4 Outfits to Try This Fall/Winter 2026

I’ve got all the outerwear I need. Still, I want to avoid looking the same every year when it comes to fall and winter outfits. With mild winters continuing, many people probably don’t feel the need to buy a new coat or down jacket to serve as the centerpiece of their look, but they still want to add a fresh touch to their style.In fact, there’s a way to completely refresh the look of your fall and winter outfits without even changing your outerwear. In this article, using the latest street style snaps as a guide, we’ll introduce men’s styling techniques for Fall/Winter 2026 that let you take a small step forward while making the most of your existing wardrobe!

A Small Challenge for Fall/Winter 1Beyond Y2K.Incorporating the ‘Narrow Stole’ Inspired by the Eddie Slimane Era at Dior

The narrow stole brings to mind the slim tailoring and edgy, rock-inspired vibe popularized by Dior Homme during the Eddie Slimane era.While they share the decorative quality of a cravat or ascot tie, they aren’t bound by shirt collar styles or specific tying conventions. They aren’t as formal as a tied tie, nor do they emphasize warmth as much as a typical scarf. It is this exquisite balance that creates an understated allure around the neck.Why not keep an eye on this as a preview of the next trend set to follow the Y2K boom?Domenico Gianfratte pairs a brown short blouson and loose-fitting slacks with a leopard-print narrow stole tied in a single knot. While such patterns can easily look out of place with lighter layers, they’re less likely to stand out awkwardly during the fall and winter when layered under outerwear or knitwear.

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The shape of the scarf Ms. Janhufrate is wearing is likely diamond-shaped. I recall that Altea was promoting this style before the pandemic, and it was gaining attention among fans of Italian fashion.Personally, I prefer the masculine look of casually draping a large scarf—like the ones in Hermès’s “Losange” collection. Since scarves come in such a wide variety of designs—including patterns, materials, and shapes—I think it’s fun to hunt for your favorite designs among vintage pieces.

A Small Challenge for Fall/Winter 2A Serious Yet Sporty Mix: ‘Long Coat’ & ‘Cap’

Here’s a mix-and-match style suggestion: pairing an authentic long coat with a sporty cap.Since a long coat creates a substantial look—for better or worse—simply by throwing it on, adding a cap to bring a sporty, lighthearted vibe helps strike the right balance in the overall volume of the outfit. In recent years, 5-panel caps featuring retro graphics have been steadily gaining popularity.With a linear silhouette that’s a bit different from the 6-panel style—the original baseball cap—they create a contrast with the curved contours of your face, which has the added benefit of making your facial structure look sharper. This combination is recommended for anyone who wants to enjoy a change of pace from their usual, more formal coat style.

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Inspired by the 911 Carrera T (Type 992), this cap was designed by L’ART DE L’AUTOMOBILE, led by Arthur Kar. Both the choice of motif and the silhouette are stylish.Not only are caps relatively affordable, but many feature designs with meaningful messages, so I think part of their appeal lies in the joy of choosing one that resonates with your values and mood. I also recommend checking out shops with a wide selection of vintage caps, such assowhatvintage in Shimokitazawaor ALLCAPS in Hachioji, to find your very own favorite.

3 Small Challenges for Fall/WinterThe key is that it’s not obvious at first glance. ‘Two Unexpected Accent Colors’”

Even a single accent color can transform an outfit, but placing the same color in two separate spots makes the styling look intentional rather than coincidental.Furthermore, if you choose an unexpected item for one of those spots, you can add a touch of playfulness without being too obvious. A great example is this outfit, which incorporates a fluorescent yellow hue into both a narrow scarf and an iPhone case.The color around your neck is always in your line of sight, while the color of your smartphone appears only the moment you take it out. The idea is that this time lag in visibility creates a subtle, connoisseur-level touch that makes people realize, “They’ve really coordinated that well.” It’s also worth noting how the outfit keeps most of the clothing in neutral colors, centered around a brown outerwear piece and white pants.

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Apple’s official cases come in a wide variety of colors, so I think they’re the perfect choice for experimenting with accent colors.It takes a bit of courage to incorporate neon or vibrant colors into your outfits, but it’s much easier with a phone case. Try coordinating the color with accessories you already own—like a scarf, socks, or a detail on your sneakers—to subtly create a sense of cohesion in your everyday look. It’s also fun to think about styling not just your clothes, but the items you carry with you every day.

4 Small Challenges for Fall/WinterNow that wide-leg pants are all the rage, stand out with 'winter pants' that give a cozy look

In fall and winter, the focus tends to be on outerwear. However, it’s often the fabric of your pants that actually determines the overall impression of your outfit.Even if you’re wearing the same coat or jacket as last year, simply adding a brushed texture or some texture to your lower half can completely refresh your overall seasonal look and silhouette.Options are plentiful, ranging from corduroy and tweed—which are easy to incorporate into a city-chic look—to down, fleece, faux fur, and brushed-lining sweats. While winter fabrics can make your legs look thicker due to their bulk, wide-leg pants have become a staple, so there’s no need to forcefully slim down that volume—which is one of the reasons they’re so popular right now.

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Personally, winter is my favorite season for choosing pants fabrics. Whether it’s the width of the ribs in corduroy, the fuzzy texture of wool, or the volume of fleece and quilting—even with the same silhouette, the impression changes drastically just by switching the fabric.In the past, I used to avoid thick pants because they looked a bit frumpy, but now that wide silhouettes are the norm, they’re actually easier to incorporate into my wardrobe. I think it’s worth taking the plunge and trying out a bold Sherpa fleece fabric like the one worn in this snapshot.