The 4 New Rules of Dressing for Fall

Every product was carefully curated by an Esquire editor. We may earn a commission from these links. Here’s how we test products and why you should trust us.getty images5 min readI know what you’re thinking. Labor Day is nearly here. A brisk morning breeze is no longer a fantasy but an occasional reality. Kids are heading back to school. It’s time for fall, baby!It’s a nice thought, but let’s be real. We’ve got a whole lot of hot days ahead of us before the calendar actually flips over to autumn—and probably a good few after that, too. The seasonal vibe shift might have arrived, but in our brave new world, the weather takes awhile to catch up.So while layering on the fall finery sounds downright enchanting, it’s really a siren song destined to dash you on the rocks of sweaty afternoons and stifling commutes. That doesn’t mean you can’t change up your look, though. You just need to be careful and play by the new rules of dressing for (early) fall.1. Wear White, Forget the Old RuleTheStewartofNY//Getty ImagesNicholas Hoult in a once-controversial post-Labor Day outfit.Have you ever heard of the Straw Hat Riot? (This might sound like a strange aside, but if you follow along, I promise you’ll see how it’s relevant.) It took place in New York City in 1922. Back then, convention dictated that you couldn’t wear a straw hat after September 15. You had to switch to a felt or silk one to align with the shift from summer into fall. If you wore a straw hat after the cutoff, you ran the risk of someone knocking it off your head and stomping it on the street. This was, by and large, a socially acceptable practice. But in 1922, a group of youths decided to start early, on September 13. This turned into a brawl with some dock workers, which eventually escalated into an eight-day riot with reports of mobs up to 1,000 strong roaming the city. There were several hospitalizations and even more arrests.Sounds absolutely ridiculous, right? Well, that’s about how reasonable the old mandate of not wearing white after Labor Day sounds in 2026. While I doubt many of the guys reading this still subscribe to that outdated rule, if you happen to be few remaining adherents, just let it go. White jeans, for instance, are a pretty great way to navigate this liminal style space. Try them with a chambray shirt, a western belt with metal embellishments, and a pair of snuff suede chukkas or loafers. Even a white suit in cotton or linen can look great, provided you knock the stuffiness out of it. That chambray shirt I mentioned earlier would do a good job, as would a blue-and-white striped oxford. If you’re going with a tie, knitted silk in a nice navy blue will keep things from feeling too fancy.Madewell 1991 Loose Straight JeanNow 39% OffCredit: MadewellTodd Snyder Sutton JacketCredit: Todd SnyderLevi’s 501 JeansNow 30% OffCredit: Levi's2. Layer with CarePG/Bauer-Griffin//Getty ImagesColman Domingo proving you can still layer up in the heat—if you’re savvy about it.The temptation to bust out your jackets and sweaters is hard to ignore, but now is not the time. When it still feels like summer in September—or even October—you’re better off dressing like it’s August. Well, sort of.Instead of layering a camp-collar shirt over a tank top, try an overshirt worn open with a tee underneath. (Pro tip: A classic oxford-cloth button-down that makes a great base layer in the colder months also makes a great overshirt when it’s warm.) Instead of shorts, go for a pair of looser trousers that maximize airflow while keeping those calves covered. And feel free to bust out something a little more substantial—but still breathable—when the evening chill settles in. Denim trucker jackets, cotton knitwear, even bits of militaria initially designed for warm weather (like the multi-pocketed jungle jacket) are less likely to make you overheat.As for dressing up: I’ve said it before, and I’ll keep saying it until I run out of breath: Tropical and high-twist wools are your best friend. If it’s made right, an unstructured sports coat made from high-twist wool will have such an open weave that light shines through it when held up to a window. The breeze will flow through just as easily.The idea here is to start moving towards the resplendent fall fits that you can see in your head without getting so covered-up that you start schvitzing the moment you head out the door. Go for lightweight, breathable fabrics that help you achieve that goal. Your mohairs and flannels and sturdy twills will have their time soon enough.J.Crew 1983 oxford shirt in cottonLee Relaxed Fit Rider JacketThe Armoury by Balloon Jacket Wool Balloon Model 3 Sport Coat3. Embrace Autumn ColorsJose Perez/Bauer-Griffin//Getty ImagesIs anyone else suddenly in the mood for a PSL?Bringing in some carefully considered layering is only part of the battle. The thing that brings this all together is a change of palette. Imagine all those pairings I mentioned in the last section colored in yellow and teal and pink and bright blue. Seems positively summery, right? Now wipe your mind clean, and think of them in shades of indigo, olive, burnt orange, and brown. That’s a whole different thing.You might not be able to get away with a felted wool jacket or a heavyweight pair of jeans, but you can tap into the seasonal shift with the right colors. Think of the changing leaves, of course, but also the more somber colors—darker grays, deeper blues—that have traditionally signified the move away from the summer holidays and the business of, well, getting down to business. It doesn’t need to feel funereal. It shouldn’t. Summer may be the time for having fun in the sun, but fall is the season when we get to really start dressin’, experimenting with layers, playing with textures and fabrics, and just having fun with the wealth of options available. If you ask me, that’s well worth celebrating.Tencel Western ShirtCredit: Todd SnyderCorridor Carpenter JeanBuck Mason Field-Spec Cotton Heavy Tee4. Hang onto Your ShortsJean-Louis URLI//Getty ImagesWhen in doubt, trust the Ford.If it’s one of those terrible days when you the temperature is holding steady in the high 80s, and you can cut the humidity with a knife, it’s perfectly acceptable to wear shorts. Probably not on a date. Almost certainly not to the office. But for a morning coffee run? A day at the park? Afternoon drinks with friends? Absolutely. The world has changed. So, too, must our approach to getting dressed. That’s kind of depressing, when you really think about it. But sometimes—like when you get to wear your favorite shorts while unpacking Halloween decorations—it’s kind of fun, too.