That first chilly morning, when you step outside and suddenly know autumn has officially arrived, is a pretty special feeling. It’s like nature is nudging you to remember how great layered clothes are, and that excitement kicks off our focus on awesome fall outfits.
This year, the fashion story is all about comfortable, roomier clothes and bringing back some old favorites from past decades. Imagine a cool blend of classic British country style mixed with the relaxed vibe of 90s fashion catalogs. We’re moving away from super skinny looks towards more modern, fuller shapes that still feel polished. These styles just make sense together; it’s a look many of us grew up with, now seen through today’s eyes. Pants and jeans have a nice drape, shirts have enough space for comfort and layering, and jackets complete your look without making you feel like you stepped out of a stiff old photo. Nothing feels overly baggy, but everything is a bit more laid-back and grown-up. We’re not just chasing new trends for the sake of it. As menswear styles have generally become looser, we’re welcoming back things like "classic fit" pants, sturdier shoes, braided belts, and even cargo pants, all updated for today. You might think, "I’ve worn that before," and that’s exactly the point! The fun is in seeing how these familiar styles fit the person you are now, someone who probably has a much better sense of what looks good.
If autumn had a spokesperson, it would definitely be Scotland. It’s got beautiful scenery, crisp air, and weather that practically begs you to dress in layers. We took our photos for this week on a road trip through Scotland, starting in Edinburgh and winding through country roads all the way to the stunning Isle of Skye. The weather there can be a bit unpredictable, and the ground isn’t always smooth, but that’s what real fall is like – not the perfectly styled version you see on postcards.
To kick things off, we’re showing off an outfit that sets the tone for the season. It features a trusty waxed jacket, a soft flannel shirt with a subtle brown plaid pattern, comfortable straight-leg pants in a versatile charcoal color, and sturdy boots that are ready for anything.
Waxed jackets have been popular since the late 1800s for good reason. They’re made from cotton that’s treated with enough wax to keep both rain and unwanted opinions away. They get softer, develop unique creases, and just look better with age. You can find them in longer field jacket styles or shorter trucker jacket cuts.
Forget any outdated ideas about flannel. This is about a classic brown plaid, made from brushed fabric, and cut with enough room to wear comfortably over another shirt. The plaid pattern is low-contrast, so the lines blend nicely instead of being too bold.
Ever wonder what a "5 pocket pant" is? Think of them like jeans, but instead of denim, they’re made from a different fabric – in this case, twill with a little stretch. They have a straight leg and a mid-rise waist, making them stylish yet easy to wear. The charcoal color is incredibly versatile; it goes with everything without clashing.
These are the kind of brown leather boots that can handle a muddy trail or a casual meeting without missing a beat. They’re built to be tough and stylish at the same time.
To pull the whole look together, a field-tested style watch, a simple black baseball cap, and a classic white pocket tee for layering underneath are perfect finishing touches. The watch, in particular, offers a cool nod to how military history still influences modern fashion.