A good flannel can handle most of fall’s best plans, from Saturday coffee runs or to a drive in the country to lingering around a fire when the sun goes down. Tommy Hilfiger’s version comes in brushed cotton twill with an all-over tartan check, button-down collar, and regular fit that makes it easy to wear on its own or over a T-shirt. The shirttail hem and rounded cuffs keep it polished without making it precious.
Some fall nights call for a jacket with versatility. Think game day, dinner downtown, or drinks that were supposed to be one round. This relaxed-fit varsity jacket pairs a premium wool-blend body with smooth leather sleeves, then finishes the collegiate shape with a baseball collar, snap buttons, and striped rib-knit trim. It has enough structure to pull together jeans and a tee, but the relaxed fit keeps it firmly in weekend territory.
Advertisement – Continue Reading Below
The white shirt earns its keep when fall calendars start filling up. This stretch-cotton version works for the office, a date night, or those mornings when you need to look presentable before the coffee kicks in. Wear it with tailored trousers for a cleaner look, or loosen things up with jeans and sneakers. Basically, it’s the shirt you’ll be glad is hanging there when you have five minutes to get dressed
When a T-shirt feels too casual and a dress shirt feels like overkill, reach for an Oxford stripe. It’s the sort of shirt that makes a crewneck sweater look sharper, gives a chore coat some structure, and can carry an outfit on its own. The stripes add just enough personality to keep a fall uniform from feeling like, well, a uniform.
Advertisement – Continue Reading Below
A burgundy turtleneck is a strong move for the first cold weekend of the season, when a sweatshirt won’t quite cut it and a full coat feels premature. This wool cable-knit sweater has the texture and weight to anchor a pair of dark jeans, while the high neck gives the look a little more presence. Wear it to a gallery opening, a long lunch, or anywhere else where you want to look like you gave the outfit some thought
Relaxed jeans are especially useful once fall arrives and every outfit starts accumulating another layer. The River Relaxed Charlie has the roomier silhouette that looks right with a chunky sweater, flannel, or varsity jacket, giving those heavier pieces some breathing room. Take them to the kind of event where comfort is part of the dress code
Advertisement – Continue Reading Below
Every fall outfit needs a reliable sneaker, particularly when the day involves more walking than you planned. The Tommy Hilfiger Tribeca has a clean, low-profile shape that slips easily under relaxed jeans, chinos, or a pair of cords. Wear them for a Saturday in the city, a game-day afternoon, or the airport when your carry-on is already doing enough heavy lifting.
Barry Samaha is a writer, editor, and creative consultant working across style, culture, art, and design. He has overseen commerce at Robb Report and held editorial roles at Esquire, Harper’s Bazaar, and Surface. He also directed U.S. editorial operations at Tod’s Group Digital. His writing has appeared in Departures, Forbes, Paper, Glamour, ELLE, South China Morning Post, and more. He is based in New York City and never seems to have enough closet space for all his shoes.
