The period between summer and fall is a confusing one when it comes to what is weather-appropriate attire. Some days have an extra-chilly breeze, and others seem to feel like the first day of summer all over again.
Thus, figuring out what to wear can be challenging at best (and completely frustrating at worst). Can maxi skirts work with booties as they do sandals? Should we start swapping our tees for sweaters? It's a tricky answer for even us to answer, which is why we sought the help of top fashion stylists.
Our experts curated a list of the essential summer-to-fall wardrobe pieces you need, along with their top picks and trend predictions for the upcoming season. We even included some of our favorite fall fashion essentials to help you fashionably navigate this confusing in-between period.
Keep reading for the best transitional clothing items and accessories, according to experts and editors.
What's the best way to layer transitional fall clothing? | Stylist-recommended clothing | Stylist-recommended accessories | Editor-loved fall essentials | How we chose | Meet the expert
What's the best way to layer transitional fall clothing?
Clothes shopping at the beginning of fall can be complicated, but it doesn’t have to be. According to Rivera, there’s a "three layer rule" her team likes to follow for this in-between season. You’ll first want to start with a lightweight base layer, following with a versatile middle layer, “like a plaid shirt, cozy cardigan, or a preppy blazer,” she adds.
You’ll then top the layers off with an outer layer “that offers both protection and personality, like a rugged denim jacket or a puffer jacket in a silver hue.” Following this rule should help you balance what’s trendy with functional pieces.
Best stylist-recommended transitional clothing
Tailored blazers
Stitch Fix stylist Alex Rivera has this at the top of her list, suggesting that blazers are “easy to layer over summer dresses or tees to prepare for unexpected brisk weather.” Costume designer Natalie Bronfman also previously told us that blazers "can be worn on its own or under a trench” for extra coverage.
To enhance the waist: Fore Fitted Blazer
- Slimming silhouette
- True to size
Shade range: 1 | Size range: XS to XL | Material: Polyester
Oversized silhouettes might be in, but add some variety to your blazer collection with a fitted one. Stylist Melissa Chataigne specifically recommends this find from Fore, which has a more fitted waist and sleeves to hug all the right places. While we love blazers for layering, we could see this pick being worn on its own.
Not all blazers are perfect in size, though, so Chataigne shares a piece of advice on where you should spend your dough: "It does not matter where you purchase your blazer; definitely spend $20-50 more for tailoring," Chataigne says. "It will look better and you’ll feel more confident."
If you prefer more room to layer: Zara Oversized Double Breasted Blazer
- Structured and oversized
- Can be too long
Shade range: 3 | Size range: XS to XL | Material: Polyester, viscose and elastane
Recommended by wardrobe stylist Tracy Shapoff in our best blazers coverage, this has all the right details for fall: An oversized design that might aid with layering, extra padded shoulder pads and a length that hits below the hip. "[It] seems to have a great balance for most body types," she noted.
Denim or leather jackets
“In just the last three months, we’ve seen client requests for denim jackets spike 11%,” Rivera says. Denim jackets add a casual and rustic charm to your outfit while being a lightweight outerwear option. Christina Stein, a personal stylist, also suggests playing with leather jackets, which might offer some dimension.
A true fall layer: Quince 100% Organic Cotton Oversized Denim Jacket
- 100% cotton
- Oversized design
- Some say it runs large
Shade range: 7 | Size range: XS to XL | Material: Cotton
You can't have fall without a denim jacket, so it is no wondering search for the style has gone up. But we're not just referring to any denim jacket — we're talking about an oversized denim jacket, such as this pick from Quince. "The loser silhouette is elevated," suggests Chataigne, plus, great for layering over and underneath, too.
An effortless style: Levi's Lelou Shrunken Moto Jacket
- Slim and cropped
- Asymmetrical zipper
- Do not wash or tumble dry
Shade range: 2 | Size range: XS to XL | Material: Polyurethane
Recommended by stylist Christina Stein, Levi's Lelou Moto Jacket is effortlessly cool, just like you. With its cropped design, asymmetric zipper and slim cut, everyone will be asking all about it (and you!).
Skorts or tennis skirts
Sporty-chic, anyone? Sporty attire isn’t just a trend — these pieces (i.e. tennis skorts, leggings) are practical for layering “with colored rugby shirts, oversized sweaters and zip-up jackets,” recommends Rivera.
