Fall Is Coming—18 Transitional Outfit Ideas That Will Make the Shift So Easy


Take note.

Change isn't always easy, especially regarding the shift from summer to fall. As much as shifting into a new season can bring a bevy of things to be excited about, that doesn't mean it won't come with a bit of sorrow. On one hand, we can all collectively look toward the prospect of travel, new trends, and less unbearably hot temperatures. But at the same time, it can mark the end of time away from our desks, sun-filled weekends, and beach getaways. All of this is to say that it can be a bittersweet time, so we all must have our own coping mechanisms to make the transition easier. For me, one of those coping methods comes from spending hours scrolling through social media in search of fall outfit ideas. Like many summer babies, I may be in denial about having to pack away my sundresses, but there's nothing like a few great outfit ideas to break me out of my mood. So in my own self-serving interests (and hopefully for your benefit too), I've rounded up the 18 best transitional outfit ideas. With each ensemble, I've broken down easy outfit formulas and shopped out the key pieces you'll need to re-create them. Plus, I've ensured each includes at least one summer staple that's been styled in a fall-forward way. Whether you're a die-hard summer lover or live for the fall, there's plenty of inspiration ahead that will make the switch easy.

No summer wardrobe is complete without two things: a pair of pleated shorts and minimal mules. If you're not ready to pack them away just yet, make them fall forward by styling them with a turtleneck and trench coat.

Rich energy.

Turtlenecks are a foundational part of every fall wardrobe.

Another simple way to get more usage out of your favorite pair of pleated Bermuda shorts? Pair them with a crew-neck sweater and trend-forward accessories (e.g., sculptural earrings or colorful wedges) for a stunning summer-to-fall look.

Our editors love these earrings.

It doesn't get more timeless than a crew-neck.

For those really warm fall days when you can't possibly get away with layers or sleeves but still want to wear a sweater, let the look above be your blueprint. Pairing a knitted bustier top with shorts (or jeans) and loafers is the perfect way to dress like it's fall, even if the weather forecast isn't there just yet.

Just think of how flattering this will be on you!

Trust me. These are worth the investment.

Skirts are essential to any summer wardrobe, but transitioning them into the fall can feel impossible—until now. Take a cue from the look above and make your favorite pencil, maxi, or any skirt for that matter feel seasonal by pairing it with a leather moto jacket. Depending on the weather, you can finish off the look with mules or boots.

Moto jackets are still cool, FYI.

You can wear this to work or on the weekends.

In addition to skirts, denim shorts are a quintessential part of summer wardrobes. But if you find that you haven't exactly gotten the most wear out of your favorite pair this summer, then make them ideal for transitional weather by styling them with a tank, a cardigan, and ballet flats.

Denim shorts are a year-round thing.

Cool girls, apply here.

Pro tip: The key to mastering transitional dressing is all about making simple swaps. For example, the maxi skirt you've been wearing with sandals all summer? Swap out the shoes for a closed-toe option like ballet flats. Instead of wearing it with a tank, put on a turtleneck for the perfect fall-ready outfit.

Chic, chic, chic.

You can also style this skirt with boots.

Not to sound like a broken record, but just because we're entering the fall doesn't mean you have to stop wearing your favorite summer items. In fact, your beloved slip dress is perfect for transitional weather if you pair it with a leather trench coat and knee-high boots.

Leather trenches are a must-have in my book.

These are the most comfortable heeled boots you'll ever buy.

For those who have been living in ballet flats this summer, the prospect of boot season may not be all that exciting. Luckily for you, there's no shortage of transitional outfit ideas that include ballet flats—ahem, see above! Pair your favorite shoes with fitted jeans and a striped sweater, and you've got the perfect look to wear while drinking a PSL.

Francophiles, this sweater is all you!

Skinny jeans never fully go out of style.

News flash: You don't have to ditch your breezy silk pants for denim if you don't want to yet. In fact, you can make the more effortless silk, satin, and linen trousers in the back of your closet transition into the fall by pairing them with an oversize cardigan and slingback heels.

So cozy.

These are currently at the top of my wish list.

In addition to the breezy pants, the oversize silk button-down is a defining part of the summertime wardrobe. While our inclination may be to pack this piece away, you'll want to think again. You can make a silk or satin button-down feel fall ready by layering it over a T-shirt, under a cardigan, and tucked into a leather skirt.

Are you a stickler for not wearing white after Labor Day? You can also shop this top in four other colors.

A great leather skirt is the backbone of every well-curated fall wardobe.

Ah, miniskirts. While this item may not seem ideal for crisp autumn days, that's far from the truth. Pairing this bottom with fall staples (e.g., a moto jacket and knee-high boots) can seamlessly transition this hot-weather item into colder days.

The semi-distressed look of the faux leather on this jacket is very on-trend.

Don't be afraid to try unconventional color pairings (e.g., mixing brown and black) to add visual intrigue to your fall looks.

An additional way you can transition your miniskirt into autumn is by pairing it with two quintessential staples—a chunky turtleneck sweater and flat knee-high boots. This simple formula will ensure you get the most wear from your miniskirt without being improperly dressed for the season.

Fall embodied in one sweater.

Instead of opting for chunky lug-sole boots this season, go for the more timeless riding-boot silhouette.

Are you not quite ready to give up your breezy linen button-downs in lieu of heavy knits? We get it. Instead of packing them away, pair them with a leather bomber jacket and thick wool skirt for an ensemble that's ideal for the transition into fall.

You'll wear this all the time.

Now here's a skirt that will look good with both boots and sandals.

Prefer slips over any other type of skirt? Well, there's a way you can wear them well into the fall too! Try styling your favorite slip skirt with a striped tee, a blazer, a woven leather bag, and boots for a look that works well no matter how much the temperature fluctuates throughout the day.

Peak fall energy.

Meet your new work-friendly handbag.

If you're ready to start wearing denim again but can only afford to rewear the wide-leg jeans in the back of your closet, there's one outfit formula that you will want to try: a Canadian tuxedo. With double denim trending right now, there's no better time to transition old denim into the fall. However, if you still want to up the cool factor, take a cue from the ensemble above and try cuffing your jeans at the hem to show off your ballet flats, and finish off the look with a trendy studded belt.

Just add your favorite wide-leg jeans!

Studded accessories will continue to be big for the rest of the year, so why not invest?

One of the best things about summer is how effortless getting dressed can be at times. But if you find you're dreading the prospect of having to squeeze back into jeans again, there's an alternative bottom that works well for the transition from summer to fall, stirrup leggings. Style them with an oversize button-down, a blazer, and loafers for a look that's both cozy and chic.

Madewell's blazers never disappoint.

Make these leggings feel more stylish by wrapping the strap around the outside of your shoes.

We all have that perfect white T-shirt we lived in throughout the summer. But rather than packing it away, why not try pairing it with other beloved fall staples? Rest assured, you'll love how your favorite tee looks with colorful leather trousers and ankle boots—it's a foolproof formula.

In case you're ready to upgrade your T-shirt.

Olive-green leather for fall? Spot-on.

Hopefully, by now, you've got a few ideas of how to transition some of your favorite summer items into the fall. But should you need one last nugget of parting wisdom, let it be the following: When in doubt, layer in fall items. The easiest way to make even the most casual summer items transition into the fall is by adding those peak-fall pieces to your look. For example, the tank top and jeans you've been living in all summer can feel fall forward when styled with a tweed jacket and ballet flats. Anything can be fall ready. You just have to be willing to take the summer items you love and get creative with your styling.

The buttons on this jacket add a touch of elegance.

Tory Burch does it again.

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