Early fall work outfits and 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 the best early fall outfits 2025 – 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. What is more, you will want to go back to work just to show everyone your new business style.

OGLAS I get a commission for purchases or clicks made through links in this post.

And we are back to work and long hours 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?

Giving there is still officially summer and the weather knows it; here are 30 summer to fall work outfits and summer to fall transitional work outfit ideas for the last days of summer and the first two days of fall 2025.

Here are summer to early fall work outfits that require sandals and a light jacket (blazer) 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 2025/26 season already.

As we turn the corner on vacation dressing, it is time to consider that transitional period when we start assembling our autumn wardrobe.

Even so, 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!

THE BEST EARLY FALL WORK OUTFITS 2025

And here they are, 30 stylish late summer to fall transitional work outfits and summer to fall work outfit ideas you can wear into fall 2025!

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.

To find out more about the garments (size, fit, where I bought it), subscribe to Brunette from Wall Street Substack. I’m sharing this info with free subscribers, too. But you will want to upgrade your subscription whatsoever. Benefits of paid subscribers: fashion trend reports for AW25/26 and SS26 (essential for Fashion Influencers, Fashion Designers and people working in Fashion Business/Retail), Dress Code Guides (essential for EVERYONE).

FASHIONABLE BUSINESS CASUAL EARLY FALL WORK OUTFITS

It is time to pick up the pace as life returns at full speed. There is a thrilling jolt of fall energy in the city as we go back to work.

As you manage a full day’s schedule, you will need these business casual early fall work outfits that are equally hard-working.

1 BLACK TURTLENECK SWEATER WITH CAPRI PANTS AND KITTEN HEEL SLINGBACKS

Return to the office looking the most fashionable yet. Nail the demure girl aesthetic in a fashionable black turtleneck sweater and capri pants styled with kitten heel slingbacks.

Your reflection in the mirror will show confidence, and as you leave home in your meticulously curated Max Mara black 3/4 sleeve turtleneck virgin wool top, Max Mara black capri pants, and Gucci slingbacks, a whirlwind of emotions will dance within you.

Stepping out of your front door in black capris, you will feel like Holly going to work for the first time, while looking like Audrey. The world outside may be bustling with the usual commotion, but your outfit will exude an air of quiet luxury and sophistication, commanding attention without a word.

Making your way to work, the black turtleneck will give you the warmth and comfort you seek when returning back to the office in the cold autumn chill.

I love the three-quarter sleeves for season’s change and days of pumpkin-spiced lattes and falling leaves.

At the same time, capris are a revelation – tailored to perfection, they elongate your legs and provide a powerful silhouette. The black hue effortlessly complements the turtleneck sweater, creating a seamless fit that speaks of demure and style.

And once you put on Gucci slingbacks, you feel like you can conquer the world, one confident step at a time. A pair in patent leather and liqueur red will elevate your outfit from ordinary to extraordinary. And since you will be able to walk in them effortlessly, nothing can stop you today.

2 RUFFLED RED SILK BLOUSE WITH A PENCIL SKIRT AND SLINGBACK PUMPS

Step forward in a midi pencil skirt that injects energy into the back to work mood. A pencil skirt looks equally fabulous paired with 5DEN tights and slingback pumps or boots when the cold weather comes.

For a more fashion-forward style, try a modern midi length with a high-slit to keep things interesting. By the way, the column slit skirt is our favourite skirt trend.

But what happens when you pair that skirt with the perfect blouse? Magic. Picture yourself walking into the office with confidence, wearing a red ruffled silk blouse. The vibrant red hue brightens up your outfit and your entire day. It’s a colorthat exudes power, passion, and a touch of daring sophistication. And it’s the colour of the season for work.

Correspondingly, the ruffled details add a playful touch – not too much, we still want to keep our look professional and demure. Even so, let yourself show that you’re not afraid to express your personality, even in a corporate setting. It’s a blouse that strikes the perfect balance between being bold and maintaining a sense of professionalism.

Finish the look with Aquazzura black Kiki slingback pumps or Amina Muaddi Begum Swarovski crystal-embellished satin slingbacks if you are grabbing drinks after work. They both look exceptional. The pointed toes will elongate your legs, giving you an extra dose of confidence. Pov You will feel like you’re walking on a runway when heading to your desk.

