Let’s face it: transitional dressing is difficult. Especially since it’s hot one minute and cold the next — and you’re both. While you cannot control the weather on any given day, you can control how you dress for it. That is sometimes easier said than done. Layering? Check. But what are the best methods? The answer is actually quite simple. Take a look at the street style set. A few things become clear as you scroll through some recent street style looks. First and foremost, midriff flossing and cut-outs aren’t just for the summer.
Crop tops aren’t either. Or, for that matter, bra tops. Blazers and lightweight jackets will come in handy. Keep your mini and midi skirts on hand. Also, be adaptable when it comes to footwear because temperatures can quickly change from warm to shockingly cool. You don’t have to set aside time to search the internet for inspiration because we did all of the legwork for you. We’ve gathered street style outfits that demonstrate the best ways to approach transitional dressing. Allow these fashion plates to serve as your guides for what to wear throughout September. And possibly even into October…
A high-low skirt comes in handy in this situation. Pair a nearly-maxi dress with a tank top, a statement jacket, and neutral heels.
The three-piece suit is a winter wardrobe essential. As September approaches, wear only the vest and slouchy trousers. When the temps really start to turn, put on the blazer and boots.
This summer, there was no denying that midriff flossing was popular. What’s good for your wallet? In September, you can keep the pieces in rotation. Pair a strappy maxi skirt with a cropped sweater in a complementary color. Kicks are a comfortable way to complete the look.
A white button-down under a belted blazer is the ideal complement to bike shorts. Finish with chunky boots and you’re ready to go.
Yes, you can still wear bra tops after summer is over. Wear a coordinating blazer on top and a high-waisted midi skirt in a different color. Colorful pumps complete the look.
Combine a cropped sweater and shirt with a skirt with a thigh-high side slit. Finish the look with some gleaming footwear.
Layer one cropped top over another, and wrap a colorful sweater around your shoulders. (Bonus points if the knot is not perfectly centered.) Finish with high-waisted pants and sandals that complement your sweater.
As the weather begins to cool, this is how to wear cut-out tops. Combine your favorite long-sleeved look with coordinating pants and boots.
Who says you have to match everything? With creamier Bermuda shorts and a black top, a bright white blazer looks super cool. Black ankle-strap pumps complete the look.
By leaving a striped button-down open, you can embrace the visible bra trend. Put on a blazer and black heels after tucking your shirt into belted pants.
Think light when it comes to layers. To keep your legs (somewhat) warm, layer a long, sleeveless jacket over a basic white tee and miniskirt combo.
Don’t put those see-through tops away just yet. They go perfectly with baggy leather pants.
In a backless top, show a little skin. Wear slightly baggy khakis underneath.
A cropped blazer and a pleated skirt with a large side slit will keep you warm while still looking stylish.
Wearing lighter leather is also acceptable. Cover up a bare top and creamy midi skirt with a matching leather jacket for a summer-meets-fall look.
Longline blazers, especially brightly colored ones, look great as dresses. For a unified look, choose a pouch and sandals in similar colors.
Skirt suits will be popular this fall, so get ahead of the game with a heavyweight jacket and matching miniskirt. Colorful sandals can be worn now, and neutral ankle boots can be worn later.
Wear a tan sleeveless sweater with light-colored khakis to stay neutral. For a truly balanced look, add a chunky chain necklace and barely-there sandals.
A slightly off-the-shoulder knit top is an excellent choice for dealing with inclement weather. You’ve got it made with rolled jeans and sandals.
This is where the ever-present padded skirts come into play. Wear yours with a light gray sweater that is half-tucked into the skirt. White boots FTW.
Suits in lighter colors and fabrics are totally acceptable. Look for cropped trousers that allow you to show off your favorite strappy sandals.
Pull out your wool trousers and complement them with a short-sleeved shirt. Berets are optional.
Stay cool and cozy in a jumpsuit that shows a little skin.
By wearing a button-down underneath your favorite strapless dress, you can make it seasonless.
During the transitional season, a cropped jean jacket is a must-have. Feeling daring? Try pairing your jacket with a bustier top and a different wash of jeans.
Mix prints to show off your sartorial prowess. A tie-dye jacket, a black top, an embellished skirt, and two-tone ankle boots may not look good on paper, but they look great in person.
Cropped sweaters with strategic cut-outs look great with high-waisted midi skirts. We recommend wearing the chain-link anklet with the quilted heels.
You can avoid overheating by wearing a sweater with split sleeves. Particularly when paired with leather pants.
Layer on top while showing a lot of leg. Wear a lightweight V-neck sweater over a zip-up top, then add a logo-embellished miniskirt, socks, and high-heeled shoes. When the weather is unusually cool, throw on a blazer.
Wear a cropped sweater with light slacks. If you’re worried about getting cold, layer a complementary jacket on top.