While some men seem to enjoy stocking up on new clothing each season, many tend to think that having a favorite pair of broken-in boots and a few faded plaid shirts in the closet is enough to make them fall-ready. To help inspire a wardrobe refresh, we reached out to three experts from menswear stores across the country for advice on what to invest in this autumn. From versatile layers to luxurious pieces, here are their must-have picks for this season.


“The workers jacket is the perfect addition to a man’s fall closet because it’s super versatile,” Ian Dillard, co-founder and manager of contemporary menswear store Quattro Tizi in Charlottesville, Virginia, says of the functional yet undeniably cool lightweight coat he can be seen sporting here. “As the seasons shift, your to-do list grows: parties, hikes, meetings, house projects. We love the French Work Jacket from Le Mont St. Michel because it will keep you looking put together through it all.”

For occasions when you’ll need to look a little more polished, “A nice textured sport coat will elevate a fall wardrobe dramatically,” says Alexa Womack, operations coordinator and textile specialist at Huntsville, Alabama-based men’s clothier Roosevelt & Co. “There has been a resurgence of the classic center vent on a lot of casual coats to give a simpler silhouette. Southwick is a favorite for us with their hook vent. And this season we were able to create a completely unlined coat with a single vent, which will serve as a nice fall casual piece,” she adds.

“There are so many versatile outerwear pieces out for fall,” Lindsay Morton Gaiser, vice president and GMM at menswear store Andrisen Morton in Denver, Colorado, notes. To really take your closet up a notch, “You can go for a super luxe cashmere piece, like this one from Brunello Cucinelli with a stand up collar and open patch pockets. While this piece is an investment, you will find its versatility makes it an item that you will want to wear again and again,” she says.


“We’re all about layering here at Roosevelt and Co., and the crew neck in a lightweight knit is the perfect silhouette for this season,” Womack says. “There has been an emphasis on colored knits that transition from a simple five pocket to an added layer beneath a sport coat this season, and for us it’s the little details that will make this work.” One of the store’s favorites is the Burgundy honeycomb crew neck with ribbed neck, hem, and sleeves from Stone Rose. “It is the perfect color that embodies all things fall, but also transitions into a subdued under layer,” she explains. Gaiser agrees about the importance of knitwear, either worn under tailored clothing or alone. “Whether it be a long sleeve pique full button or a short sleeve jersey, this item is a very important staple in a man’s closet. Fedeli is one of our favorite brands,” she says.

“A plaid button-down is a great way men get to bring color and pattern into their wardrobe,” Dillard says, adding that since a great plaid shirt is a staple that will continue to be in style for years to come, it’s well worth the investment. His current favorite in-store checked options include the cozy, textured Corridor Blanket Plaid in Clay and the soft, neutral-hued Faherty Stretch Seaview Flannel Evans in Range Buffalo.


“Looking at the color palettes for this season, we noticed a lot of rich earth tones,” Womack says, adding that she and her Roosevelt & Co. colleagues are loving the subdued hues—especially when it comes to the pants. “A staple pair of 5-pockets is going to be a versatile component when it comes to your wardrobe,” she advises. “Pair them with a basic tee or dress them up with a button down and sport coat; they’ll look good through it all.” One of Roosevelt & Co.’s favorite 5-pocket options is the Billy Reid rubber corduroy, which features a smaller wale than a traditional cord. “They offer you the look of a corduroy, but feel more like your traditional twill,” she says.


“It’s a sneaker world out there right now, so you cannot go a season without elevating your sneaker game! Leather, canvas, dressy or casual, invest in one—or four—pair every season,” Gaiser says, adding that they are acceptable to wear with most anything for fall. “Our current favorites are the Zenga Triple Stitch Slip-On Sneaker and the Di Bianco Deco Reverse Sombrero.”

For a timeless piece that can be paired with any outfit, Dillard recommends a Chelsea boot. “From that holiday gala with a suit to weekends on the farm, they make the best slip-on shoe. For a dressier pair, we like the To Boot New York Shelby in Brown Suede. Our casual, everyday choice is the Blundstone Dark Olive Suede boot,” he says.

Photography by Kadie Pangburn for Roosevelt & Co. Roosevelt & Co. is featured in The Scout Guide Huntsville. Quattro Tizi is featured in The Scout Guide Charlottesville. Andrisen Morton is featured in The Scout Guide Denver.