30 Perfect Outfits to Wear While Transitioning Into Fall

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Summer-to-Fall Transitional Outfits | STYLECASTER
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Labor Day may be over, and with it the endless-seeming summer days, but that doesn’t mean we’re quite ready to swaddle ourselves in 20 layers of cashmere, wool, and leather, either. (And with a forecast in the sunny 70s for New York Fashion Week, clearly we don’t need to yet.)

Still—we’re also getting excited for fall trends and the end of hair-ruining heat and humidity. So, how do you dress for that awkward transitional season, when jean shorts and white sundresses no longer cut it, but autumn hasn’t quite arrived?

MORE: 30 Gorgeous Fall Hairstyles to Try Now

For the next few weeks, while we all patiently sip our basic-but-delicious PSLs and wait for true fall to arrive, dressing can be difficult. Don’t get ahead of yourself and pack away your summer dresses and minis just yet, because we’re here to help you embrace this-so-called fifth season. The key to dressing for transitional weather is to mix your summer pieces with a few of your classic fall items, like a lightweight turtleneck, blanket scarf, booties and jacket.

MORE: 25 Pairs of Fall Boots to Shop ASAP

Ahead, check out 30 outfits and styling tips that will help you feel ready (or at least readier) to embrace fall.

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STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Chic Sneaks

Sneakers and dark denim look cool any time of year—and a wool overcoat in a bright hue like this one is one of the easiest (read: laziest) ways to make a chill summer outfit work when it gets chilly.

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Summer Skirt + Fall Accessories

Layer a chunky knit sweater over your summer midi skirt and add a scarf and sneakers (or heels).

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Bare Legs + Boots

Can't let go of your shorts just yet? Don't worry, just layer on a turtleneck, utility jacket and boots for a faux-fall look.

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STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Suit Up

Power suits are trending this fall, so make yours an office favorite this season by layering on a colorful faux fur stole and color block heels.

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Just a Bit Bundled

Pair your mini with a cropped jacket and draped blanket scarf for an effortless look this fall.

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Black + Brights

It's officially acceptable to break out your beloved black turtleneck again. Pair it with your favorite summer blazer, trousers, and ankle boots. The pop of color makes this look ideal for baby-stepping into fall.

Photo: Getty Images
Photo: Getty Images
Oversized Layers

The easiest way to transition your summer tee and jeans to fall is by pairing them with an oversized cardigan, kimono or poncho. Complete the look with boots and a little neck scarf.

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Trench Tips

Update your casual weekend tee and jeans with a checkered trench and booties.

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STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Office-Ready

Hello, yellow! Match a vibrant long-sleeve sweater with your favorite summer skirt for an easy transitional office look.

Photo: Beauticurve
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Seasonal Sets

Not sure what to wear for this in-between weather? Modify your matching summer set or jumpsuit by layering on monochromatic accessories and outerwear. You can also put on a lightweight shirt or turtleneck underneath the set on colder fall days.

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Cozy Touches

Transition your favorite office pencil skirt from summer to fall by adding knee-high boots and a shearling collared jacket.

 

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Legs For Days

Take your mini from summer to fall by adding a cool combat boot and chunky waist belt. Finish off the look with a bomber or leather jacket and metallic accessories.

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Light Denim + Dark Separates

For this off-duty look, match a classic crewneck sweatshirt with light-wash denim, an oversized coat or trench, and boots.

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Layer, Layer, Layer

Wrap a lightweight sweater around your mini and drape a utility jacket over your shoulders. No matter what the weather might be, you'll be prepared with a couple extra layers.

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Fresh Crop

Create an updated version of the monochromatic power suit this season with cropped trousers and a matching trench coat. Keep the look simple with a tee and pointed pump.

Photo: GabiFresh
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Ready to Cargo

Forget what you know about cargo shorts—because cargo pants are the perfect pant for fall! Roll them up a couple times to show off your boots, leave your blouse untucked, and finish the look with a leather jacket.

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Sporty + Formal

Mixing athleisure pieces—like these tracksuit-inspired pants—with fancier, more ladylike accessories, like pumps and a fur vest, reads as breezy yet substantial enough for a brisk day.

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STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Canadian Tux FTW

Elevate your Candian Tuxedo for fall by adding a printed peacoat and dark bag.

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Print Pro

Print mix your way into fall by pairing a graphic tee, patterned coat and scarf together. The key to mixing various prints in one cohesive look, is by sticking to one or two color schemes.

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Sheer Gorgeous

Layer your sheer summer dress over a black slip, and add a leather jacket to make your favorite piece last another season.

Photo: Nicolette Mason
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Fall on Top, Summer on Bottom

Offset a layered oxford and sweater with a leather mini and sneakers. By breaking up the top layers with a mini skirt, the overall outfit is the perfect match for transitional weather.

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Cap It Off

Oversized sweaters and felt hats in dark shades are a couple of the simplest ways to make any outfit feel cozy and fall-appropriate.

Photo: Getty Images
Photo: Getty Images

You won't have to say goodbye to your crop top for fall because, you can layer it on top of a thin turtleneck or blouse. Complete the look by adding a leather jacket or blazer on top.

Photo: Getty Images
Photo: Getty Images
Fall Dress Done Right

Take your summer dress into fall with you by layering a long sleeve underneath, or adding a chunky knit on top.

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STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
That's Bomb

Elevate your jumpsuit game for fall by adding a bomber jacket and sneaker.

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Get Creative With Cropped Jeans

Cropped jeans have dominated the fashion scene this year, so to keep them fresh for fall, add a chelsea boot, cropped jacket and an oversized blanket scarf.

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Done and Dusted

Pair your summer tunic dress with a lightweight duster jacket and suede booties for fall. Also, you can easily define your waist and break up the long layers with a wide belt or crop top.

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Menswear-Inspired

Say goodbye to work-appropriate ballet flats and stilettos; instead, pair your suit with platform boots and an oversized button-up shirt this season.

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STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
All-Purpose Skinny Jeans

Black skinny jeans can be paired with still-summery open-toed heels and a light-hued leather jacket for warmth (without going into full-0n freezing weather mode).

Photo: Getty Images
STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
Shades of Gray, Navy, and Black

Everything's on point about this look, from the metallic pewter midi skirt to the patent-leather oxfords.

Photo: Getty Images

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  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • Photo: Getty Images
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • Photo: Getty Images
  • Photo: Getty Images
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas
  • STYLECASTER | 30 Summer-to-Fall Outfit Transition Ideas

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