5 Men’s Fall Fashion Trends We’re Shopping at Macy’s for 2026
Fall is always one of our favorite seasons to dress for. The colors get better, layers come back, and the pieces we haven’t touched all summer suddenly make sense again.
We’ve already shared our Men’s Fall Capsule Wardrobe for 2026 and our 12 Men’s Fall Outfits, so this one is more about the trends we’re seeing come through this season and the pieces we’d actually wear.
We went through Macy’s men’s selection and picked five trends that feel very fall 2026 without being difficult to work into what you already own: rugby shirts, Fair Isle sweaters, overshirts, long-sleeve Henleys and flannel shirts.
1. Rugby Shirts
Rugby shirts are back in a big way this fall, and we’re not mad about it. They have that slightly preppy feel we both like, but they’re also just easy to wear. Jeans, chinos, loafers, sneakers. You really don’t have to think too much about it.
The Polo Ralph Lauren Men’s Iconic Rugby Classic-Fit Polo Shirt is the most traditional of the four, with the bold stripes and contrast collar you’d expect from a classic rugby.
The Weatherproof Vintage Men’s Cotton Cashmere Rugby Polo Sweater feels a little softer and more dressed up, while the Tommy Hilfiger Men’s Waffle Structure Rugby Sweater brings in more texture.
We also like the Lands’ End Men’s Long Sleeve Cotton Rugby Sweater Polo, especially if you want something classic that still feels casual.
This is probably one of the easiest trends on the list for us because rugby shirts are already something we wear.
2. Fair Isle Sweaters
Fair Isle used to feel like something you pulled out in December. Not so much anymore.
This year we’re seeing more browns, navy, cream, rust and muted blues, which makes it feel much more wearable through fall and not just around the holidays.
The Polo Ralph Lauren Men’s Fair Isle Wool Regular-Fit Sweater is a good one if you want something that can be dressed up a bit with a collared shirt underneath.
We also like the Polo Ralph Lauren Men’s Fair Isle Wool Mockneck Quarter-Zip Sweater, which feels a little more current and probably closer to how we’d wear Fair Isle ourselves.
The Aubin Men’s Fair Isle Crew Neck Wool Sweater has a more traditional feel, while the Hope & Henry Organic Half Zip Intarsia Pullover Sweater brings in those warmer fall tones.
These are the kind of sweaters we’d keep the rest of the outfit simple with. Dark denim, trousers, loafers and done.
3. Overshirts
Overshirts are a great versatile piece to use as a layer. They’re useful when it’s not quite cold enough for a proper jacket, but you still want another layer. We wear them over T-shirts, Henleys and polos, and they’re easy to dress up a little with trousers or darker denim.
The REISS Men’s Thom Sueded Interlock Jersey Regular-Fit Overshirt in Taupe is one of the more polished options here and would work just as well for dinner as it would during the day.
The Vintage & Black Men’s Twill Overshirt Jacket is more casual and would be an easy one with jeans and a simple tee.
We also picked the REISS Men’s Thom Sueded Interlock Jersey Regular-Fit Overshirt in Black, which is the same clean shape in a darker color and feels a little sharper.
Then there’s the REISS Men’s Penge Brushed Wool-Blend Overshirt, which is probably the dressiest of the four and one we’d wear with a fine knit or polo underneath.
Overshirts also fit right in with the layering pieces we included in our Men’s Fall Capsule Wardrobe for 2026, which is probably why we keep finding reasons to wear them.
4. Long-Sleeve Henleys
Henleys are one of those things that never really disappear, but they definitely feel more noticeable again this fall. We like them because they’re a bit more interesting than a basic long-sleeve T-shirt, especially when there’s some waffle or thermal texture.
The Tommy Hilfiger Men’s Waffle Texture Henley Shirt is probably the cleanest of the group and could easily work with trousers as well as jeans. The X-RAY Men’s Long Sleeve Henley T-Shirt is more straightforward and makes a good everyday layer.
The Weatherproof Vintage Men’s Variegated Microstripe Waffle Henley T-Shirt has a bit more texture, and the Lucky Brand Men’s Birdseye Thermal Henley Long-Sleeve T-Shirt is the most casual of the four.
For us, Henleys work best in cream, charcoal, navy and other neutral shades. They’re easy to layer and don’t fight with whatever you’re wearing over them.
5. Flannel Button-Ups
Flannel for fall is hardly groundbreaking, but the way we’d wear it now is a little cleaner than the old jeans-and-boots version. Think dark denim, chinos or trousers, simple sneakers or loafers, and let the shirt bring in the pattern.
The Weatherproof Vintage Men’s Slub Flannel Plaid Shirt has those orange, navy and cream tones that immediately feel like fall. The Quiksilver Men’s Penmar Check Flannel Shirt goes a little greener and more muted.
The Hurley Men’s Santa Cruz Seaside Flannel Long-Sleeve Shirt is more neutral in cream, black and brown, so it would be easy to wear with just about anything. Then there’s the Weatherproof Vintage Men’s Button-Front Flannel Shirt, which leans into rust and brown and feels exactly right for the season.
Flannel is probably the easiest trend here to add back into the rotation if you haven’t worn it in a while.
What We’re Wearing This Fall
What we like about all five of these trends is that none of them feels like a huge departure from the way we already dress.
Rugby shirts, Fair Isle sweaters, overshirts, Henleys and flannel are all familiar. The difference this year is in the colors, fabrics and how they’re being styled.
They also work well with the pieces we already included in our fall capsule wardrobe and the outfits we’ve been putting together for the season. You can add one or two pieces and get quite a few new looks out of what you already own.
We’ve put all 20 of our Macy’s fall picks together in one place, including every piece featured here.