A brand with an impressive size range: Girlfriend Collective Skyline Sport Skort
- Goes up to a 6XL
- Great for curvy bodies
- Eco-friendly fabric
- Price is on the higher end
Shade range: 13 | Size range: XXS to 6XL | Material: Recycled water bottles and spandex
Chataigne couldn't boast more about Girlfriend Collective, especially their Skyline Sport Skort, mainly for their extended sizing that accommodates to body types up to a size 6XL. Plus, “[It’s] made out of recycled water bottles, offers a four-way stretch, [is moisture] wicking and can be styled from day to night," she adds.
Layering pieces
Light knits, cardigans, dresses, long-sleeve tees, just to name a few, are essential for adapting to fluctuating fall temperatures,” says Rivera. “Plus, they can be mixed and matched with all your autumn essentials.”
For light layering: Old Navy Shaker-Stitch Cardigan
- Multiple lengths available
- Inclusive sizing
- Cozy fabric
- Hits at the hip
Shade range: 7 | Size range: XS to 4X | Material: Polyester and cotton
“Cardigans help with chilly nights during the summer and can easily be layered under or over tops in fall for a bit of flare,” celebrity wardrobe stylist Audrey Brianne mentions. Brianne didn't suggest this pick, but the loose fit and cozy fabric are similar to her styling suggestions.
Just as cozy as it looks: & Other Stories Alpaca-Blend Knit Sweater
- Alpaca and wool blend
- Relaxed fit
- Few sizes
Shade range: 4 | Size range: XS to L | Material: Alpaca, wool, polyamide and spandex
“Simply swap out your breezy summer tops and pair your denim with cozy knitwear and a scarf,” said stylist and DHStyle Inc. CEO Dana Asher Levine, who previously spoke to TODAY. We based this pick off her suggestion, which contains an alpaca-wool blend that is just as warm and fuzzy as it sounds. Since it has a relaxed silhouette, it is lightly draped around the shoulders and chest without looking boxy.
A classic button-up: Madewell Alexa Chung Pleat-Pocket Button-Up Shirt
- Perfectly tailored
- Pockets
- Runs a bit big
Shade range: 1 | Size range: XS to XL | Material: Naia acetate
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, such as this one from Madewell. “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 Bronfman. While this was not picked by the stylist, we selected it based on her suggestions.
For a bit of flare: Asos Edition Raw Edge Ruffle Maxi Dress
- Tie-back fastening
- Drawstring waist
- Might be long on some
Shade range: 3 | Size range: 0 to 14 | Material: Chiffon, polyester
Before you ditch your dresses, take a peek at this chiffon maxi dress from Asos to pair with your fall attire. “This is the perfect flowy dress to transition to fall and mix it up with statement suede boots,” suggests Chataigne.
Midi and maxi skirts
“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 previously mentioned to us. We love them for summer, and love them ever more for fall.
A trend we'll never get over: H&M Denim Maxi Skirt
- Multiple washes
- Split hem
- Might be too long on some
Shade range: 3 | Size range: XXS to XXL | Material: Polyester and cotton
You might have mixed opinions on maxi skirts, especially denim, but they are more versatile than one might think. “Paired with a bodysuit, tank or crop top, maxi skirts are perfect for warm weather," Brianne previously said. Although this wasn’t picked by Brianne, this style is most similar to her suggestion.
Most versatile: J.Crew Gwyneth Slip Skirt
- Tall sizing available
- Elastic waistband
- Some say fabric is thin
Shade range: 6 | Size range: XXS to 3X; tall available | Material: Polyester
"I love combining a midi skirt with a motorcycle boot for an edge," recommends Chataigne, which shows just how versatile a slip skirt can be. Wear it with heels, flat, boots and any other style you have in your closet — this style goes with it all.
Trench coats
You can never go wrong with a trench coat for fall. Not only are they stylish, some have practical features for unpredictable weather (such as a water-resistant outers). That’s why Chataigne recommends adding the style to your rotation.
