What to Wear in September: 18 Practical Outfits for the Transition to Fall
If you find yourself caught in the constant battle of "Should I wear a coat?" or "Am I still allowed to wear sandals?" this is the perfect solution for you. Here are eleven fall transition clothes that are sure to keep you warm, stylish and free of second thoughts by the time the sun goes down.
Are you prepared to ride the wild ride of September fashion? So, let's go right in.
The Ultimate Casual-Polished Combo You Didn't Know You Needed
You know the vibe: *“I look stylish, but didn’t try too hard.”* That’s exactly what this outfit says.
A structured blazer instantly pulls everything together and gives off that “I’ve got my life together” energy—even if you’re just running out for coffee. Pair it with a graphic tee to keep things relaxed and show a little personality (bonus: they’re super comfy). Then throw on some straight-leg jeans—because let’s be real, they look good on *everyone* and never go out of style.
Want to level it up? Try bold loafers or chunky boots to give it that street-style influencer edge. Just putting it out there.
Timeless Edge: How to Nail the Leather Jacket Look Every Time
There's just something about this outfit—it never fails. It's edgy, timeless, and carries just the right amount of rebellion (even if your wildest act is ordering an oat milk latte).
So, what makes it so iconic? For starters, a leather jacket oozes cool without even trying. Pair it with a classic white tee—arguably the MVP of any wardrobe—and you've already nailed the look.
Then there’s the all-black base. It’s sleek, effortless, and makes room for your accessories to really pop. Want to take it up a notch? Throw on some bold sunglasses or swipe on a red lip. It’s fall, after all—so bring on the drama.
The Ultimate Laid-Back Look: Mixing Classics with a Modern Twist
Cozy Meets Chic: How to Rock an Oversized Sweater with a Midi Skirt
You've probably seen this outfit combo all over the place—and honestly, there's a good reason why. It just works.
What makes it such a go-to fall look? It nails that perfect mix of cozy and chic. Plus, it’s made for layering. When the weather turns crisp, you can easily add tights, boots, or a scarf without messing with the vibe.
It’s also super forgiving—especially if, like me, you treat apple pie as a main food group once October rolls around.
Want to take it up a notch? Try a French tuck (just tuck in the front of the sweater). It adds a little shape at the waist while still keeping that relaxed, effortless feel.
And let’s be real—can you even think of anything more Pinterest-perfect than this look paired with ankle boots and a pumpkin tucked under your arm? Yeah… didn’t think so.
Classic Meets Cool: Styling a Corduroy Blazer with a Mini Skirt and Loafers
There’s something effortlessly charming about the “professor aesthetic”—especially when it’s given a cute twist. It’s the kind of look that’s perfect for the office, a class on campus, or a quick stop at your favorite bookstore (even if you know that novel’s not getting finished anytime soon).
What makes this outfit work so well is the mix of textures and vibes. Corduroy is basically fall’s signature fabric—soft, warm, and full of vintage charm. Pair it with a structured blazer and you’ve instantly taken things up a notch, even if there’s just a basic tee underneath. A mini skirt adds a playful touch, while loafers keep the look clean and put-together.
Want to level it up? Throw on some sheer black tights if the weather’s chilly, and maybe a beret if you’re in a Parisian kind of mood. Let’s be real—you’ll look like you know every indie band on the planet and probably make a mean chai latte, too.
Cool, Comfy, and Functional: Your Go-To Outfit Formula for Busy Days
And finally, we're diving headfirst into full-on comfort-core mode. This look is perfect for those gray, lazy days when all you really want is to stay wrapped up in a blanket—but still look put together.
Here’s why it works: A utility jacket keeps things light but still warm, while a hoodie adds that extra layer of coziness. And leggings? They're the MVP of comfort—no explanation needed.
Want to take it up a notch? Throw on some gold jewelry or a pair of sleek sneakers to keep the look effortlessly cute, not like you totally gave up.
