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11 wardrobe essentials every woman needs to transition from summer to fall

These are the expert-approved pieces you need in your closet for the upcoming season.
Two booties and a sweater
Kara Birnbaum / TODAY / Vivian Le / TODAY
/ Source: TODAY

We love summer and fall, but that tricky transition period in between the two seasons can cause quite a few style conundrums. When the weather is warm one day and chilly the next, figuring out what to wear can be challenging at best, and completely frustrating at worst.

To help you fashionably navigate this confusing in-between period, we sought the help of top fashion stylists to curate a list of the essential summer to fall wardrobe pieces you need. We also asked them for some money-saving tips to help you stick to your budget!

How to save while shopping for transitional pieces

Want to be kinder to your wallet as the seasons change? There are ways to shop your own closet if you’re not up for a full-on wardrobe refresh. Here are a few pro-approved tips to get you started:

  • Look before you shop: “Delve into your own wardrobe first to see what trends you may already own and refresh your memory on some of those items that are way in the back of your closet,” celebrity wardrobe stylist Audrey Brianne said.
  • Consider how long you’ll wear something before you buy it: “Step one is making sure you shop with purpose, duality and keeping in mind how clothes will keep up day to day with an on-the-go lifestyle. Durability is a huge part of transitioning your seasonal wardrobe,” Brianne advised.
  • Don’t forget about thrift shopping: “Look into secondhand shopping platforms to score pre-worn pieces and save money,” Rakuten Retail & Shopping Expert Kristen Gall said.

Stylist-approved transitional clothing pieces from summer to fall

White jeans

Who says you can't wear white after Labor Day? This wardrobe basic can easily transition into the fall season. "Simply swap out your breezy summer tops and pair your denim with cozy knitwear and a scarf," said Dana Asher Levine, Hollywood stylist and DHStyle Inc. CEO.

Venus Bootcut Jeans

Asher Levine suggests easing into fall with a cropped pair of white jeans that's perfect for those steamy, early fall days.

Riders by Lee Indigo Women's Fringe Cuff Boyfriend Jean

The best part about a crisp pair of white jeans? You can pair them with a range of footwear options, including flats, booties or heels!

Button-up blouse

Since they're not too heavy (like a sweater) and not too light (like a sleeveless top), long-sleeved blouses are a pretty great transition piece. "A crisp white men’s style shirt can be dressed up or down and layered under a jacket if it's cool outside or worn on its own if it’s still warm enough," said Natalie Bronfman, costume designer for Hulu's "The Handmaid's Tale." The same goes for chic silk blouses!

Old Navy Oversized Boyfriend Long-Sleeve Shirt

A crisp, oversized white blouse is a style staple that pairs equally well with a pencil skirt and tights or jeans and flats so you can get a lot of mileage out of it.

Banana Republic Factory Satin Classic Shirt

Sometimes, all you need is a bit of texture to make a style statement during that awkward transition phase. This trendy silk blouse comes in six colors, including neutrals and some gorgeous jewel tones, and is made of a stretchy material that promotes comfort.

Basic pullover sweater

When the air gets a little chilly, reach for this versatile wardrobe essential. "Whether needed on a brisk summer night watching fireworks or layered over a favorite button-up in the fall, this trusty piece is easy to wear year-round and won’t steer you wrong," Brianne said.

Croft & Barrow® Striped Crewneck Pullover Sweater

Not ready to give up the soft, sweet colors of summer? This cozy crew neck sweater comes in four pretty pastel hues that will help you hold onto that carefree summer vibe even when the temperature drops.

Belldini Puff Shoulder Heart Sweater

Depending on where you live, the early days of fall can still be quite warm. If a long sleeve pullover is too heavy for the moment, a short-sleeved sweater like this heart print style is a great alternative.


If you’re on the hunt for a wardrobe staple you can wear all year long, consider your quest complete. “Cardigans help with chilly nights during the summer and can easily be layered under or over tops in fall for a bit of flare,” Brianne said.

Lands' End Cotton Modal Open Drape Cardigan

Looking for a new sweater to keep you warm at the office while the air conditioner is still blasting? We’re digging this draped style that’s made of a material that resists pilling.

Coolibar Marietas Sun Wrap UPF 50+

We’re suckers for multitasking clothing that serves multiple purposes, like this UPF 50+ sweater that doubles as a cardigan while it protects your skin from the sun. The lightweight, flowing style is available in nine sizes and 10 colors!

Midi or maxi dresses and skirts

Those easy, breezy long dresses and skirts you rocked all summer will come in quite handy when the temperature drops. And creating a fall-ready look with a midi or maxi dress/skirt is easier than you may think.

“Paired with a bodysuit, tank or crop top, maxi skirts are perfect for warm weather. Easily mix them with a sweater, turtleneck and high socks for winter and it’s a seamless transition using items that are most likely already in your closet,” Brianne said.