TRENDY PRE FALL FASHION OUTFITS FOR WORK

Stay on trend with these fashionable pre fall outfits or return to the office looking the most fashionable yet. Midi pencil skirts and chic tailoring dazzle for meetings or pick from a whole array of options in red, black, grey or leopard.

3 LEOPARD PANTS WITH A NAVY BLAZER AND BLACK BLOUSE AND BLUE COURT SHOES

Go for a more exceptional fashion forward option instead of the usual trousers and slacks. Leopard print pants are again at the beginning of their life cycle, and looking at the fashion trend predictions, this micro fashion trend will last throughout the season paired with a black blouse and navy blazer later in fall.

4 SHORT BLACK DRESS WITH KITTEN HEEL SLINGBACKS

Precisely executed, traditional tailoring gets a relaxed update this season with kitten heels. Completely reimagined in patent leather, it is high time to wear kitten heel slingbacks.

5 BLAZER AND SHORT DRESS WITH KITTEN HEEL PUMPS

When you need to head back out after a long day, make life simpler with this outfit for the evening. Black jacquard blazer and a pretty dress 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. Stuart Weitzman kitten heel slingbacks are so comfortable! I only wish they weren’t made of suede. I hate suede as a fabric. It’s the second most monstrous material. The first is corduroy, of course. Ps. Burn your suede boots. They won’t do you any favour.

FASHIONABLE LATE SUMMER TO FALL BUSINESS FORMAL EARLY FALL OUTFITS WITH A SUIT

Putting together an outfit in cooler weather can get more complicated with all the extra layers. Simplify matters by investing in a trendy suit that easily integrates into your daily wardrobe and can work together with your other favourite separates to create endless options throughout the season.

6 BLACK PANTSUIT WITH MARY JANE PUMPS AND A HEADBAND

A black pantsuit with a sleek black blazer and chic skinny pants will give you infinite style options worn together or separately with a camel sweater or layered over/under your favourite summer dress.

7 BLACK WIDE-LEG PANTSUIT AND POINTY FLAT MULES WITH A HEADBAND

If you are not ready to leave home in the trendiest fall pants yet, nor let the summer go and embrace closed shoes, try this early fall work outfit.

8 AUTUMN PANTSUIT WITH 80s STYLE BLAZER AND MESH BALLET FLATS

Even so, you might want to streamline your autumnal workwear with a chic pantsuit in mid-seasonal colours of blond and mesh ballet pumps.

Mesh ballerinas are the only accessory you need for a smart prefall look that never feels overwrought and can be worn from the morning business meeting to happy hour at the new bar.

9 BLACK DOUBLE BREASTED PENCIL SKIRTSUIT AND POINTY BALLET FLATS

Keep your wardrobe ticking over as we approach the end of summer. A double-breasted blazer is easily layered over a knee-length skirt and paired with pointy ballet flats for Mondays that don’t end.

FASHIONABLE EARLY FALL BUSINESS SMART FALL OUTFITS

Venture beyond the co-ord sets; this season, easy separates take center stage.

10 DOUBLE BREASTED BLAZER ON BROWN WIDE-LEG PANTS AND SLINGBACKS

Picture, a pair of rich brown trousers, yes, I have luxurious brown Max Mara trousers in my mind. I love them and I know they will become your style staple. They effortlessly pair with a simple tank top and a commanding black double-breasted blazer. Btw mine is from Pinko.

IMAO, brown pants and black blazer channel confidence, a must-have attribute in any workplace setting.

To finish this business smart outfit, set your sights on none other than the Valentino Garavani Rockstud kitten heels. They are comfortable and back in fashion. The trend is micro, but those kitten heels ensure effortless movement, while the unmistakable Rockstud embellishments impart a dash of opulence and individuality to your overall look.

CUTE EARLY FALL WORK OUTFITS THAT MEET CASUAL BUSINESS AND CHIC

Banish the thought of workwear as bland and pragmatic. Here are two cute early fall work outfits that offer smart options for the day, feisty looks for a contemporary mood and form-fitting styles that are designed to thrill. Open your eyes to fresh possibilities for fall 2025.