An affordable trench: Gap Factory Modern Trench Coat
- Removable tie belt
- Classic design
- Might be long on some
Shade range: 2 | Size range: XS to XXL | Material: Cotton
Chataigne says this Gap trench is "a no-brainer investment to style all year around," and we couldn't agree more. From its entirely cotton-made construction to lapel details, the trench is a true classic.
To prep for winter: Jason Maxwell Long Coat with Tie Belt
- Great to bring into winter
- Removable waist belt
- No buttons
Shade range: 4 | Size range: S to 3X | Material: Polyester, viscose, acrylic, nylon and cotton
Just looking at this trench-inspired coat tells us that it will keep you warm on those brisk fall days. Better yet, it could even be a good transitional piece into the winter. Chataigne especially loves it in the butter suede color, but there are three other colors to choose from.
For rainy fall days: Aritzia Babaton Torrent Trench Coat
- Lightweight
- Water-repellant
- True to size
Shade range: 3 | Size range: XXS to XXL | Material: Polyester and cotton
A trench coat is one of the most versatile ways to level up your fall wardrobe, and it happens to be one of the most useful. For instance, this Aritzia trench (which we based on expert advice) has a trendy relaxed build and water-repellent fabric that makes it equally stylish and practical for rainy days. “It [trench coats] gives you practical coverage, while keeping your outfit sleek and sexy,” celebrity fashion stylist Cindy Conroy previously told us.
Best stylist-recommended transitional accessories
Ballet flats
We’ve seen ballet flats reign every single season, and have seen a search increase since Sept. 2023. “These shoes work with multiple trends and are comfortable for changing temperatures since they can look great with a sock,” suggests Rivera.
To add a bit of variety: DV Dolce Vita Maysa Ballet Flat
- Elasticized straps
- Faux leather
- No wide sizing
Shade range: 4 | Size range: 5 to 12 | Material: Faux leather
"Silver ballet flats are perfect for those who may be intimidated by styling metallic clothing!," Rivera says. "These are perfect for adding a touch of fun to your everyday wardrobe and pair great with a variety of colors and patterns."
A bestselling flat: Madewell The Greta Ballet Flat
- Luxury leather
- Comfortable
- Wide not available
Shade range: 13 | Size range: 5 to 12 | Material: Leather
“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. Although Evans didn't suggest this pick, these Madewell flats are top-rated (and a bestseller!) for their versatility and comfort for every day of the year.
Leopard print
Animal print is taking over fall, especially leopard. Go bold with leopard by implementing it through your layering pieces, or stick with added it as a pop of print through your accessories.
Dive into the leopard trend: DV Dolce Vita Voyage Sneaker in Leopard
- Cushioned insole
- Trendy design
- No wide options
Shade range: 3 | Size range: 6 to 11 | Material: Faux leather and fabric
If you're intimidated by wearing leopard print in your clothing, Stein recommends showcasing it in your accessories instead. "A fun leopard print sneaker is an easy way to try the trend without a full on commitment," she says, such as the pick above.
Red pieces
If you're shopping for any color this fall, we recommend not sticking to neutrals — and our experts agree. Red will be one of the most loved colors this fall, and it happens to work for every season. Wear it as a pop of color, in a monochromatic look, your makeup and whatever else you imagine.
Keep it subtle: JW Pei Harlee Shoulder Bag
- Water-repellant
- Large compartment
- Fits iPhone 15 Pro Max & below
Shade range: 10 | Size range: 11.02” x 4.33” x 1.65” | Material: Faux leather
Although there are nine other colors available in this style, Chataigne has her eyes on the warm burgundy. Unlike other shades of red for fall, this hue is warmer and toned down for just a teeny bit out of your comfort zone. "Add this gorgeous Pei Wei Wine Colored [bag] with all your outfits this fall, and it works well from day to night," she adds.
Heels with comfort: Aldo Lennoxie Slingback Heels
- Kitten heel
- Padded insoles
- Closed-toe
- Might be narrow for some
Shade range: 1 | Size range: 5 to 11 | Material: Synthetic, patent and rubber
If you haven't tried Aldo's Pillow Walk line, now is your sign to. Not only are these slingbacks, recommended by Stein, just a bit above an inch, they also have padded insoles for all-around comfort.