How to Style a Plaid Dress Without Looking Too Sweet
Mixing Comfort and Grace: Oversized Tops + Flowing Skirts Are In
Sounds a little strange? I get it—but hear me out, it totally works. This outfit combo nails that perfect blend of cozy and cute. With an oversized sweatshirt up top and a flowy maxi skirt on the bottom, you’ll feel like you’re lounging in pajamas but still look effortlessly put-together.
What makes it even better? It’s perfect for layering when the weather can’t make up its mind, and it gives off that chill, confident vibe without even trying. Plus, it’s super versatile—pair it with slides, sneakers, or even platform boots, and you’re good to go.
Style tip: Try a French tuck with the sweatshirt. Trust me, it changes everything.
Comfy Meets Cool: Styling Shackets with Biker Shorts and Socks
Yeah, I said biker shorts in a fall outfit—don’t come for me just yet.
Hear me out: this quirky-but-cute combo actually works. The shacket (that perfect hybrid of a shirt and jacket) is a fall staple. It’s warm, oversized, and effortlessly cool—basically made for those in-between weather days. Pair it with biker shorts, and suddenly you’ve got that “just grabbed coffee after Pilates, but also could show up at a street style shoot” kind of energy.
Add some crew socks and chunky sneakers, and boom—you’re giving full-on influencer vibes. It’s ideal for those warmer autumn afternoons when layering still makes sense, but wearing full-on pants feels like too much of a commitment.
Honestly, this look shouldn’t work... but it totally does.
The Classic Combo You Didn't Know You Needed This Season
Turtlenecks might not always get the love they deserve, but come September, they totally shine. There’s just something effortlessly cool about pairing one with a denim skirt and knee-high boots—it’s like you’ve mastered that perfect early fall vibe (even if apple picking isn’t on your calendar).
What makes this combo work? The turtleneck keeps you warm without feeling bulky, the denim skirt brings a laid-back charm, and those knee boots? Pure fall fashion royalty. Want to take it up a notch? Throw on a felt hat or a cute crossbody bag, and you’re good to go.
Mastering Fall Street Style: Cargo Pants, Cropped Knits, and Beanie Vibes
Let’s switch it up for a second—this one’s for the casual girls who live for that effortlessly cool, coffee-in-hand vibe. You know the look. Cargo pants are making a comeback (though honestly, did they ever really go out of style?). Throw on a cropped knit sweater and a beanie, and boom—you’re serving fall street style without even trying.
Think olive green or beige cargo pants, a boxy cropped sweater, and finish it off with chunky sneakers or lug-sole boots. Toss on a small crossbody bag or sling a fanny pack across your chest if you’re feeling it. It’s the kind of outfit that feels like a cozy hug from your stylish older cousin—the one who always looks put-together without breaking a sweat.
Smart, Stylish, and Comfy: Why Button-Ups and Paperbag Pants Just Work
This outfit seriously does it all—perfect for the office, and just as good for the weekend. Honestly, what more could you ask for?
Just roll up the sleeves, tuck in that button-up, and maybe add a pair of gold hoops. Boom—you’re the main character now.
Here’s why it works so well: paperbag pants are insanely comfortable and give you actual breathing room. A crisp button-up instantly pulls the whole look together, giving off that "I’ve got my life together" vibe without even trying. It’s effortless and polished at the same time—a total win.
On a personal note, I basically lived in this outfit last September. No regrets. Not even one.
Chill, Chic, and Ready to Go: Flannel + Faux Leather Vibes
Let’s be real—flannel isn’t just for lumberjacks anymore. When you pair it with black faux leather leggings, you’re basically starring in your own Netflix series set somewhere cozy and dramatic, like Vermont. It’s giving main character energy in the best way.
To avoid looking like you time-traveled from 2012, go for a flannel that’s slightly oversized. Not skin-tight, but not drowning you either—just that perfect in-between. Throw on a simple black or white crop top or tank underneath, and finish the look with chunky sneakers or classic Chelsea boots.
The vibe? “I just split some firewood and whipped up an oat milk latte without breaking a sweat.”
Want to take it up a notch? If your flannel is long enough, belt it at the waist and rock it as a shirt dress. Instant style upgrade, no effort required.
