Our editors have independently selected the items featured in this article because we think they’re worth knowing about. Shop TODAY has affiliate relationships so we may get a small share of the revenue if you buy something through our links.
So we consulted style expert Brooke Jaffe to help guide us on our transitional style quest.
“The key to transitional dressing is layering and color-coordination,” said Jaffe. “The easiest way to update a sleeveless maxi dress or slip dress is layering a fitted T-shirt or turtleneck underneath.”
None of us are made of money (and lucky you if you are!) so to start, here are three things that belong in your closet right now.
A leather or vegan leather jacket in black, which “can be layered over your summer maxis, jeans and tees and blouses. There is nothing it doesn't instantly update. Look for ones that are a little more cropped. They look newer and are flattering with dresses and all of the higher-rise denim out there,” said Jaffe.
Come Together California CTC Womens Dressy Vegan Leather Biker Jacket, $35, Amazon
Make like Jessica Simpson, who loves leopard prints, and get one of your own.
“I also think traditional leopard looks chic with grey denim which is another emerging trend. If you don't feel confident investing in a statement leopard dress or coat, buy a scarf or pair of leopard flats to add to small touch of the trend to your look," said Jaffe.
Tapp C. Fashion Leopard Print Infinity Scarf, $10, Amazon
As for accessories, you need a bucket bag.
“This is the new shape to have and to hold in accessories and will make all your clothing for fall look fresh,” said Jaffe, who loves a bright red. “Shades of brown and black are also incredibly chic and versatile. The new bag silhouette alone will do a lot of the talking.”
TOPSHOP Bucket Bag, $45, Nordstrom
And for our own personal must-have: a classic, simple and totally timeless jersey top, which goes easily with jeans, skirts and anything in between.
LAFAYETTE 148 NEW YORK Crewneck Jersey Tee, $148, Nordstrom
Transitional fashion fundamentals
"The white jean and gingham shirt are the quintessential summer look. Menswear shirting continues to be one of the biggest trends in fashion but its always a classic look we can rely on time and time again. I like to pair white shoes of all kinds with this look. Hoops are the earring of the moment, and this look features a high-shine pair. For her bag, we wanted to feature a statement bag and this one is straw. Remember, straw is no longer just for the beach anymore!" said Jaffe.
Stuff We Love
Relaxed Boy Shirt in Crinkle Gingham, $60, J. Crew
Mid-Rise Rockstar Super Skinny Jeans, $29, Old Navy
Large Tube Hoop Earrings, $20, Express
Bamboo Homemade Tote Bag, $38, Amazon
“Despite the taboo that you can’t wear white jeans outside of the summer months, yes, you can! It’s all about carrying the white jean forward into fall by incorporating ideas like animals prints. White jeans look elegant styled with shades of brown, camel and leopard,” said Jaffe.
ASOS DESIGN Fluffy Sweater, $35, ASOS
ASOS Stradivarius Camel Tailored Coat, $95, ASOS
AE NE(X)T Level Jegging, $50, AE
Forever 21 Faux Leather Bag, $23, Forever 21
Aldo Leather Heeled Ankle Boot, $82, ASOS
"There is going to be a lot of traditional leopard print out there and it's a great investment print because you can style with white jeans and then ease your way into black," said Jaffe.
Parisian Belted Leopard Coat, $64, ASOS
Circular Metal Earrings, $20, Zara
Raid Maple2 Black Patent Loafers, $48, ASOS
"The summer striped T-shirt is a classic, and we modernized it by pairing it with a white denim skirt — it’s the new wardrobe must-have," said Jaffe.
Lace-Up Denim Mini Skirt with Raw Hem, $80, J. Crew
Classic Striped T-Shirt, $50, J. Crew
Steve Madden Greece Sandals, $37, Macy's
Polly Hoop Earrings, $34, Bauble Bar
"Try pairing the striped shirt for fall with a vegan leather pencil skirt. It’s a great transitional look that is polished yet comfortable," said Jaffe. "This is a look that can take you from desk to dinner."
Striped Flame 3/4 Sleeve Boatneck Top, $68, Lilla P
Mosman Leatherette Black Skirt, $100, Universal Standard
H&M Long Jacket, $35, H&M
Easy Street Proper Dress Pump, $12-$60, Amazon
Le Meridien Black Bucket Bag, $37, Lulus
"We all have our go-to floral dress. It’s our style version of comfort food. You can update the look with resin earrings and a straw circle bag," said Jaffe.
Molokai Floral Maxi Dress, $89, Coedition
Round Raffia Crossbody Bag. $50, Zara
Large Polished Gold Ends Hoop Pierced Earrings, $75, Coedition
Lauren Conrad Firefli Sandals, $13, Kohl's
"You want to find shirts and tops that fit well, and can serve as your base layer under your dresses. Here, we used a fitted black T-shirt — which you may already own — and a vegan leather jacket to ward off the chill on cooler days. We added a red bag for a dash of color. Another variation? Wear a turtleneck underneath!" said Jaffe.
Play It Koi Black Foral Print Surplice Maxi Dress, $47, Lulus
Souped-Up Black Vegan Leather Moto Jacket, $70, Lulus
Slim Perfect T-Shirt, $30, J. Crew
Lucy Chevron Quilt & Lock Clutch Chain, $14, Boohoo
Shop TODAY takes care to recommend our favorite items chosen by trusted experts and editors, as well as inform our readers of great deals, customer favorites, and newsworthy products from around the web. For more on our process, click here.