Motorcycle boots
Chataigne recommended moto boots in our previous coverage on fall boots — and she suggests them again for transitional attire. Most have a chunky, thick sole and a below-the-knee height for comfort.
If you prefer a lower boot: Steve Madden Brycin Moto Bootie
- Great heel height
- Eye-catching details
- Runs a bit narrow
Shade range: 1 | Size range: 6 to 11 | Material: Leather
Steve Madden boots on sale? Sign us up. If you prefer a lower heel and height, these booties, recommended by Stein, are just above an inch and a half, and hit right above the ankle.
An edgy boot: Crown Vintage Reny Boot
- Comfortable
- Eye-catching details
- A bit heavy to wear
Shade range: 1 | Size: 6 to 11 | Material: Leather
Now that motorcycle boots are in, Chataigne loves the simplicity and edge these Crown Vintage boots offer, including the tasteful ankle buckle.
Textured accessories
Add some dimension to your wardrobe with textured details. Instead of sticking with solid colors and textures, our experts love experimenting with pebbled leather, braided bags and more for fall.
All about the details: Anthropologie The Kalani Woven Knot Clutch
- Can be worn as a crossbody
- Comes in multiple colors
- Made from faux leather
Shade range: 7 | Size: 7” x 10” x 0.5” | Material: Polyurethane; polyester lining
“Experiment with texture from head to toe [when it comes to accessories],” Conroy previously told us. And we instantly look to braided details like the ones on Anthropologie's The Kalani Woven Clutch (not picked by Conroy; selected based on her suggestions), which makes it a statement piece on its own.
Braided textures are also versatile for both summer and fall, so you can bring this clutch day-to-night regardless of the season.
Best editor-loved fall fashion essentials
Go mini: Old Navy Utility Mini Skirt
- Available up to a size 30
- Affordable for quality
- Runs slightly small; size up
Shade range: 3 | Size range: 0 to 30 | Material: Cotton
"One of the pieces I have my eye on this season is this Old Navy skirt," says deals editor Rebecca Brown. "I love the idea of wearing it on a transitional day — maybe with an oversized quilted jacket. I think I’ll get a lot of wear out of it because it leans casual."
Another hint of leopard: Illude Ankle Bootie
- Affordable
- Thick heel; easy to walk in
- Too high of heel for some
Shade range: 9 | Size range: 6 to 11 | Material: N/A
While some might find the leopard print trend too bold, you can dress it down so the print isn’t too outside your comfort zone. Enter the leopard ankle boot: A favorite of associate editor Allie Wise.
“When it comes to fall, a classic block heel boot is a must! If I’m going to be walking around NYC, I need a thick heel to handle the walking,” she raved. “They are comfortable, chic and easy to slip on/off.”
Your new closet staple: H&M Single-Breasted Blazer
- Perfectly oversized
- Arms can run a bit short
Shade range: 5 | Size range: XS to XXL | Material: Polyester, rayon and spandex
"I got to keep this blazer after modeling it for a segment earlier this year and it immediately became a staple in my closet," said associate editor Kamari Stewart in our best blazers round-up. "I was on the hunt for a classic black blazer that was just oversized enough without feeling boxy and this one fits the bill. I can throw it over a tank top and jeans, a dress or a blouse and slacks. It works with everything."
Tackle two trends in one: Abercrombie & Fitch Paloma Mesh Top
- Very comfortable
- Fitted silhouette
- See through; needs a base
Shade range: 3 | Size range: XXS to XXL | Material: Polyester and elastane
Our experts predicted that mesh and leopard print would be trending for fall. What better way to embrace each trend by combining the two?
"I love this top so much! It pairs well with jeans, slacks and skirts and adds a trendy vibe to your look," mentions writer Jannely Espinal. "While it’s see-through, you can’t tell since the color of the fabric blends well with the skin. It looks elegant and features ruched details on the sides, which makes the fabric fitted to the body."
A basic you need: Khy Smooth Stretch Boat Neck Long Sleeve
- Smoothing and soft
- Can be worn off-the-shoulder
- Prefer more room? Size up
Shade range: 3 | Size range: XXS to 4X | Material: Nylon and spandex
I've been loving basics from Khy, a brand from television personality Kylie Jenner, because they don't miss out of quality. The price range for most of their basics are pretty accessible, and they're all equally thick, smoothing and soft in every way. I've especially been enjoying this long-sleeve for fall since it is also very lightweight for layering or wearing on it's own.
