Casual September outfits – Summer to fall casual transitional outfits and fashionable summer to fall casual outfit ideas here! Yes, here are some casual September outfits for all of you who wish to transition from summer to fall 2023 in style, though in your old casual clothes. Or perhaps in casual clothes from your transitional capsule wardrobe that you built the other day. Either way, scroll down to see the most stylish casual transitional outfits you could wear in September. Well, perhaps in October, too.

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WHAT TO WEAR WHEN TRANSITIONING FROM SUMMER TO FALL 2023

I know, coming up with the right casual transitional outfit idea that would let you transition from summer to fall in style can be quite challenging.

It’s either not warm enough to wear clothes from your summer capsule wardrobe. Or not enough cold just yet to wear the clothes from the capsule wardrobe you built for fall.

Furthermore, your summer clothes might not be fashionable anymore. Indeed, there are quite some pieces that will go out of style come September 2023.

Well, if you managed to build a transitional capsule closet with summer clothes that are still in style for fall 2023 and with a few last seasons clothes that are coming back in fashion for fall 2023, then you have an easier job to do. You have all the clothes that can be worn when transitioning from summer to fall 2023.

The only thing you need to do is to put them together in a fashionable way.

Don’t worry; I can help you with that. Scroll down to see 22 fashionable casual summer to fall transitional outfits now – 22 the best casual September outfits and stunning casual September outfit ideas!

FASHIONABLE CASUAL SEPTEMBER OUTFITS

By the way, all the collages below are hyperlinked and shoppable. Just in case you have misplaced your favourite summer dress that you planned to wear in fall and now looking for a new one.

Mentioning the summer dress, here is how to wear a summer dress in fall.

TRENDY CASUAL SUMMER TO FALL TRANSITIONAL OUTFITS WITH A DRESS

Here are some outfit ideas for all of you who want to transition your favourite summer dress into fall.

1 CUT-OUT DRESS WITH CARDIGAN AND POINTY FLATS

To transition your favourite summer cut-out dress into fall, style it with this season’s must-have layer – the cardigan. Yes, cardigans are very fashionable for fall winter 2023. Ps. Don’t forget to swap sandals for fashionable pointy flats.

2 ONE SIDE SHOULDER WRAP DRESS WITH A COLLEGE JACKET

A green one side shoulder dress is one of the most fashionable fall 2023 dresses. Hence you don’t need to bother what jacket and shoes you will wear with a green dress in early fall. You can even wear any jacket and any shoes from your capsule wardrobe.

However, you might want to wear pointy slingbacks and a college jacket – two of the key fall 2023 fashion trends.

Ps. If you like this look, but actually don’t have a green dress like this, nor feel like buying a one side shoulder dress for fall – get this green dress with long sleeves. It will be perfect for fall 2023 and spring 2023.

3 LITTLE RED DRESS WITH CUT-OUT ANKLE BOOTS

Finally, a little red dress with balloon sleeves – the most fashionable dress of fall 2023.

This summer to fall casual transitional outfit idea is actually for all of you who were thinking ahead and picked that popular balloon sleeve dress in red. Well, here is how to transition a red balloon sleeve dress into fall – wear it with fashionable lace-up ankle booties.

I advise you to put on cut-out Chloe Rylee boots (buy here) since these ankle boots are just perfect for fall. Besides, the cut-out trend will be quite strong this fall.

A pair of stylish sneakers is a good option, too.

4 MINI RED DRESS WITH SNEAKERS

5 SWEATER OVER A GINGHAM DRESS WITH BOOTIES

CHIC CASUAL SEPTEMBER OUTFIT IDEAS WITH SHORTS

Yes, shorts will be very fashionable in fall 2023, too! And here are some cool casual summer to fall transitional outfits with shorts you simply must try!

6 VEST WITH SHORTS AND SLINGBACKS

7 SHACKET WITH SHORTS AND SNEAKERS

8 CROPPED SWEATER WITH SHORTS AND RUBBER BOOTS

9 PONCHO WITH SHORTS AND SANDALS

EASY CASUAL SUMMER TO FALL TRANSITIONAL OUTFITS WITH A SLIP TOP

Slip top is probably the most effortless transitional piece from a summer capsule wardrobe. It’s easy to layer, plus it never goes out of style.

Here are my favourite casual summer to fall transitional outfits with a slip top.

10 SLIP TOP WITH BLUE JEANS AND SNEAKERS

11 CARDIGAN ON SLIP TOP AND BLUE JEANS WITH MULES

12 SLIP TOP WITH PLEATED SKIRT AND DENIM JACKET

Good news! Pleated skirts are back in fashion for fall 2023. Bring your favourite old pleated skirt into fall with a split top and chic denim jacket like I did.

Well, to be entirely honest with you, my pleated skirt is new, and it will be one of the key pieces in my 2023 fall capsule wardrobe. As you know, gold is one of the most fashionable colours this year and having at least one casual clothing in gold is simply a must for fall 2023.

SIMPLE CASUAL SUMMER TO FALL TRANSITIONAL OUTFITS WITH A WHITE T-SHIRT

Wait, I’m taking my words back. It’s even easier to transition a white T-shirt into fall.

See these chic, effortless summer to fall casual outfits.

13 WHITE T-SHIRT WITH BLUE JEANS TRENCH COAT AND STRAPPY SANDALS

Ps. This summer to fall casual outfit will let you transition the white t-shirt and strappy sandals.

14 MUSCLE TEE WITH LOW WAIST PANTS AND SNEAKERS

COOL SEPTEMBER OUTFITS WITH JEANS

15 BLUE JEANS AND WHITE T-SHIRT WITH HEELED LOAFERS

16 DENIM JACKET ON BLUE JEANS AND FLAT MULES

17 KNITTED TOP WITH CARDIGAN AND JEANS

CASUAL SEPTEMBER TRANSITIONAL OUTFITS WITH A SKIRT

And now, some really cute casual outfits for September with a skirt.

18 DENIM JACKET WITH A MINISKIRT AND FLUFFY SANDALS

19 CROPPED TOP WITH LONG TUTU SKIRT AND HIGH TOP SNEAKERS

20 T-SHIRT WITH A MINI SKIRT AND LEGGINGS

Last but not least, T-shirt with a mini skirt and leggings. Yes, wearing mini skirts with leggings is fashionable again. But, please, wear leggings with a mini skirt only like this – and only for your casual affairs in early fall.

COLORFUL SUMMER TO FALL CASUAL TRANSITIONAL OUTFIT

Finally, a summer to fall casual transitional outfit that will let you wear summer colours into fall.

21 RED ROMPER WITH A PINK THIN COAT AND STRAPPY SANDALS

CASUAL EARLY FALL OUTFIT WITH LEGGINGS

For the end, a casual September outfit with leggings.

22 TAILORED SHACKET WITH LEGGINGS

MORE OUTFITS TO WEAR WHEN TRANSITIONING INTO FALL AND CASUAL OUTFITS YOU CAN ALWAYS COUNT ON

Back to work already? Be sure to check work summer to fall outfits, too. By the way, what piece from summer capsule wardrobe do you wish to transition into fall the most? Up next: casual fall outfits.