11 SHORT SLEEVE SWEATER WITH HOUNDSTOOTH PANTS AND FLATS

An unexpected print is a key to designs with young, fresh energy. From houndstooth to black, leave behind plaid and grey and give your spirits a boost.

POV Houndstooth pants work equally well with black long sleeve turtleneck and sneakers for a more boyish charm after office hours.

12 STRIPED CARDIGAN WITH NAVY BLUE PUDDLE PANTS AND BALLET FLATS WITH A HEADBAND

One thing we love about the cool weather dressing is the return of a soft, chic cardigan. For the beginning of September, choose a striped cardigan and pair it with wide-leg puddle pants and ballet flats to make sure you keep up with the busy schedule and errands.

As the brisk September breeze starts to make its presence felt, there’s a certain comfort in slipping into a cardigan. It provides just the right amount of warmth without stifling your style. The timeless stripes add an element of sophistication to your fit, and they’re a nod to classic fashion with a modern twist.

Beneath your cozy cardigan, opt for a striped shirt to play with patterns and textures. The combination of stripes creates a harmonious yet dynamic American old money club look that effortlessly transitions from the office to after-work social gatherings. It’s the kind of style that is chic while still exuding a professional charm.

To anchor your outfit, choose navy blue puddle pants. My wide-leg pants are comfortable and incredibly flattering. They will elongate your legs and provide a graceful silhouette that complements the cardigan and shirt combo beautifully on you, too.

When it comes to footwear, opt for gold ballet flats. The golden hue adds a touch of opulence to your outfit, making you shine even on the busiest of days. But don’t ask me about mine, because they are old – like super old.

Complete your look with a headband. Our favourite accessory can make a big impact by adding a touch of preppy charm to your outfit. It keeps your hair in place and frames your face, giving you a polished and put-together appearance.

SHOES: gold ballet flats – I bought mine a life time ago in Italy – luckily my shoe size hasn’t changed since and I can still wear them whenever I want to wear cutesy shoes. These come close.

SIMPLE PRE FALL WORK OUTFITS

Knits and dresses are the fashionable answer to all-day comfort as the chill starts to creep in. Look to simple silhouettes for the old money office vibe.

13 RED SILK BLOUSE WITH DARK DENIM AND POINTY FLAT MULES

Whether it is dressed up for home or casual for the corner office, a silk blouse and dark denim jeans are the easiest items to throw on. They are the perfect transitional items that work equally well with flat mules or loafers. I, of course, wear them with designer slippers.

14 SHORT SLEEVE KNIT DRESS WITH SLIDES AND A SUMMER BAG

Navy short sleeve dresses are the easiest outfit to put together if you are rushed for time. Just step into precious slides and go! We love simple office dresses, which allow you to transition your summer raffia bag from the beach to the office.

ELEGANT SUMMER TO FALL WORK OUTFITS WITH A SUMMER DRESS

Prolong those days of leisure by throwing new tailoring over your favourite summer dress, or choose smart styles in opulent tones to give added radiance to your tan.

15 BLAZER ON SUMMER WORK DRESS STILETTO HEELS

Warm up your fall work wardrobe with rich blues. Navy blue dresses are here to add an extra autumnal charm.

Bold and rich is the way to go when thinking about wearing colors in cooler weather. Choose shades like navy blue or cherry liquor red that sit well alongside fall staples of brown and black for look that work in perfect harmony.

And rewear your favourite summer dress with a dapper blazer in a matching hue and precious pumps.

STYLISH SUMMER TO FALL TRANSITIONAL WORK OUTFITS WITH SHORTS

Shorts are such an exquisite garment, and we just love the ones that look smart and office appropriate. Make it super professional with designs that come in black or navy blue or add an extra dimension with boucle fabrics shot through with metallic threads that glint when they catch the light.

16 RED SILK BLOUSE WITH SHORTS AND MARY JANE PUMPS

Even though the no pants fashion trend with super short shorts is out of the question for work, shorts don’t have to be tailored and long in order to be suitable for work in early fall. In fact, extra details like pockets and buttons give additional possibilities to make the transition from home office to corporate daytime. But you need to pair them with black opaque tights. The shorter the day, the more opaque the tights.