A cardigan and vest hybrid: Meshki Dionne Sleeveless Knit Vest
- Elevated cardigan
- Easy to layer
- Extra short sleeves
Shade range: 2 | Size range: XXS to 3XL | Material: Acrylic, polyester, wool and elastane
Meshki recently released their Archives collection featuring neutrals, knits and more fall essentials that you can wear in and outside the office. One of my favorite picks is this high neck cardigan. I mostly rely on cardigans for warmth, but I love that this one elevates your standard cardi with extra short sleeves and a sophisticated, fitted silhouette. I've loved wearing it on its own or underneath a blazer.
Add a pop of red: Vivaia Square-Toe Bow Ballerina Flats
- Basket weave detailing
- Deodorizing insole
- Anti-slip outsoles
- True to size
Shade range: 15 | Size range: 5 to 11 | Material: Knit and rubber
"I thought I swore off flats for good until I tried on this pair from Vivaia," raves associate editor Lauren Witonsky. "They’re cushioned in a way that feels like they would keep my feet comfy all day — from the arch support to the heel padding to prevent blisters." Although the ruby red is nearly out of stock, there are still other shades to choose from. "It’s the perfect pop of color to add to my otherwise neutral wardrobe!," she adds.
An everyday pant you'd want to sleep in: Buck Mason Surplus Rib Weekender Pant
- Highly comfortable
- Stretchy knit
- Runs long
Shade range: 8 | Size range: XS to XXL | Material: Cotton and spandex
"These pants are perfect to keep you cozy but also presentable in the fall for when you need to step, run errands or even go to work," boasts social media editorial assistant Annie Shigo. "I wore them with a blazer and they looked so chic. They are so cozy you’ll want to keep them on for bed."
Go bold with leopard: Abercrombie & Fitch Curve Love Mid Rise Slouchy Jean
- Multiple lengths
- Helps with waist gap
- Sizing goes quick
Shade range: 4 | Size range: 24 to 34; short, regular and long available | Material: Cotton
One of my favorite ways of styling the leopard print trend is through my bottoms, such as this denim pant from Abercrombie. I love that it comes in various lengths, widths and sizes, especially for a petite, curvy girl like me who deals with waist gap! But if you're still hesitant about the leopard print, the pant comes in classic washes, too, that I love wearing.
An elevated cardigan: Sezane Gaspard Cardigan
- Can be worn in two ways
- Embellished detailing
- Runs large; size down
Shade range: 19 | Size range: XXS to XXXL | Material: Super kid mohair, baby alpaca and recycled polyamide
We appreciate nothing more than a versatile cardigan. This one from Sezane can be worn in two ways: With the buttons face back to wear as a jumper, or worn forward to style as a cardi. Partnerships editorial assistant Erica Marrison has the red version, in particular, on her radar.
"I tend to gravitate toward neutrals since they’re easiest to mix and match with my other wardrobe staples (especially for office dressing), but lately I’ve had my eye on bright reds," she says. "My colleague Francesca Cocchi Zabloudil was wearing this cardigan recently and I had to ask her where it was from — it’s so beautiful in person." While that shade is nearly out of stock, there are 18 more to choose from, from bright blues to a warm beige.
Not just an ordinary long sleeve: Paige Caliban Top
- 100% cotton
- Full button front
- Hits right at hip
Shade range: 2 | Size range: XXS to XL | Material: Cotton
I've decided to take my basics more seriously, and have leaned towards ones with elevated details, such as this one from Paige. Rather than sticking to a simple tee or long-sleeve (which I equally love), I opted for this pick because it has subtle yet eye-catching details that make it stand out from my other long-sleeves. For instance, the sleeves are puffed and slightly ruched for a bit of a feminine flare.
A flat all about comfort: Rothy's The Max Square Mary Jane
- Cushioned insole
- Machine washable
- Sculpted outsoles
- Size up half a size
Shade range: 1 | Size range: 23 to 33 | Material: Cotton
One thing to know about Rothy's is that they're all about comfort. For instance, the insoles on these Mary Janes are highly cushioned, and are complemented by their sculpted outsole for stability and comfort all-around. Besides their attractive appearance, this is one of the reasons why these flats are high on production associate Audrey Ekman's fall wish list.
