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It’s October, folks, which means that we’re undeniably in early fall. The days of rolling out in just a T-shirt are long gone, so it’s time to stock up on transitional jackets. From staple shackets to a thinner take on traditional overcoats, all the notable street stylers are donning midweight cover-ups to keep the cold out and the steez levels simmering. For trans-seasonal layering inspiration, just take a look at these guys...
Stylish guys in transitional jackets featuring a street styler in a black bomber jacket | ASOS Style Feed

Picture: The Urban Spotter

All-black bomber jacket

Out of all the outerwear options in this list, the bomber jacket is probably the most summer-friendly. However, it deserves its place as a transitional must-have because of its lightweight yet sturdy construction. The ribbed collar and cuffs offer up knitwear vibes, while most come with a quilted, satin-feel lining for added comfort and warmth. Opting for one like this in a matte black or navy will have you set deep into the colder months.
Stylish guys in transitional jackets featuring a street styler in a classic leather jacket with red piping | ASOS Style Feed

Picture: Rex

Laid-back leather

For decades, a classic leather jacket has been the go-to item for sartorially savvy guys everywhere. As shown here, the cult item can be thrown on over a subdued outfit to deliver an added edge to the look. Follow in this guy’s footsteps and try and bag yourself one with unusual detailing — notice how he’s nicely matched the red piping to his belt. To top it all off, the insulation a jacket like this provides is second to none.
Stylish guys in transitional jackets featuring a street styler in a camel-coloured mac | ASOS Style Feed

Picture: Imaxtree

Mismatched trench

When it comes to overcoats, a camel-colored trench is definitely up there as the most traditional choice. As an inherently smart garment, it’s a good idea to play around with the way you style it — try combining yours with streetwear as this guy so skilfully demonstrates. The combination of an oversized hoodie, side-stripe tracksuit bottoms and futuristic kicks is expertly offset by his classic trench in a neutral hue. Too slick.
Stylish guys in transitional jackets featuring a street styler in a clean-cut navy overcoat | ASOS Style Feed

Picture: Imaxtree

Great coat

If your outfit’s quite simple, take this as proof that a really good coat is sometimes all you need to set your look off. This guy’s gone for the basics underneath by wearing a minimal gray hoodie and a neat pair of red straight-leg pants. He’s even kept his accessories chilled, with off-white sneakers and a large tote to match, 'cause he knows his coat is packing all the sartorial punches. The angular shoulders, deep pockets and longline shape make this outerwear choice a surefire winner.
Stylish guys in transitional jackets featuring two street stylers in bold coach jackets | ASOS Style Feed

Picture: Rex

Simple shacket

Haven't heard of a shacket before? Well, you’ve been missing out on the ultimate clothing hybrid. Take the silhouette of a shirt and combine it with the added protection of a jacket, and you’ve got the ideal refined layer for the transitional period. Make like these fellas and wear yours buttoned up with rolled sleeve cuffs to smoothly finish off any smart casual get-up. Seek out one in a dark shade or a camouflage print to really nail FW17 dressing.