Shacket Season Is Here—and We're Pairing It with Tanks and Bike Shorts
The shacket is definitely still going strong—and honestly, I'm not complaining. It's the perfect piece for those days when it’s chilly in the shade but blazing hot in the sun. You know the type.
Why should you have one in your closet? Because it’s the best of both worlds: part shirt, part jacket—total genius. It keeps your arms warm without making you feel like you’re overheating. Pair it with bike shorts (which, by the way, are comfy, stretchy, and surprisingly stylish), and you’ve got yourself a look that’s equal parts cool and casual.
Want to level it up? Throw on some chunky sneakers and a baseball cap. Just like that, you're nailing the trendy-but-functional vibe.
Fall Fashion’s Favorite Pairing: Cozy Dresses and Killer Boots
This outfit combo totally gets the vibe of fall. There’s just something incredibly satisfying about throwing on a sweater dress and instantly looking put together—like you actually tried, even if you didn’t. It’s the ultimate lazy-girl hack that still turns heads.
Pair it with knee-high or over-the-knee boots, and boom—you’re suddenly the main character in a cozy, leaf-strewn Hallmark movie. It’s effortlessly chic and perfect for everything from brunch dates to coffee runs, or even that random fall wedding you totally forgot about.
What makes this look such a winner? Minimal effort, maximum payoff. It’s a one-and-done outfit that you can easily elevate with a scarf, belt, or a wide-brim hat if you’re feeling a little extra. Want to take it to the next level? Go for a monochrome look. A tan sweater dress with taupe boots? Absolute chef’s kiss.
Street Style Meets Snuggle: Rocking Teddy Coats and Chunky Kicks
Let’s be real—teddy coats are basically like stepping out in your coziest blanket, but make it fashion. And when it comes to fall outerwear, this one’s a total MVP. It’s insanely warm and comfy without sacrificing style, adds instant texture to even the most basic outfit, and somehow manages to go with literally everything—especially your favorite pair of jeans.
Here’s how to style it: Go for a cream or beige teddy coat (bonus if it’s got those oversized buttons), throw on a simple white tee or a fitted turtleneck underneath, and pair it with straight-leg jeans for that effortless, off-duty model vibe. Finish the look with chunky white sneakers or classic ankle boots, and you’re golden.
Oh, and pro tip: this outfit is perfect for travel days. You’ll look totally put-together while feeling like you’re wrapped in a warm cinnamon roll. Total win.
Effortless Style: How to Rock a Denim Jacket and Midi Dress All Year Long
You can’t go wrong with this look—it’s a classic for a reason.
That breezy sundress you’ve been living in all summer? No need to pack it away just yet. Just throw on a denim jacket, and suddenly your outfit is fall-ready without trying too hard. Depending on your vibe, finish it off with some ankle boots for an edgy twist or keep it casual with clean white sneakers.
Here’s why it works: layers make it easy to adjust throughout the day when the weather can’t make up its mind. The dress keeps things feminine and flowy, while the jacket adds a cozy, laid-back feel. And let’s not forget the beauty of a midi length—it saves you from any wardrobe malfunctions on windy days.
Pro tip: cuff the sleeves of your denim jacket for that effortlessly cool, "Oh this old thing? Just threw it on" energy.
The Ultimate Transitional Outfit: Lightweight Sweater Meets Pleated Skirt
Ever wondered how to nail that perfect combo of cozy and stylish in one outfit? This look has you covered.
Start by mixing textures—think a soft knit sweater paired with a flowy pleated skirt. It’s a match made in fashion heaven. You can fully tuck in the sweater for a cleaner silhouette, or go for a relaxed half-tuck if you’re feeling casual—there are no rules here.
What makes this outfit a total win? For one, breathable knits keep you warm without making you overheat. Then there's the pleated skirt, which adds movement and an effortless touch of elegance. The best part? It pairs perfectly with sneakers, boots, or even mules—yep, the ultimate wildcard shoe for early fall.
Pro tip: Try a cropped sweater to really nail the proportions. It’s all about creating balance.
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