"I feel like Mary Jane flats are the 'it' shoe of the year, and Rothy’s are some of the comfiest out there," she says. "I’d style them with a pair of white crew socks or tights in the cooler months!"
A classic black jean: Good American Soft-Tech Good Petite Straight Jeans
- Inclusive sizing
- Highly comfortable
- Tons of stretch
- Best for 5’4 and under
Shade range: 1 | Size range: 00 to 32 | Material: Tencel, Ecovero, rayon, modal, polyester and lycra
I am usually very picky about my denim because I find most a bit uncomfortable. But one of my current favorites is this one from Good American. It has a unique SoftTech fabric (a combination of Tencel, rayon, lycra, to name a few) that truly doesn't make it feel like ordinary denim. The sizing is also super impressive as a petite curvy girl. Plus, you can't not have a black denim jean in your fall rotation.
Embrace the moto boot trend: Aldo Ryderr Ankle Boot
- Inner zipper
- Genuine leather
- Adjustable buckles
- Buckles jingle; tighten
Shade range: 1 | Size range: 6 to 10 | Material: Leather
Haven't tried the moto boot trend? Ekman suggests giving these Aldo boots a try. "Since they’re pretty edgy, I wasn’t initially sure how I would style them, but I’ve discovered that they’re actually super versatile — they’re kind of like your go-to leather jacket, but in boot form,” she says.
To have on rotation: Aritzia Babaton Innovate Blazer
- Removable belt
- Slimming silhoutte
- Structured and soft fabric
- Runs small; size up
Shade range: 4 | Size range: 00-16 | Material: Polyester, viscose, cotton and elastane.
This blazer from Aritzia checks all of my boxes: A fitted silhouette, tailored construction and a belted detail that makes the blazer stand out on its own. The belt is removable, so you can decide to wear it with or without depending on your styling goals. I've loved wearing it on its on or with a basic tee or tank underneath.
Frequently Asked Questions
Fall is all about cozy and lightweight attire, so you'll want your fabrics to encompass the same, too. "With the weather being so in between right now, I would stick to breathable fabrics like cotton, bamboo and merino wool," recommends Stein. "This will allow you to layer comfortably."
This fall will welcome the new and the old when it comes to trends. Chataigne says you should expect "the return of the love of chocolate brown, tan suede and red wine being the colors de jour" in boots, matching sets and everything in-between.
Red or oxblood, specifically, was a common prediction from our experts, so you'll want to add elements of the shade to your fall color palette. "Oxblood is great because the color is so rich it can be worn as anything from a pair of shoes to a lip stain , it all depends on your personal style," suggests Stein.
Fall will also be all about the details, from studs on denim and bags, along with "the new neutral love of animal print in leopard print and zebra," says Chataigne. Although leopard and other bold print can be intimidating, Stein suggests playing with accessories with the print, instead, this fall. "A pair of shoes or a handbag in leopard can give a monochromatic look some dimension," she adds.
"Build your outfit around a wine red or brown boot," says Chataigne. She adds that you can mix in a boho-style dress, keep it classic with a trench and chunky sweater or all of the above, with an oversized clutch or day bag. She notes, most importantly, to "not forget your third piece!"
How we chose
While choosing the best clothing and accessories for transitional weather from summer to fall, we interviewed stylists for their input. We also included editor favorites based on style and material. Many of the pieces we included are breathable for those warmer end-of-summer days, all while being lightweight enough for layering and staying on trend.
Meet the experts
- Christina Stein is a personal stylist based in New York City.
- Melissa Chataigne is a host, on-air beauty and fashion expert and stylist based in Los Angeles.
- Alex Rivera is at stylist at Stitch Fix.
Previous experts:
- Audrey Brianne is a celebrity wardrobe stylist.
- Natalie Bronfman was the costume designer for Hulu’s “The Handmaid’s Tale.
- Dana Asher Levine is a Hollywood stylist and DHStyle Inc. CEO.
- Cindy Conroy is a celebrity fashion stylist.
- Leesa Evans is a Hollywood costume designer and private stylist.