Gap Puff Sleeve Sweetheart Midi Dress

Opt for a lightweight midi dress in a fall color and layer it with a jacket, neck scarf and belt for a topnotch transitional look. This versatile style would work equally well at work, home and during a date night, and has fun puffy sleeves and a romantic sweetheart neckline.

Loft Heart Bias Midi Skirt

For the perfect fall look, Asher Levine recommends rocking a printed midi dress or skirt — like this vibrant green heart print — paired with fancy boots or booties. We dig the sassy side slit and flowy silhouette, and also appreciate that it has a comfy elastic waist.


Blazers aren't just for the boardroom! A fun style in a bold color can help you transition through all four seasons, but is especially ideal for that short period between summer and fall. "A beautifully tailored blazer is perfect for the fluctuating temperatures and can be worn on its own or under a trench," Bronfman said.

Eimin Lightweight 3/4 Sleeve Blazer

Jill M. Ohanneson, costume designer for AMC's "Preacher" and ABC's "Revenge," recommends trying a lightweight blazer in a plaid or rich jewel tone to pair with your summer jeans.

HyBrid and Company Blazer

Fashion stylist Catherine Schuller suggests opting for a blazer with a touch of stretch so you can wear it over blouses, tank tops or even long-sleeved shirts.

Trench coat

“A statement trench coat in mouth-watering plum, classic navy, charcoal black or faux leather is a wardrobe must for fall. It gives you practical coverage, while keeping your outfit sleek and sexy,” celebrity fashion stylist Cindy Conroy told us.

Sebby Water-Resistant Hooded Double-Breasted Trench Coat

Early fall weather can be a bit unpredictable, so keeping a wind- and water-resistant jacket in your closet is always a smart style move. This one comes in several neutral and statement colors and even has a removable hood!

“Once the weather starts to get cooler, you will want to pull your jackets out from storage, as well as likely invest in a new one for the season ahead. It is important to have a few different jackets if possible, depending on the weather,” Gall said.

New York & Company Ruffle Trim City Trench Coat

Sick of the same old trench coat year after year? Switch things up with a gorgeous blue hue. This affordable find has clean lines, a flirty ruffle trim and a sleek belt. It's ideal for layering on top of sweaters and also comes in two other neutral colors!

Stylist-approved transitional accessories from summer to fall


This style staple is perfect for multiple seasons and is the ideal piece to kick off fall. "Booties are a year-round staple. Fashion rules like 'no white after Labor Day' and 'boots only in the winter' don’t exist anymore. The new fashion generation has changed all the rules for the better," Asher Levine said.

LC Lauren Conrad Curve Top Western Boots

Knee-high boots and booties are a staple paradise, but have you tried cowboy boots? One of the season’s biggest trends and oh-so delicious, short and tall cowboy boots pair perfectly with breezy summer dresses and shorts,” Conroy said. This pretty pair is a subtle way to wade into the trend and the price is certainly right.

Blowfish Malibu Sonny

The best part about booties? They can be dressed up or dressed down, so they're the perfect investment piece. We’re particularly fond of this pair’s ankle buttons and love that the style comes in multiple textures!


We never really need an excuse to wear this classic shoe style, but they're especially useful this time of year. "Flats can help you transition seamlessly to fall and get you out of your easy-breezy sandals," said Hollywood costume designer and private stylist Leesa Evans.

A New Day Meredith Ballet Flats

A classic pair of black or brown flats is perfect year-round and can help you tie any ensemble together. This affordable pair has a stretchy back that makes it easy to slip in and out of and an equally appealing subtle sheen.

Native Shoes Audrey Print Flat

Available in two polka dot patterns, this slip-on style is perfect for the gal on the move who doesn’t have time to fuss with laces. As an added bonus, it’s made of a handy bacteria-inhibiting material.

Textured accessories

“Experiment with texture from head to toe. Nothing spells fall like a shearling bag or suede belt,” Conroy told us.

Genuine Suede Square Buckle Belt

This snazzy suede belt is a total bargain, yet it’s anything but cheap. The versatile style can elevate jeans and a white blouse or tone down a dressy look, making it a multitasking accessory that’s worth adding to your ever-growing collection.

Ann Taylor Plaid Knotted Headband

Plaid is always one of our go-to patterns for the early days of fall and this headband is an easy way to dip your toe into the trend without fully committing. The budget-friendly find has notes of orange, blue, purple and white, which combine to form a fall-ready print.

Leather crossbody bag

Making the transition between seasons can be as simple as wearing an anchor piece like a crossbody bag to tie together different color schemes. "It’s a perfect day-to-night accessory 365 days of the year. Opt for dark colors like black, brown or navy because they’ll complement any outfit," Brianne said.

Sonoma Goods For Life® Barlow Crossbody Bag

A mini bag in a neutral color can help you go from festival season to breezy autumn days with ease. Available in five shades, this breezy bag features adjustable straps and several pockets so you can store all your essentials.

Madewell The Simple Leather Crossbody

We can definitely see why this thin crossbody bag is a must-have for fall! The versatile style features an adjustable strap and is made from vegetable-tanned leather that handles wear and tear like a champ.