Transitional Dressing Outfit Ideas

Let’s face it: transitional dressing can be really hard. Especially since it’s warm one minute and freezing the next — and so are you. While you have no control over how the weather is on any given day, you do have control over how you dress for it. That can be easier said than done. Layering? Check. But the best ways to do it? Well, the answer is really quite simple. Turn to the street style set. If you scroll through some recent street style looks, a few things become crystal clear. First, midriff flossing and cut-outs aren’t strictly for summer. Neither are crop tops. Or bra tops for that matter. Blazers and lightweight jackets will be your saviors. Keep your mini- and midi-length skirts in play. Plus, be flexible when it comes to footwear since things can go from warm to shockingly cool in an instant. You don’t have to set aside time to search the internet for inspo because we went ahead and did all the hard work for you. We’ve rounded up street style outfits that exemplify the best ways to go about transitional dressing. Let these fashion plates be your guides for what to wear all the way through September. And maybe even well into October…

Images: Imaxtree

Transitional Outfits 2020

Transitional Outfits 2020 #1

This is where a high-low skirt comes in rather handy. Combine an almost-maxi version with a tank top, a statement jacket and neutral heels.
Transitional Outfits 2020 #2

The three-piece suit is a cold-weather staple. Flaunt just the vest and slouchy trousers as we enter September. Then work in the blazer and boots once the temps really begin to take a turn.
Transitional Outfits 2020 #3

There’s no denying that midriff flossing was everywhere this summer. The good news for your wallet? You can keep pieces in rotation in September. Style a strappy maxi skirt with a cropped sweater in a similar shade. Kicks are a comfy way to complete the outfit.
Transitional Outfits 2020 #4

A white button-down worn under a belted blazer is the perfect topper for bike shorts. Cap things off with chunky boots and you’re all set.
Transitional Outfits 2020 #5

Yes, you can still sport bra tops after summer wraps up. Just wear a coordinating blazer on top and a high-waisted midi skirt in an alternate hue. Colorful pumps polish off the look.
Transitional Outfits 2020 #6

Balance out a cropped sweater and shirt combo with a skirt boasting a thigh-high side slit. Wrap up the look with some shiny footwear.
Transitional Outfits 2020 #7

Layer a cropped top over another cropped top and tie a colorful sweater around your shoulders. (Bonus points if the knot is off-center.) Finish things off with high-waisted pants and match your sandals to your sweater.
Transitional Outfits 2020 #8

Now this is how to rock cut-out tops as we move closer to cooler temps. Team your favorite long-sleeve take with pants in a similar shade and complementary boots.
Transitional Outfits 2020 #9

Who says you have to match? A bright white blazer looks über cool styled with creamier Bermuda shorts and a black top. Black ankle-strap pumps round things out nicely.
Transitional Outfits 2020 #10

Embrace the visible bra phenomenon by leaving a striped button-down open. Tuck said shirt into belted pants, then slip on a blazer and black heels.
Transitional Outfits 2020 #11

When it comes to layers, think light. Slip on a long, sleeveless jacket over a basic white tee and miniskirt combo to keep your legs (somewhat) warm.
Transitional Outfits 2020 #12

Don’t put away those see-through tops just yet. They’re the perfect partner for baggy leather pants.
Transitional Outfits 2020 #13

Show a little skin in a backless top. Keep covered below with slightly loose khakis.
Transitional Outfits 2020 #14

A cropped blazer and a pleated skirt with a significant side slit will keep you warm while looking cool.
Transitional Outfits 2020 #15

You can also get away with wearing lighter leather. Cover up a nude top and creamy midi skirt with a coordinating leather jacket for real summer-meets-fall vibes.
Transitional Outfits 2020 #16

Longline blazers work great as dresses, especially brightly colored ones. Pick a pouch and sandals in similar shades for a cohesive feel.
Transitional Outfits 2020 #17

Skirt suits are going to be big this fall so get a jump on the trend with a heavyweight jacket and matching miniskirt. Add in colorful sandals now, switch to neutral ankle boots later.
Transitional Outfits 2020 #18

Stay neutral by teaming a tan sleeveless sweater with light-colored khakis. Work in a chunky chain necklace and barely-there sandals for a truly balanced look.
Transitional Outfits 2020 #19

A slightly off-the-shoulder knit top is a great way to tackle unpredictable temps. Throw in rolled jeans and sandals and you’ve got it made.
Transitional Outfits 2020 #20

This is where those ubiquitous padded skirts come into play. Top yours with a light gray sweater half tucked into said skirt. White boots FTW.
Transitional Outfits 2020 #21

You can totally rock suits in lighter shades and fabrics. Look for ones that include cropped trousers so you can still flaunt your favorite strappy sandals.
Transitional Outfits 2020 #22

Dig out your wool trousers and polish them off with a short-sleeve shirt. Beret optional.
Transitional Outfits 2020 #23

Stay cool and cozy with a jumpsuit that reveals slivers of skin.
Transitional Outfits 2020 #24

Make your go-to strapless dress seasonless by sporting a button-down underneath.
Transitional Outfits 2020 #25

A cropped jean jacket is a necessity during the in-between season. Feeling bold? Try styling your jacket with a bustier top and jeans in a different wash.
Transitional Outfits 2020 #26

Go ahead and flex your sartorial muscle by mixing prints. A tie-dye jacket, a black top, an embellished skirt and two-tone ankle boots may not translate on paper, but they work well IRL.
Transitional Outfits 2020 #27

High-waisted midi skirts call for cropped sweaters boasting strategic cut-outs. We highly recommend incorporating the chain-link anklet and quilted heels.
Transitional Outfits 2020 #28

A split-sleeve sweater can prevent you from overheating. Especially when you pair it with leather pants.
Transitional Outfits 2020 #29

Layer up top, but show a lot of leg. Wear a lightweight, V-neck sweater over a zip-up top, then work in a logo-clad miniskirt, socks and fancy footwear. Add in a blazer when it’s unusually cool.
Transitional Outfits 2020 #30

Style a cropped sweater with light-colored slacks. Drape a complementary jacket on top if you’re worried about getting cold.