Fashion blogger Veronika Lipar of Brunette from Wall Street wearing &OtherStories muscle tee Max Mara wide-leg pants for work

23 Back to Work Outfits to Wear in September and October

Work Outfits to Wear in September – summer to fall work outfits and summer to fall transitional work outfit ideas for all of you who are finally back at work! True, summer hasn’t officially ended yet and going back to the office sucks. At least compared to sipping a cocktail by the swimming pool. Still, it’s not all bad. Here are 23 summer to fall transitional work outfits that will keep you work-motivated for the last summer days. Trust me, once you see all these summer to autumn work outfits, you won’t mind working even though it’s still rather hot outside, and your friends are still sipping cocktails on the beach. Moreover, you will want to go back to work just to show everyone your new business style.

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HOW TO DRESS UP FOR WORK AT THE END OF SUMMER?

And we are back at the office. I hope you can say your summer wasn’t short. Well, you can’t say it ended too soon since there is still summer waiting for you outside, after 5pm. Only a few more hours, and you are heading back to the beach, right?

Anyway, since there is still officially summer and the weather knows it; here are 23 summer to fall work outfits and summer to fall transitional work outfit ideas for the last days of summer and first two days of fall 2021.

Here are summer to fall work outfits that require sandals and a light jacket or pumps but no jacket.

Nevertheless, some late summer work outfits smell a lot of autumn already. Well, I can’t help myself not to start wearing fall winter 2021/22 season already.

But don’t worry, I am showing you how to bring your favourite summer dress from the beach to the office and back. Just in case you are going back to the beach after working hours. I know I am!

WHAT TO WEAR FOR WORK AFTER THE SUMMER HOLIDAYS?

And here they are, 23 stylish late summer to fall transitional work outfits and summer to fall work outfit ideas you can wear into fall 2021!

Ps. All the collages are pinnable and hyperlinked – which means you can shop all the products simply by clicking on each product. A link will take you to the store where I found it at the most honest price.

CHIC SUMMER TO FALL WORK OUTFITS WITH A SUMMER DRESS

1 JW ANDERSON WHITE SHIRT DRESS AND BOLD PUMPS

Starting with the dress, I mentioned already – a white shirt dress that you can wear for 5* hotel brunch at the seaside or for the office.

Fashion blogger Veronika Lipar of Brunette from Wall Street wearing JW Anderson white shirtdress and pumps with a matching bag in the city in summer

By the way, you can see this late summer work outfit idea in motion, too. I have uploaded this outfit on Pinterest. Check it out to see how glorious this shirtdress is. You simply have to have it. Besides, the asymmetrical silhouette is one of the key fashion trends for fall winter 2021/22.

Well, if you don’t wear white after Labour Day, shop and save these summer to fall work outfits with a dress.

2 WHITE COLLAR DRESS WITH SHORT SLEEVES AND SLINGBACKS

The second summer to fall transition work outfit that you can wear in September 2021, is an oversized dress with a white-collar. White-collar dresses are some of the most fashionable fall dresses this season.

Ps. I have that Red Valentino dress with a collar, too. And it is my favourite September dress. Although things might change once I get the black and white collar dress.

3 BLACK AND WHITE COLLAR DRESS WITH PUMPS

This September 2021 office outfit with a dress will be perfect for any meeting, including a job interview.

In this September work outfit, you will look smart and reliable. And the leopard print pumps will make you look capable, fierce and brave to do whatever.

4 PUFF SLEEVE DRESS AND PLEXI PUMPS

The third dress you can wear for work on the last summer days is a fashionable red dress with puff sleeves.

Business woman Veronika Lipar of Brunette from Wall Street dressed in Lovers + Friends red dress Gianvito Rossi plexi pumps black top handle bag for a date in spring

Ps. If you don’t have a red dress yet, get one today (you can buy it here). A red dress is a must-have in a transitional wardrobe.

5 TWEED DRESS AND FLAT MULES

Tweed dress for work in September? I say, yes! I even say yes to a tweed dress for a wedding in September.

Here is how to wear a tweed dress in September. Ps. I will wear it like this, too. Oh, I just can’t wait to get this chic tweed dress. It’s Mango, and you are welcome.

Worry not; not all summer to fall work outfits I’m sharing with you today are dresses. Here are “not dress” summer to fall office outfits.

STYLISH SUMMER TO FALL TRANSITIONAL WORK OUTFITS WITH SHORTS

Finally, a late summer office outfit that is not a dress. Two summer to fall work outfits that are not a dress, actually.

I got plenty of new style ideas the moment I got my new dark blue tailored shorts.

Here are two of summer to fall transitional outfit ideas with shorts that are perfect for work in any office.

6 TAILORED SHORTS WITH A SWEATER AND KITTEN HEELS

7 PLEATED SHORTS WITH MATCHING BLAZER AND PUMPS

CUTE SEPTEMBER WORK OUTFITS WITH PANTS

From shorts to pants – here are two cute September office outfits with pants.

