6 TRENDY STREET STYLE WINTER OUTFITS FOR MEN

Step out in style wearing the season’s latest trends, as spotted on the streets. Whether you’re looking to build your winter wardrobe or are seeking sartorial inspiration to counter the elements, take notes from these men of all ages who show you how to layer up and accessorize your everyday wear.

Related: 7 stylish winter coats for men

From monochrome minimalism to colour-blocking, the streetwear fashion aesthetic for 2023 combines the expected with the unexpected. It’s about picking out wardrobe essentials and pairing them with bold statement accessories or playing with sharp, exaggerated silhouettes. One of the biggest menswear trends in 2023 is tailoring, and we’re seeing it reinterpreted for the street as well in an athleisure-inspired way (think: tailored trousers that offer the comfort of your sweatpants).

With the weather swinging between sunny mornings and chilly evenings, it’s best to accessorize with winter headgear like a cashmere beanie or a wool toque. You can also throw on a lambswool scarf for extra warmth. Nothing is off-limits when it comes to bags—from leather handbags to cotton tote bags to sling bags, we’re seeing gender-neutral styles dominating the streets.

Ahead, scroll through six street style men’s fashion looks that are serving some trendy outfit ideas for winter.

Soft Tailoring + Leather Accessories

Elevate your everyday wear with effortless tailoring and stylish accessories, as seen on this man who wears the comfiest version of tailored wool trousers in grey (that almost double up as joggers) with a sweater and a coat layered with a scarf, all in black. The shiny black brogues and the tan handbag work their charm as statement leather accessories, lending sartorial prowess to this easy-to-put-together street style look.

Pro tip: For days when the temperature hits negative, add a woollen hat and a pair of socks to this outfit.

Structured silhouettes + sneakers

There’s no doubt that a structured single-breasted coat packs a punch, whether it’s paired with formal wear or athleisure. Borrow inspiration from this man who teams a black oversized boxy coat with grey slim-leg trousers and a matching scarf with comfy white sneakers. While stylish shoes can tend to be a bit on the more uncomfortable side you could also add supportive insoles without ruining the style. Bookmark this cozy winter outfit for days you have to work from the office or for running errands over the weekend.

Pro tip: Layer a scarf over your coat, as seen here. Choose from printed and patterned styles for a bolder look.

Minimal monochrome + tote bag

This evergreen staple will take you the least amount of time to assemble. All you need are separates in one dark solid hue to curate a plain yet polished outfit. Take style cues from this man who opts for black-on-black, contrasted by a pair of converse sneakers in black-and-white and the hem of a white shirt. Plus, a carry-all cotton tote bag is perfect for days when you’re on-the-go. This menswear street style look scores high on the sartorial meter for its timelessness and dapper vibe.

Pro tip: A thick woollen toque and a pair of classy sunglasses are must-have accessories for when the sun’s out on cold days.

Colour blocking

Those looking for an experimental outfit can incorporate colour blocking fashion. Equal parts fun and playful, this trend is perfect to wash away the winter blues. Take ideas from this man who colour blocks rust brown with mustard yellow on a palette of neutrals. A rust brown double-breasted coat layered over an oatmeal chunky sweater and black pants harmoniously blend in with the two-toned lace up snow boots, while the toque and scarf in mustard yellow add an overall dramatic appeal.

Pro tip: Try picking complementary hues that are opposite to each other on the colour wheel for an eye-pleasing aesthetic.

Belted wool coat + denim

A good pair of jeans never goes out of fashion. It also makes an ideal companion to an oversized belted wool coat, as seen here. This outfit mixes a variety of textured fabrics including wool and denim for a classic finish. The multi-coloured sneakers and vibrant socks add interesting details to the monochromatic look. This one wins favour for its level of comfort, simplicity, and functionality.

Pro tip: Roll up your jeans for a subtle highlight to showcase your shoes and socks.

Gender-neutral fashion

Genderless clothing is slowly gaining traction, providing that fashion is as fluid as ever. Take tips from this man who accessorizes a bright yellow sling bag with a double-breasted oversized maxi coat worn over a salmon pink jacket and wide-leg trousers. The sunset-hued trainers complement the sling bag, adding a vivid pop of colour to the look.

Pro tip: Add jewellery (like the multiple silver rings seen here) to take your street style vibe up a notch.

Stay updated with the latest street style trends by following Regarding Luxury on Pinterest. Top image by Enrico Labriola, Pitti Uomo