20 Ways to Upgrade Your Fall Style for Under $150

If the first hints of fall haven’t reached your zip code yet, they’re well on their way. And let us tell you: It feels incredible. A crisp breeze, a night cool enough to wear a real sweater—this is the season menswear enthusiasts live for. As the instant classic Kermit meme reads: Finally fall, now I can really start dressin’.

Naturally, this means taking a hard look at your rotation. What stays? What goes? What carried you through summer and wants to stick around, and what didn’t see the light of day last fall? Taking this inventory can feel daunting, but here’s the good news: you don’t need to drop racks to get your closet shipshape. Just a handful of affordable, useful pieces will see you through the season and well into winter—and pair beautifully with those soft corduroy pants you invested in last fall. Seriously, there’s no need to toss the core out with the clutter. That’s why we’ve pulled together our favourite fall upgrades, all under $150. Let ’er rip.

The Affordable Fall Upgrade Hit List

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The Collegiate Rugby

If the secret to looking hot this summer was dressing in a striped polo like it was 2005, it stands to reason that this fall, rugby shirts are where it’s at. This slight-oversized one from Kotn—the brand known for making basics way better—was designed in partnership with a heritage Canadian rugby shirt maker, and is as good a take on the style as we’ve seen in years.

The Fall Flannel

Fall = flannel. The preferred shirt texture of cold-weather European and American workers for decades—and then of grunge Gods in the ’90s—it isn’t going anywhere in 2025. Warm, insulating, and easy-wearing, a good flannel like this one pairs with jeans, chinos, a simple tee—basically all the thing you already own.

The Fresh Pack

After a long, sticky summer, we wouldn’t judge if you’ve got a few pairs of underwear that are hanging on for dear life. Now’s the time to retire the holey ones and bring in some breezy boxer shorts. These, in a soft poplin cotton with retro stripes, strike a nice balance of comfort and cool.

The Dark Denim

The season of getting dressed again starts with getting back basics. Therefore: Denim. Forget “added stretch.” Forget avant-garde fits. Don’t even stress about the wash. Dark denim is as simple and good as it gets, and Gap still does it for the right price. This pair comes in a relaxed, straight fit that works with just about everything on this list.

The Soccer Kicks

Helped by the Oasis reunion and the imminent World Cup, soccer style is on the rise. This makes it’s a great time to snag a pair of low-profile, pitch-inspired sneakers, like this under-the-radar pair from Nike. Think gum sole, subtle footy details, and the kind of vibe that says you’ve just trudged off the five-a-side pitch.

The Work Shirt

September isn’t “back-to-school” season for nothing. When it’s time to get back to work for real, let this work jacket spur you on. Made from sturdy cotton and dyed with real indigo, it’s designed to fade and break in beautifully. Essentially, you’ll get out the work you put in.

The Brown Cords

Corduroy pants never seem essential to own… until you’ve owned a pair. A good pair of cords will outlast just about anything else in your closet, and the style’s distinctive soft ridges trap heat way better than denim. Throw ’em on with a knit sweater and some suede boots to discover that texture always triumphs.

The Substantial Socks

Flip-flops and slides were everywhere this summer, so we’ll forgive you if socks weren’t top of mind. But few things feel more autumnal than traditional ragg socks like this, which pair perfectly with hiking boots and chunky sneakers. Trust me: On that first blustery day, you’ll be glad to have a toothy knit pair at the ready.

The Dress Sock

Chunky socks are great and all, but they don’t always go with the workday uniform. For that, we have Todd Snyder’s Italian-made dress socks. The stretchy merino blend feels soft against the skin, holds its shape, and is available in a range of inconspicuous tones to pair well with all the suits in your selection.

The Chunky Slide

When it comes to slip-ons, we of course love the Birkenstock Boston. But so does everyone else! If you’d rather zig while the rest zag, check out the Merrell Wrapt: a grippy, fall-ready slip-on alternative. With its rugged outsole, waterproof pig suede upper, and supportive heel, it’ll get you there—even if ‘there’ is just the corner store.

The Original Fall Jacket

Some things don’t need reinventing, and a Levi’s Trucker Jacket is one of them. A true classic for decades now, it’s the kind of piece that gets better with each transitional season it excels through. The sturdy cotton denim, and signature details make it endlessly versatile, and this relaxed fit model leaves room for any hoodies you want to rock underneath.

The Burrower’s Beanie

In your “honk shoo” era this fall? A good beanie helps you feel like you’re still under blankets, even when you’re miles from home. Even better, when they’re in an offbeat color, they can help flip the script on an otherwise regular-guy fit. Luckily, House of Blanks has 30 shades to choose from, including a Steve Zissou–esque red. Even better, each one is ethically knit, in a family-owned factory.

The Smart Money Puffer Vest

A down vest starts as the only layer you need for fall, then becomes the additional stealth layer you need in winter. Uniqlo’s lightweight, water-repellent, warming PUFFTECH edition does everything you want it to, without hurting your credit score. Use it to get you through fall, past winter, and well into that always tricky stretch of March.

The Cool Quarter-Zip

Much as they’d like to, finance guys don’t get to own the quarter zip. In fact, it can actually be a bit of a style swerve, provided you scoop the right one. This beauty from Massimo Dutti is made from natural fibres (100% merino, check), comes in subdued colors (versatility, check), and is most importantly cut looser with a full collar, for a nonchalant look that’s more Firenze than FiDi.

The Collared Cardigan

A cardigan is of course another classic. And if the flirty crewneck version that dominated your feeds last fall isn’t your style, you’re in luck—this season you can go the opposite route with a collared cardigan. We’ve seen them from the likes of Our Legacy and Mfpen, but as always, Uniqlo has the trend covered for a lot less.

The Slim Belt

There are a lot of belts out there, but Maximum Henry is really making its case for being the only belt designer you need to care about. Even under $150, you’re getting New York-made leather with taste levels that are seriously dialled in. The brand nails the classics, but always tweaks them just enough to keep things interesting.

The Windswept Waffle

Cooler days start with smarter layers. A thin but cozy waffle-knit long sleeve makes the perfect base layer, ready to pair with just about anything: a flannel, a work shirt, even a well-worn chore jacket. But honestly, they can be incredibly sexy on their own—why else do you think Austin Butler wears them so much?

The Workout Top

After a summer of one too many spritzes and “special occasion” meals, a little fresh workout gear might be the inspiration you need to sweat it out. Satisfy’s 100% cotton “MothTech” tees feature strategically placed ventilation (in the form of holes that look like a Moth’s eaten through your tee) and enough style that even if your fitness kick only lasts a few weeks, the top can still earn a spot in your regular rotation.

The Couch-Cozy Sweatpants

Fall also means football season, which means it’s time to get reacquainted with RedZone—in the comfiest sweats you can find. And where fleece-y, comfy sweats are concerned, we’ll always point you towards Champion. If these don’t become the MVP of your fall wardrobe, they’re at least a solid first-round draft pick.

The Workhorse Work Pant

If your denim drawer is full but you still need a pair of all-around pants to cover the utility slot in your weekly lineup, Dickies is never the wrong call. You probably know the classic 874, but the 248 brings that same work-to-street energy with a straighter, looser fit that feels a little less rigid and a lot more relaxed. Not to mention that so-chocolatey-we-could-eat-it color.