
How to Style It: Add chunky boots, a beanie, and a crossbody bag for an effortlessly cool urban vibe.
Why You Must Try It: It’s functional, edgy, and ideal for embracing winter streetwear utility fashion.
12. Knit Beanie and Scarf with Oversized Hoodie
Pairing a knit beanie and scarf with an oversized hoodie creates a cozy, winter-ready streetwear look. The accessories add warmth, texture, and visual interest, elevating the casual hoodie into a stylish layered outfit suitable for city strolls or outdoor social events.
How to Style It: Pair with skinny jeans, ankle boots, and a casual backpack.
Why You Must Try It: It’s simple, chic, and perfect for layering winter accessories into your streetwear outfits.
13. Cropped Sweater with High-Waisted Jeans
A cropped sweater layered over a fitted long-sleeve or tee paired with high-waisted jeans creates a chic streetwear look with flattering proportions.
The cropped layer adds dimension, while the high-waisted jeans elongate the silhouette. Perfect for casual December outings or city strolls, it’s a mix of comfort and style.
How to Style It: Add chunky sneakers, a belt bag, and hoop earrings.
Why You Must Try It: It’s flattering, trendy, and perfect for playful, casual streetwear layering.
14. Hoodie Under a Faux-Fur Coat
A hoodie under a faux-fur coat is a cozy and trendy winter streetwear combination. The hoodie adds casual comfort, while the faux-fur coat brings texture, luxury, and warmth.
This layered look is perfect for evenings out, casual gatherings, or cold weather adventures where style meets functionality.
How to Style It: Pair with skinny jeans, knee-high boots, and a crossbody bag.
Why You Must Try It: It’s luxurious, warm, and streetwear-ready—perfect for chic December layering.
15. Oversized Tee with Leggings and Longline Coat
Layering an oversized tee over leggings with a longline coat creates a relaxed and effortless streetwear look. The coat adds structure, while the tee and leggings keep the outfit casual and comfortable. Perfect for casual city outings, brunches, or weekend errands.
How to Style It: Add chunky sneakers, a knit beanie, and a belt bag for streetwear appeal.
Why You Must Try It: It’s easy, comfy, and perfect for casual yet stylish winter layering.
16. Hoodie with Pleated Skirt
Pairing a hoodie with a pleated skirt blends sporty and feminine elements, creating a playful streetwear look for December. The hoodie adds comfort and warmth, while the skirt brings movement and structure. This outfit is perfect for casual meet-ups or festive city walks.
How to Style It: Pair with ankle boots, patterned tights, and a mini backpack.
Why You Must Try It: It’s unique, comfortable, and perfect for combining edgy and girly streetwear layers.
17. Puffer Coat with Sweater Dress
Layer a puffer coat over a sweater dress for a streetwear look that’s cozy, stylish, and winter-ready. The dress adds a soft, comfortable layer, while the puffer creates warmth and urban appeal. This outfit works for casual outings, coffee runs, or weekend adventures.
How to Style It: Add sneakers or ankle boots, and a beanie to complete the street-ready winter look.
Why You Must Try It: It’s practical, chic, and perfect for combining warmth with streetwear style.
18. Statement Hoodie with Joggers
A statement hoodie paired with matching joggers is a bold, urban streetwear look perfect for December. The matching set creates a cohesive vibe, while unique prints or bold logos make it trendy and attention-grabbing. Layering under a long coat or puffer adds warmth and versatility.
How to Style It: Pair with chunky sneakers, a crossbody bag, and a beanie for maximum streetwear impact.
Why You Must Try It: It’s comfy, expressive, and perfect for making a fun, trendy statement in winter.
Conclusion
December streetwear combines warmth, comfort, and style effortlessly. These 18 outfit ideas show that layering, textures, and bold pieces can make even casual looks chic and city-ready. From oversized hoodies to puffer jackets, statement pieces, and playful accessories, streetwear allows you to experiment with your personal style while staying cozy.
Whether exploring the city, meeting friends, or running errands, these looks offer practical warmth, easy styling, and maximum street-style impact. Embrace layering, mix textures, and let your December wardrobe reflect both creativity and comfort while keeping you stylish and ready for every urban adventure.