As the leaves change and the air turns crisp, fall is the season to embrace layers, rich textures, and versatile outerwear. But for tall guys, finding the right fit can be a challenge. The good news? Several brands deliver when it comes to fall essentials in tall sizes. Let’s break down some top picks and style tips to keep you looking sharp this season.
Westport Big & Tall
Westport is a go-to when you want both classic and refined looks. They carry tall sizes from two of my favorite brands like
Peter Millar and
Cutter & Buck, making it a one-stop shop. Their flannels, sweaters, and vests are perfect for layering without feeling boxy.
Best for: Business casual layering and elevated weekend wear.
Tall Guy Note: I haven’t tried Westport’s Brand Label clothing yet, but there are some good looks
Eddie Bauer
Eddie Bauer nails
rugged outdoor style with plenty of tall-friendly options. Their flannels, quilted jackets, and long-sleeve henleys are built for guys on the move. Plus, their tall outerwear is cut with extra sleeve and torso length, so you won’t get the dreaded “short jacket” look.
Best for: Weekend hikes, casual layering, or tailgating in comfort.
Tall Guy Note: Sizing can be a bit fickle with Eddie Bauer, either in sleeve length or how it fits around your shoulders and chest, so I recommend ordering a couple of sizes
L.L. Bean
Known for durability and timeless style,
L.L. Bean makes tall sizes that actually hold up season after season. Their
Chamois Shirts are legendary, and their outerwear (think barn coats and insulated parkas) is built for real fall weather.
Best for: Classic New England-inspired fall style.
Tall Guy Note: Similar to Eddie Bauer, sizing on jackets, long sleeve shirts, etc… can definitely fit differently and recommend getting multiple sizes to try on.
Polo Ralph Lauren
Polo brings polish to fall layering. Their tall sweaters, half-zips, and button-downs are perfect if you want something sharper than rugged flannel. They’re especially strong in
sweaters and long-sleeve knits that elevate casual outfits.
Best for: Smart-casual and dressier fall looks.
Tall Guy Note: I’m a big fan of their long sleeve hoodie!! Tall size of course.
Cutter & Buck
Blending sport and lifestyle,
Cutter & Buck offers tall-friendly pieces that transition well from work to golf course to weekend. Their tall
long-sleeve polos,
quarter-zips, and
outerwear are versatile staples.
Best for: Polished yet relaxed style.
Tall Guy Note: I’m becoming more and more of a fan of their stuff and recommend the XL Tall, which fits nice!
Whether you’re layering up for a weekend football game, heading to the office, or enjoying crisp evenings outdoors, these brands deliver fall staples that actually fit tall guys the way they should.