Fall Menswear For Oceanside Escapes

September 8, 2026 Vacationer Staff

Don’t let the name fool you. Surfside Supply Co. goes way beyond Summer style and into the cooler seasons—with its signature comfy and relaxed fits finding a new expression this season.

We’ve picked some of our favorite, unfussy, Fall fashion items from this Dad-founded brand, and paired them with some of your favorite seaside Fall destination ideas!

Bobby Cashmist Fleece Quarter Zip

It’s sweater weather! But this one is light and wonderful for layering. The Bobby is a classic quarter-zip in ultra-soft, lightweight Cashmist fleece with easy machine-wash care. We love it in Slate Blue Heather. It packs well and rolls up to nothing, plus it looks great worn over a white T-shirt.

Our vacation idea: Santa Monica, California

If you’re visiting Los Angeles’ favorite resort this Fall or Winter, be sure to pack this. It’ll keep you cozy and stylish for a night out in Santa Monica, at a popular spot like The Abbey Food & Bar, catching up with old friends. Drop into Mattie’s WeHo. Or take the coastal highway up to Malibu for a change of scenery.

Brian Washed Twill Plaid Shirt

Perfectly relaxed, this top-selling casual collared shirt in a slightly broken-in washed cotton plaid has that cuddly vibe we love about Fall. Classic details include a single chest pocket, shirttail hem, and button cuffs. Made from 100% soft cotton (80% is recycled!), wear on its own, over a T-shirt, or under a jacket in cooler temperatures. It looks good unironed. It’s a great layering piece for vacation. The sage-and-russet color combo is the perfect fashion choice for this time of year and complements most skin tones and colorings.

Our vacation idea: Provincetown, Massachusetts

While famous for summer, autumn in P-Town is a well-kept secret. The historic town becomes incredibly peaceful, framed by gorgeous New England Fall foliage. October features iconic community gatherings like Fantasia Fair and Friday Gallery Strolls. You can enjoy relaxed whale watching, uncrowded strolls down Commercial Street, and excellent dining without the wait times. These are well-made, comfortable items that pack perfectly and are low-key and reliable for

Butch Cashmist Crewneck in Camel Heather

Think of it as a long-sleeve tee with varsity touches like a V-insert under the collar and ribbed trim on the crewneck, cuffs, and waist. The new Cashmist fabric is super-soft and airy, like cashmere, with machine-washable ease. You’ll love this top for lazy days and casual social engagements alike. This long-sleeve tee dresses up surprisingly well, looking good underneath a leather jacket or blazer. And the simple neckline invites your favorite scarf on cooler nights by the water.

Vacation idea: San Francisco, California

Something about this refined top’s simplicity screams a day in the City by the Bay—perfect for a foggy night and a nightcap around the fire pit at The Presidio’s lodgings, for example.

Damian Knit Twill Straight Leg Pant in Charcoal Heather

A comfortable everyday pant with a clean, straight-leg fit, the Damian Knit Twill Straight Leg Fleece Pant is made from a soft, stretchy blend for comfort and ease of movement. These are not tracksuit pants; they’re not jeans; they’re not heavyweight khakis either. They’re like the perfect combo of all three! Single-button waist, with an adjustable drawstring waistband, and practical and deep side pockets, with one also in the back. Designed for an effortless, flattering fit and feel, whether you’re walking, hiking, or going out to dinner. They don’t need pressing and roll up without wrinkling, making them easy to pack.

Vacation idea: Ogunquit, Maine

Often called Maine’s answer to Provincetown, this charming, artistic coastal community flies its pride flags high year-round. Take a romantic fall walk along the Marginal Way—a cliffside path overlooking the crashing Atlantic waves—and visit the local art galleries. Nearby, you can explore towns in western Penobscot Bay, like Rockland, for fresh and innovative farm-to-table dining. These pants are a great choice if you plan to be hopping on and off small craft vessels.

Danny Full-Zip Cashmist Fleece Hoodie in Dark Brown Heather

The hoodie you’ll reach for again and again. The Danny Full-Zip Hoodie is silky-soft Cashmist fleece for lightweight comfort and easy layering. It features a full-zip front, kangaroo pocket, and Surfside signature patch logo. Elegantly made but with an effortlessly laid-back feel.

Vacation idea: Rehoboth Beach, Delaware

Affectionately known as an East Coast queer oasis, Rehoboth remains lively well into the Fall. September and October bring beautiful, warm beach days without the suffocating summer traffic. The town boasts a bustling boardwalk, fantastic tax-free shopping, and several long-standing gay bars and restaurants near Poodle Beach. Relax and grab an unpretentious break before heading into the insanity of the festive season.