8 MUSCLE TEE WITH WIDE LEG PANTS AND SANDALS

Fashion blogger Veronika Lipar of Brunette from Wall Street wearing &OtherStories muscle tee Max Mara wide-leg pants

9 BABY CARDIGAN WITH STRAIGHT PANTS AND PUMPS

FASHION-FORWARD SUMMER TO FALL OFFICE OUTFITS WITH PANTS

And now three fashion forward summer to fall 2021 office outfits with pants.

10 LEOPARD PANTS WITH A BLACK BLOUSE

As leopard print is the No. 1 fashion trend of 2021, returning back to work in leopard print is for sure the smartest style choice you could make. Especially if you plan to change your work attire entirely, wearing more boss-lady fashion-forward pieces.

11 SWEATSHIRT ON TAILORED PANTS AND PUMPS

12 LEATHER TROUSERS WITH A SWEATER AND MULES

Ps. Be sure to tone down the edgy leather pants with a soft knit top. And no, my white sweater is not the only option. There are more office sweaters that go well with brown leather pants.

To be noted, burnt orange leather pants are very easy to style for the office. Almost as easy as the black leather pants.

Mentioning the black leather pants, here is a back to work outfit with black leather pants you simply need to try.

13 PINK BLOUSE WITH BLACK LEATHER PANTS

When you need to head back out after a long day, make life simpler with this outfit for the evening. Black leather pants and a pretty blouse take the guesswork out of dressing up; just step into a pair of statement shoes, and you will be out the door in no time. Well, you can actually wear these shoes to work, too. Malone Souliers mules are so comfortable!

Ps. Click on the blurry photo below to see the video of this chic work outfit.

14 SWEATER WITH SLACKS AND MULES

Love the business casual September work outfit I have just shown you? Then I bet you will love the next business casual September work outfit, too!

SEPTEMBER BACK TO WORK OUTFITS WITH JEANS

15 SILK SHIRT WITH JEANS AND PUMPS

LATE SUMMER TO FALL BUSINESS OUTFITS WITH A SUIT

Now, something you have been all looking for the most – summer to fall suits. Here are two late summer suits you can wear into fall 2021.

16 BLACK SUIT AND BLUE PUMPS

Mykonos Blue is one of the most fashionable colours of fall winter 2021 2022. Be fashion-forward and start wearing brisk blue clothes today! By the way, did you know that black is actually blue? Black is the darkest shade of blue. Anyway, here’s how to wear black and blue into fall 2021.

17 BLACK SKIRT SUIT AND FLATS

Ps. Be smart and invest in a quality blazer as you return to work this fall. Trust me, a quality blazer is a lifesaver. It will make you look presentable, smart, competent and feel fearless no matter what – just like a Hermes bag.

SUMMER TO FALL 2021 TRANSITIONAL BUSINESS OUTFITS WITH A SKIRT

And now six summer to fall transitional office outfits with a skirt. Two summer to fall work outfits with a pleated skirt, two more with a pencil skirt, that’s fashionable again, and two September work outfits with skirts that are a must have for fall 2021.

18 PINK PLEATED SKIRT WITH A FLOPPY TIE BLOUSE AND KITTEN PUMPS

IT Girl Fashion Blogger Veronika Lipar of Brunette from Wall Street wearing coral pink floppy tie blouse pink pleated midi skirt Ganni slingbacks pink top handle bag going to work in summer

This summer to fall outfit is perfect for teachers and all of you who are working with kids. Pretty pastel colours will bring some comfort to the kids in these strange times. Ps. You can style this cheerful fall work outfit with any of these pink face masks in the widget above.

19 T-SHIRT WITH PLEATED SKIRT AND SANDALS

If you want to look cool in front of the high school kids and gain their respect through your amazing style, furthermore be the IT teacher, the teacher with the best style, put on this cool skirt back to school outfit.

Ps. Be sure to put on a leather blazer if you are cold. Leather blazers are trending now.

And so are the leather skirts.

20 BLOUSE WITH LEATHER SKIRT AND PUMPS

21 BLOUSE WITH PENCIL SKIRT AND PUMPS

Guess what? Pencil skirts are back in style! Yes, pencil skirts are back in fashion for fall winter 2021/22.

Here is how to style a pencil skirt when you need to get dressed fast.

22 CROPPED SWEATER AND PENCIL SKIRT WITH PUMPS

And here is one more way to wear a pencil skirt to work this September. Style your new pencil skirt with a cropped sweater.

Fashion blogger Veronika Lipar of Brunette from Wall Street wearing H&M black pencil skirt red and pink cropped top Gianvito Rossi Plexi pumps

Ps. Better save both September work outfits with a pencil skirt – pencil skirts are the top 3 the most fashionable skirts of the season!

23 CROPPED SWEATER AND MINI SKIRT WITH SLINGBACKS

Finally, my favourite September work outfit with a skirt – a cropped sweater with a mini skirt and slingback.

MORE BUSINESS OUTFITS FOR FALL 2021 AND SUMMER TO FALL OUTFIT IDEAS

Feeling cold today? Check fall work outfits, then! Ps. Check summer office outfits if you are still working from your beach home. Up next: casual summer to fall transitional outfits.