10 Early Fall Outfit Ideas for Transitional Seasonal Style

Summer Fridays and pool days may be in the rearview mirror (sorry, we don’t make the rules!), but here’s the good thing about September: You needn’t stow away your beloved warm-weather looks just yet. Sure, you likely won’t be strolling around in a one-piece swimsuit anymore, but your tanks and Bermuda shorts? Those are fair game. The key to conquering early fall style is experimenting with transitional outfits, which means pairing lightweight styles with your favorite autumnal pieces—think, for instance, a sleeveless knit top with a denim midi skirt and leather knee-high boots. Learning the art of layering is beneficial, too: We love tossing a cardigan over our shoulders for a bit of extra warmth, and wearing a midi dress atop wide-leg jeans is another intriguing styling hack to tap into. Eager for more ideas? Read on for 10 summer-to-fall transitional outfit ideas ahead, complete with accompanying pieces to shop the looks while you’re at it.

Office Bound

Spending time in the office as fall’s organized energy gets into full swing? If so, you’ll need a chic blazer to see you through work days. Pair it with tailored trousers, a knee-length skirt, or even a minidress, depending on your office dress code and overall taste. Round out the 9-to-5-approved ensemble with leather knee-high boots—it’s not too early to take them for a spin. If the AC is always on full blast, an oversized scarf can moonlight as a blanket.

Put It in Neutral

If you’re a bona fide minimalist, you likely don’t stray too far from your go-to neutral color palette—and hey, that’s OK! For the base of your look, consider a white denim maxi skirt with a dramatic front slit: This is sure to stand out against a fitted basic black tee. From there, tie everything together with sleek black accents, such as an understated shoulder bag, chunky belt, and knee-high boots.

Beyond Bold

Bold dressers will surely love Kylie Jenner’s eye-catching outfit here. Follow her lead and team your summery floral skirt with a cozy, of-the-moment butter yellow cardigan. Then, ground the striking patterns and bright hues with a neutral tee or bandeau top. As for footwear, the beauty mogul went with strappy sandals, but ballet flats are a great alternative if heels aren’t your thing.

Proportion Play

No need to bid farewell to your quirky cropped graphic tanks—simply style them with high-rise jeans or trousers and a little red shoe for a seasonally appropriate rendition for the fickle weather. If you’re worried about the temps dropping later in the day, throw a light knit in your bag (you’ll thank us for this tip later).

Effortless Adventures

Everyone needs a foolproof weekend outfit on standby because you never know what a Saturday afternoon has in store—and it seems Amrit found the perfect formula. Above, the DJ and fashion girl rocks a denim button-down and slouchy black trousers. (Wearing a short-sleeve top underneath is a sound idea if it’s balmy out.) Her accessories—sporty sneakers, an oversized tote, and an olive green baseball cap—add a practical element to the outfit. Should you want to jazz up the look, a statement necklace will do the trick.

Pretty in Pink

Rosettes had a moment in the sun this summer—and who says you can’t transition the sweet detail into fall? As exhibited above, the trend (especially in pink) looks great juxtaposed with classic high-rise denim, an autumn-ready silhouette. Play up the ladylike vibes by accenting the outfit with a slouchy bag and pointy heels in various pink shades.

Hit the Town

When it comes to sultry evening-out style, Lori Harvey has it on lock. Case in point? This chic leather trench coat and gray mini dress duo. As shown here, tights are an excellent addition to the outfit once chilly weather rears its head. Emulate this look for your next Friday night outing, whether the evening entails espresso martinis with friends or a dinner date.

Cardi Party

Another layering idea: Sport your favorite cardigan—bonus points if it’s bright and cheery—over a gauzy midi dress. This combo works for various occasions, from a low-key weekend brunch to a day at the office (just add loafers). Keep the cozy yet elegant vibes going with calf-length socks in the same color palette.

Back to Basics

Nothing screams fall quite like a khaki trench coat. Thanks to its billowy, puffy sleeves and cropped silhouette, this iteration is a real compliment magnet. Before going into full autumn mode, pair the timeless jacket with short shorts for a summery spin. Finally, white sneakers will steer the outfit in a casual direction.

Next-Level Layering

Here, we encounter the aforementioned dress-over-pants look. Content creator Tatenda Luna showed us a fresh way to test drive the trend: Layer a flowy, floor-sweeping buttoned dress over relaxed denim. Because no outfit is complete without cute accessories, the influencer sprinkled in dainty gold necklaces and cherry red pieces, including a pocket-heavy carryall and round-toe ballet flats. In our book, this is the perfect transitional outfit.