And treat yourself to navy blue shorts with golden buttons to add little luxurious touches that will lift the spirits on foggy mornings.

Try navy blue shorts with red ruffle bouse. A blouse with an ornate finish around the neck (see the product gallery below) is a great way to add interest to your outfit. Look for designs to wear under jackets and blazers once it chills down.

FASHIONABLE SEPTEMBER WORK OUTFITS WITH TROUSERS

There is so much on offer beyond the traditional pre fall basics with slacks and cady pants. As the days get shorter, why not contemplate a more fashionable leg style this season?

It is time to start thinking about cool weather dressing, and we are enamoured with demure sets in minimalist block shades. Soft cardigans and knitted turtlenecks pair so well with high waisted pants and are perfect options to carry you seamlessly from home comfort to the office and IRL meetings. Put the ease back into everyday dressing with this back to office autumn outfit.

17 TURTLENECK WITH HIGH WAIST PANTS AND KITTEN HEELS

Buy into our favourite trouser trend and get high waisted wide leg pants. Style them with a halterneck top to give an added kick or indulge in some retro nostalgia with burgundy.

When it comes to the colour of the season, there is nothing better than burgundy and cherry liquor red. Either in glossy or something more tangible like a headband.

18 BLACK TURTLENECK SWEATER WITH BLACK LOW WAIST TAILORED PANTS AND SNEAKERS

Now I know you want to transition your Sambas and Gazelles to fall 2025. Even though you know they are past due. But wear them with puddle pants when you are looking for a sleek put-together silhouette within casual business code.

For the silhouette, we love the high waist for a slightly more demure fit.

Grey pants paired with a merino wool turtleneck top will be perfect as the mornings get colder, but afternoons warm up as you leave your corner office.

SUMMER TO FALL 2025 TRANSITIONAL BUSINESS OUTFITS WITH A SKIRT

Summer may be drawing to the close, but skirt season is far from over. All in all, a new skirt always gets us in the mood for work.

19 WHITE OVERSIZED T-SHIRT WITH LONG COLUMN SKIRT WITH A SLIT AND SLINGBACKS

As the sun dips lower in the afternoon sky during early fall, the energy in the office is going down. Bring fresh energy to your desk with a crisp white cotton T-shirt. Pov there is something magical about wearing white in autumn. Perhaps, because of that “no white after Labour Day” rule you have in the USA. Be that or something else, a white oversized T-shirt, with its luxurious fabric blend, complements the transitioning seasons and adds a touch of freshness to the office environment.

Pair it with a dark column skirt. A long pencil skirt, with a side slit, offers a glimpse of your confident stride. The skirt will elongate your silhouette and make you look so fashionable. Remember, this is still one of the most fashionable skirt of the season. It is the key trend for fall winter 2025/26 and will offer you the perfect balance between looking professional and feeling special.

Finish with black slingback pumps with curvy heels. The black hue provides a chic contrast to the pristine white T-shirt and adds a touch of drama to your outfit. The curvy heels will ensure comfort and flexibility, allowing you to move seamlessly through your afternoon meetings and tasks.

POV This September 2025 office outfit with a skirt will be perfect for any meeting, including a job interview.

In this September work outfit, you will look smart and reliable. And the white T-shirt will make you look capable, fierce and brave to do whatever.

20 CAMEL SWEATER WITH PLEATED MIDI SKIRT AND PUMPS

Play with pleats and knits for daytime affairs and make the switch from light pastels to dark blue tones. Look to deeper hues as an alternative to playful florals, they will look luscious amidst the fall landscape.

SEPTEMBER BACK TO WORK OUTFITS WITH JEANS

Or seize the denim trend and use it as an excuse to bring some denim into the mix.

As the crisp breeze of early fall rustles through the trees and leaves start to scatter on the pavement, denim is giving.

