Stylish and Versatile Fall Wardrobe Essentials Any Man Will Feel Comfortable In

It’s not a secret that jackets are one of our favorite fall essentials, and we’re already planning to “borrow” this topper once opportunity strikes. Cut similarly to a denim trucker jacket and lined with a cozy sherpa fabric, this corduroy number will become a staple in his fall wardrobe for years to come. 

As the leaves begin to fall and the temps fall with them, he’ll need to start trading short sleeves for something warmer. Instead of a plain ol’ long sleeve, opt for a waffle thermal to keep him toasty. The patterned weave retains heat better than others, and this one from Everlane is made from luxuriously soft organic cotton and comes in six different colors.

Believe it or not, skinny jeans are dead for men, too. We haven’t quite swung back around to pleated dad jeans yet, but a baggier fit is certainly the look du jour. These ones from J.Crew are made of a heavy-weight Japanese denim that will mold to his body shape over time, and reviewers say that these are reminiscent of classic workwear styles. They’re roomier around the calf and offer a flattering fit, but many reviewers warn that the waist runs on the larger side, so take this into consideration when ordering. 

No matter how you wear a button-up — open as a layering piece, fully buttoned to the neck, or with the sleeves casually pushed up to the elbow — a solid-colored button up is a wardrobe workhorse. We always recommend white because it truly goes with everything, from jeans and a graphic tee to slacks and a tie. 

They may not be top of mind while you’re getting dressed, but socks are an important part of your wardrobe — and not just because of that sliver that shows between your shoe and pants. This pair from Bombas is thin enough to wear with dress shoes but not too thin to wear with sneakers, and they have a cushioned footbed to keep you comfortable while commuting or just wearing them around town.*

Khaki  pants will never go out of style, but a utilitarian take is currently trending. More casual than chinos but sleeker than cargos, these field pants are made from 100 percent cotton and have a sturdy herringbone weave that adds a subtle pattern. Alex Mill modeled this fit from military workwear so there are tons of useful pockets and an adjustable waist for a custom fit. 

Consider this half-zip a reason to keep stealing his sweatshirts. The fabric is buttery soft and has a brushed, fleece-like interior, so he’ll love how great it feels on. He’ll be able to layer it over a T-shirt for errands and if he tosses it over a button-up, the end result will be a comfy, but elevated outfit. 

Formal occasions call for a sleek shoe, but that doesn’t mean they have to have laces. A vintage-inspired penny loafer is dressy enough to wear to a wedding or business meeting, but look especially dapper when peeking out below jeans. And they require much less fussing to put on than the average dress shoe. Don’t be surprised if they start wearing these comfy, glamorous slip-ons as slippers. 

Waterproof and stylish? These boots marry the best of both worlds. The tough leather on these can handle rain, snow, and slush with ease, but they look so much better than your average winter boot. Commerce editor Katie P. gave her boyfriend a pair of these a couple of years ago, and he wears them nearly all season long, saying they’re comfortable on long walks and took nearly zero time to break in.

If the shoes he wears to mow the lawn are also the ones he wears to get drinks with friends, it’s probably time for a new addition to his shoe collection. A leather sneaker is incredibly easy to style with jeans or joggers for day-to-day wear, but they’re also sleek enough to wear with trousers in a casual office. 

So many of us have strayed away from the dreaded “hard pants” that don’t have a built-in drawstring, but sometimes dressier pants are necessary. During those rare occasions, it’s best to have a belt that not only holds up the pants, but provides a visual break in the outfit should their shirt be tucked in. Leather belts are always a timeless option because they last for years, sometimes decades, and the patina a well-made buckle develops over time only makes them look better with age. 

It may seem ridiculous to spend more than a few dollars on a white T-shirt, especially if you’re prone to spills and stains. But you really do get what you pay for in this department. This heavyweight cotton shirt is opaque, won’t stretch out around the neck easily, and drapes better than cheap styles you buy in bulk. 

Both Molner and several of the men on the Katie Couric Media team approve of this athletic pant-trouser hybrid. Made from a stretchy, sweat-wicking material, these don’t require ironing to be wrinkle-free, and they are dressy enough to be worn to work or on the golf course.