Do you feel that? That ever-so-subtle, brisk hint of a chill in the morning air? Well, depending on where you live, maybe not. And even if you answered yes, chances are you’re just as delusional as the rest of us fellas wishing for fall to hurry its ass up so we can really start dressin’ again.
But in truth, autumn is nearly just around the corner. In about a month or so, leaves will start turning and your girlfriend is probably going to be faced with an urge to rewatch Gilmore Girls.
But what does this mean for men, exactly?
It’s not exactly a secret that autumn is arguably many fashionable men’s favorite season to get dressed. The just-cool-enough-to-layer temperatures let you start adding more to your favorite outfits, as opposed to constantly having to work with less during the summer.
But beyond sheer functionality, and the golden rule that almost every outfit benefits from a damn cool jacket of some kind, there remains a ton of opportunity to embrace the sartorial aesthetics of fall.
At a glance, the season’s aesthetics seem easy enough to identify. Lots of earth tones. Think of browns, taupes, greens, and the like. However, there’s more to it than just a familiar color family. Fall aesthetics are among some of the most interesting, classic, and perhaps most importantly, romantic looks a guy can strive for.
There’s a reason so many iconic rom coms and comfort sitcoms are commonly set in or associated with the season. It’s the perfect time of year to dress nice, take an evening stroll, and casually confess your undying love or something.
So, in an effort to capture that very spirit, we’re breaking down 5 of the best fall fashion aesthetics that both you and the women in your life are bound to love.
The Male Rom Com Lead
Perhaps a bit on-the-nose for the title of this article but nonetheless a great aesthetic to strive toward, the male rom com lead look is essentially a loose amalgamation of micro-aesthetics and classic outfits worn by the likes of Billy Crystal in When Harry Met Sally (1989), Tom Hanks in You’ve Got Mail (1998), and others.
This look generally relies on basic clothing dialed up a notch in terms of quality, texture, and fit.
For example, take Billy Crystal’s famed fit from the aforementioned When Harry Met Sally, involving an ultra-chunky white cable-knit sweater that billows generously at the sleeves, paired with a pair of classic light-wash denim and white sneakers.
This look is pretty easy to recreate on paper, and in recent years it’s become somewhat of a trend to emulate, but pay attention to the details. For the sweater, go big. Go textured. And get jeans that make your ass look great.
Another loose template to get the male rom com lead autumn aesthetic down pat is to accessorize in the right way. Experiment with scarves wrapped haphazardly over elevated classic outfits involving pleated chinos, oxford shirts, wool sweaters, cardigans, all in a range of earth tones for good measure. If you’re feeling extra sophisticated, consider a turtleneck, even!
Or, go for a pop of primary color here and there. A bright red shetland sweater or cashmere scarf brings a lot of main character energy to otherwise humdrum fits inspired by peak 90s fashion.
The “Eclectic Grandpa”
Sometime around fall 2023, fashion influencers seemingly invented this somewhat awkward term out of nowhere. In truth, it really just describes the sort of put-together whimsy you might associate with a sophisticated New England grandfather who drives a Subaru and wears L.L. Bean duck boots.
Those boots ain’t a bad place to start. But this aesthetic is all about showing off a sort of warm personality through the abundant use of texture and the occasional dose of fun patterns.
Try pairing corduroy pants in earthy tones like brown, tan, and green with quality flannels, work shirts, and wool knitwear. Shaggy Dog sweaters by J. Press are a great option in this regard. Barn jackets, chore coats, and similar pieces work really well here, too.
You can have fun with oddly patterned socks here, often with a motif of ducks, dogs, deer, or whatever, really. Pair them with duck boots, boat shoes, moccasins, and other New England staple footwear.
Scarves, beanies, and a good outdoorsy watch are all great accessories that truly bring this niche aesthetic to life. If you’ve ever been worried about looking old, don’t – this is the type of old-timer look that’s honestly a lot of fun to try out at any age.
The Country Gentleman
When in doubt, reach for tweed. Autumn weather presents suitable temperatures to wear heavily textured wool and corduroy fabrics, and the English/Scottish countryside style is a reliable blueprint that’s surprisingly easy to adapt for more contemporary settings.