21 DOUBLE BREASTED BLAZER ON A BLACK TANK TOP AND STRAIGHT JEANS WITH SLINGBACK PUMPS

Just picture the morning sun casting a gentle, warm glow as you step out onto the bustling streets on your way to work. You are walking down the street, slightly faster as you are running late – again. Yet exuding confidence and grace in a navy blue Sandro Paris double-breasted blazer.

Its structured silhouette is giving a touch of professionalism to your outfit, while the deep navy hue is bringing preppy.

Beneath the blazer, a simple yet versatile black tank top (POV rumour has it you have slept in that top a night before – I didn’t, though) provides a chic foundation for your fit. Its minimalist design goes with the latest styling trends.

Sézane straight raw blue jeans are our go-to choice for a touch of casual yet chic. Btw I’m wearing Brut sexy, but you might need to choose a wider fit for this silhouette. You need modern skinny jeans with wider hem if you want to pair them with black slingbacks.

22 OVERSIZED DOUBLE BREASTED BLAZER WITH DARK WASH SKINNY JEANS AND PUMPS

Embrace the fun of wearing jeans for the office and get ready for work in an oversized blazer and heels.

23 OVERSIZED BLAZER WITH BLUE JEANS AND SNEAKERS

On the other hand, blue jeans and oversized blazers are perfectly suited for busy days. Pair with chic sneakers if you need to go places.

24 POLKA DOT BLOUSE AND WIDE-LEG JEANS WITH POINTY BALLET FLATS

A striking bow is the only adornment you need for an early fall work outfit with jeans that never feels overwrought.

25 OVERSIZED GREY BLAZER WITH BLUE SKINNY JEANS AND WHITE T-SHIRT WITH POINTY SLINGBACKS

A brand new pair of jeans is the ultimate confidance boost. From wide-leg jeans, I have just bought to the blue skinny jeans I have been having for years and you will soon wear on a daily, step out in our favourite look of the season.

The return of skinny jeans brings back our favourite style formula: skinny jeans and blazer. Obviously, in an updated, modern way, paired with pointy kitten heel slingbacks. Gucci, again! Girl math!

COMFORTABLE EARLY FALL WORK OUTFITS FOR WORK FROM HOME

Now the weather is cool enough to wear smart tailoring with ease and bring chunky knits into the mix; we love the options on offer for our home office.

26 RED CARDIGAN WITH WOOL PANTS AND FLATS

A snug knit top or a pretty cardigan, it is important that our bodies feel touched by soft luxury as we transition into fall. Special touches like golden buttons or a belt will help brighten up your day when you can’t call it a day.

27 BLACK TURTLENECK WITH BLUE JEANS AND FLATS

Details make all the difference in giving a modern update to traditional prefall office styles. Look for metallic inserts on the shoes that provide an exceptional edge and a more fashion forward design.

CASUAL EARLY FALL WORK OUTFITS

For a hybrid office format that takes you from an early morning zoom meeting to your corner office later in the afternoon, you need options that go seamlessly from home to office and beyond.

28 RED BLOUSE WITH RAW DENIM JEANS AND SLINGBACKS

Pair your blue jeans with a red ruffled blouse for a chic, modern office look. Red blouses with ruffles and blue jeans are our favourite casual office choice this season.

CAPSULE EARLY FALL OUTFITS WITH PANTS

Beloved garments in new pairings will give your early fall work wardrobe a new lease of life. If you are looking for an understated approach, opt for classic shades of black and camel for timeless appeal.

29 CARDIGAN SET WITH BLACK VEGAN LEATHER PANTS AND POINTY FLATS

A chic knit set is the must-have item for early fall and will transition well into deep fall with a trench coat. You will love its versatility whether you pair it together or style the top and cardigan to create a variety of looks.

30 CABLE KNIT CAMEL SWEATER WITH SLACKS AND HIGH HEEL MULES

Camel for fall is a seasonal staple that never goes out of style. Wear it with black slacks and high heel mules that are great to take you from desk to dinner.

FAQ PRE FALL FASHION FOR WORK

Not sure what early fall work outfit to try first? Go through the FAQ. It might help. Also, check this article on Substack for size and fit of the garments featured.

MORE TRANSITIONAL BUSINESS OUTFITS FOR FALL 2025 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 and the most fashionable prefall fits.