Fall Men’s Style Playbook: 7 Plays to Keep You Looking Sharp This Season

Fall is here, and it’s the perfect time to reset your wardrobe. At Union Hall Supply Co., we see fall fashion as a playbook—smart moves and essential pieces that keep you sharp, comfortable, and ready for the season.

In Upstate New York, fall means crisp mornings, layered days, and weekends that go from trail to tailgate to city nights. Your wardrobe has to work harder—warm but not bulky, rugged yet refined. That’s where we come in.

We’ve pulled together the essentials, trends, and answers to your style questions—all in one place. Consider this your fall style playbook.

Play #1: The Go-To Flannel

The flannel is still in style—no “dad mode” here. The key is fit and fabric: skip oversized cuts and choose tailored, elevated options you can layer with henleys, denim, or a canvas jacket. Our pick? The Faherty Heirloom Portuguese Flannel Shirt in Garret Verde Plaid—crafted from premium fabric, it strikes the perfect balance between timeless and modern.

Play #2: Denim Power Move

Medium wash denim is a cornerstone of fall style—polished enough for a button-down, casual enough for a hoodie. You don’t need a dozen pairs; a few quality options worn often are enough.

Our top pick: 34 Heritage Courage Mid-Rise Straight Jeans, versatile, timeless, and built for everyday comfort.

Mix in other pants to elevate your wardrobe: 34 Heritage Beige Honeycomb Textured Weave Pants bring a rugged, textured “working pants” vibe, while Warp+Weft Chicago ORD Straight Pants in Sienna Brown offer a refined, elevated alternative that’s just as comfortable as your favorite jeans. Together, these three pieces create a rotation that keeps your fall looks fresh, functional, and effortless.

Play #3: Sweater Season Strategy

Nothing beats the instant upgrade of a great sweater. Whether it’s a crewneck, half-zip, or chunky knit, choosing versatile neutrals with subtle details makes layering easy and effortless. This fall, don’t settle for a basic sweater—look for pieces with texture, color, or small style touches that elevate your outfit without overthinking it.

Our current favorite: the Faherty Camp Cardigan in Forest Lake. With its cozy texture, versatile fit, and playful personality, it’s the kind of sweater that makes layering exciting. Pair it with denim or casual chinos for a look that’s polished, comfortable, and distinctly you.

Play #4: Boots on the Ground

Fall weather can be unpredictable, but your boots shouldn’t be. A sturdy pair of leather or suede boots adds style, toughness, and function to any outfit.

For versatile, all-season options, go with the Florsheim Anthem Plain Toe Chukka Boot. Its classic three-eyelet design, stacked heel, and choice of rich leather or soft suede make it perfect with jeans or a sport coat for work, date night, or a weekend getaway.

If you want sneaker-level comfort with a polished look, try the Florsheim Monopoli Elastic Lace To Toe Sneaker. With rich leather, detailed stitching, and a cushioned Comfortech footbed, it’s ideal for days when you want to move comfortably without compromising style.

Play #5: The Jacket You’ll Reach For

Every fall wardrobe needs a reliable transitional layer—rugged enough for the outdoors, sharp enough for dinner. Canvas jackets, bombers, or chore coats are the ultimate go-to pieces.

Our favorites this season: the Relwen Pile-Lined Chore Coat, with a classic workwear silhouette and cozy lining for cooler days, and the True Grit Route 66 Drifter Work Jacket, a tough, vintage-inspired jacket that feels broken-in from day one. Both are versatile, durable, and ready to earn “go-to” status in your rotation.

Play #6: The Henley Flex

The henley is fall’s secret weapon—more polished than a tee, more relaxed than a button-down. Wear it solo on warmer days or layer it under flannels, jackets, and sweaters when it’s cooler.

Our top pick: the True Grit Long-Sleeved Henley in Brown. Its rich fall color and subtle stripe lining make it perfect for layering, adding detail without effort. Rugged, relaxed, and versatile, it’s a piece you’ll reach for all season.

Play #7: Strong Accessory Game

Small details make a big impact—a hat, knit beanie, leather belt, or soft scarf can elevate any look.

This fall, swap your summer cap for the Upstate & Chill Perfect Place Patch Hat. With a leather logo and cord detail, it adds a polished, seasonal twist to a casual essential—perfect for crisp days, weekends away, and showing hometown pride.

Your Fall Style Playbook Recap

Fall style is about building a lineup you can count on: versatile, durable, and timeless pieces that work together effortlessly. At Union Hall Supply Co., we’ve curated the essentials to help you play the season in style. Swing by our Saratoga Springs or Albany shops to see the full collection—and upgrade your fall playbook today.

Build Your Essentials Kit
Every man’s closet should start with a handful of versatile players that rotate through the lineup:

  • The Jacket: A barn coat, bomber, or overshirt to handle unpredictable temps.

  • The Sweater: A solid crewneck, quarter-zip, or shawl collar—layered or solo.

  • The Shirt: Flannel or corduroy in seasonal plaids—timeless, easy, and always right for fall.

  • The Pants: Dark-wash denim or heritage chinos; one casual, one polished.

  • The Boots: Weatherproof Chelsea or lace-up boots that transition from workday to weekend.

Your Unspoken Style Questions—Answered by Heidi Owen West (Owner & Style Expert)

  • How many pairs of jeans should I own? Two: one dark, one broken-in.

  • Can I still wear sneakers in fall? Absolutely—just choose leather or suede.

  • Is flannel still in? Always. It’s not a trend—it’s a tradition.

  • Quarter-zip or half-zip? Doesn’t matter. Own one—it’s your secret weapon.

The Bottom Line
Fall is about durability, versatility, and timeless style. The guys who get it right aren’t chasing trends—they’re building wardrobes that can handle the season, year after year. That’s what Union Hall Supply Co. is built on: clothes that feel like they’ve always been yours, but better.

Grab your essentials, step into the season, and consider your fall style playbook complete.

 

Get directions to our Stuyvesant Plaza, Albany, NY location

Get directions to our Saratoga Springs location

 

 

Back to Happenings