If you’re not feeling a full tweed suit (which is a sick option, mind you), consider going for corduroy trousers paired with a tweed sport coat, each in varying but complementary shades of brown, green, or gray.
Layer the jacket over an oxford cloth button down and/or thick wool knit of some kind (Fair Isle knits are especially great), and strap on some brown leather boots or bluchers/derbies.
Unless you’re a bit further along in your years, we generally recommend going full Scottish country gentleman and avoid the temptation to round out the look with a tweed flat cap. They’re nice pieces of headwear, but a bit hard to pull off with the right intention.
Instead, accessorize with scarves, fine wool or leather gloves, and maybe an embossed leather belt.
For rainier conditions, this aesthetic has two great options that will bring an element of distinguished sophistication to your ensemble, not to mention make your overall silhouette more attractive.
When the weather turns gloomy, pop on either a waxed jacket (like Barbour) or a lined trench coat. Both mesh well with corduroy and tweed garments and exemplify a certain casual elegance born from UK tradition.
The Ivy Style Academic
Ivy style and the loosely-defined “dark academia” aesthetic are always a fine choice, but they shine even brighter during the autumn months. Films like Dead Poets Society (1989) and The Holdovers (2023) are rife with great fall-winter menswear, and worth incorporating into your own wardrobe.
Plus, women love a smartly-dressed man. Just make sure you’re well-read enough to talk the talk, too, of course.
A lot of the fundamental garments for this aesthetic are very similar to those mentioned in the country gentleman aesthetic – that is, it has a heavy reliance on tweeds, corduroy, and knitwear. Only, there’s an extra degree of polish present here, with accessories like reading glasses, leather messenger bags, and knit ties making some appearances.
Try starting with a pair of pleated chinos or corduroy pants, and add an OCBD. Then, get either a knit and/or striped rep tie, and wool sweater, cardigan, or even a sweater-vest.
Lately, add a jacket in either tweed, corduroy, or a navy blue blazer (bonus points for gold buttons). For footwear, stick with derbies, loafers, mocs, or something similar. Classic sneakers like Converse Chuck 70s can work as well!
Remember to work around earth tones to lean into that maximum autumn effect. Some variation is totally allowed, but those colors will communicate the seasonal intention all the more so.
The Autumn Professional
Say you have an office job – chances are the dress code ranges somewhere around the middle of business casual. You want to look professional, but allow your fashionable standards to shine through. Plus, there’s always the chance you’ll be trying to meet eligible women after work hours.
Lucky for you, it’s easy to incorporate autumnal fashion into your corporate wardrobe to great effect.
Earth tones are never a bad place to start, but you don’t have to lean so heavily into them if you don’t want to. As an alternative, you can play with primary colors, grays, black, and whatever else really suits your fancy. Just remember though, earth tones will always make your outfit feel more in-tune with fall from the get-go.
Chinos, cords, and dress slacks are all fair game, and even better when they’re adorned with details like pleats or patterns like herringbone. You can even spring for some tweed trousers, if you feel so inclined.
Oxford shirts and wool sweaters are your best friend here, but you also can’t go wrong with a cardigan to get a perfect layering effect without a jacket.
If your office permits jeans, try to go for a darker wash of denim – it’s more attuned to fall.
Sport coats are a great way to continue the layering effect. Consider getting a tweed jacket in brown or gray for maximum versatility.
Accessorizing is easy in the form of scarves, too. You can go as basic or as wild as you want really, since it’s only really worn when going to and leaving the office.
For outerwear, a wool overcoat of substantial length will do your image absolute wonders. For something that’ll best work across various levels of formality, consider a raglan wool coat, defined by the unique diagonal cut of the sleeves. Just like sport coats – gray and brown are likely your most versatile colors.
If it’s wet out, take a page out of the country gentleman’s book – Barbour waxed jackets or trench coats will keep you dry and your style game on point!
Mix and Match
If by some chance you like multiple aesthetics on this list, then you’re in luck! For the most part, various components of each can be mixed and matched for something uniquely inspired and equally stylish.
The best part of autumn fashion is how it allows a certain level of casual sophistication that’s just harder to pull off in the summer – and women appreciate it a great deal, as well.
It’s a season where dressing well is a heck of a lot easier, and a variety of options and brilliant garments stand to be embraced by you and your wardrobe.