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 2023 – 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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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 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 2023.
Nevertheless, some late summer work outfits smell a lot of autumn already. Well, I can’t help myself not to start wearing fall winter 2023/24 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 PRE FALL WORK OUTFITS 2023
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 2023!
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.
FASHIONABLE BUSINESS FORMAL 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 formal early fall work outfits that are equally hard-working.
1 BLACK TURTLENECK SWEATER WITH PUDDLE PANTS AND STILETTOS
Return to the office looking the most fashionable yet. Nail the clean girl aesthetic in a fashionable black turtleneck sweater and puddle pants.
Your reflection in the mirror whispers confidence, and as you leave home in your meticulously curated Max Mara black 3/4 sleeve turtleneck virgin wool top, black Sézane Yves trousers, and Casadei blade pumps outfit, a whirlwind of emotions dances within you.
Stepping out of your front door, you feel a sense of exhilaration and excitement, as if going to work for the first time. The world outside may be bustling with the usual commotion, but your outfit exudes an air of quiet luxury and sophistication, commanding attention without a word.
As you make your way to work, the black turtleneck envelops you in warmth and comfort, a cozy embrace against the early autumn chill. Its three-quarter sleeves hint at the season’s change, promising days of pumpkin-spiced lattes and falling leaves.
The Sézane Yves trousers are a revelation in themselves—tailored to perfection, they elongate your legs and provide a powerful silhouette. Their black hue effortlessly complements the turtleneck, creating a seamless fit that speaks of professionalism and style. You feel like you can conquer the world, one confident step at a time.
And then, the pièce de résistance – those Casadei blade pumps in pink. Pov mine are in lavender pink, but you might prefer a rusty pink. They’re the pop of color that elevates your outfit from ordinary to extraordinary. Pov if you can 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-split 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 the &OtherStories red ruffle silk blouse. The vibrant red hue not only brightens up your outfit but also your entire day. It’s a color that exudes power, passion, and a touch of daring sophistication. And it’s the colour of the season.
Correspondingly, the ruffled details add a playful yet professional touch, showing 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, not just 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 brown.
3 RELAXED PANTSUIT WITH MARY JANES WITH MULTIPLE STRAPS
Precisely executed, traditional tailoring gets a relaxed update this season. Completely reimagined with low waist puddle pants or a 80s style blazers, it is high time to wear a suit.
Ps. Since I hate the 80s, I made sure to add a blazer that is trendy, but doesn’t look like it was dragged from the 80s.
4 LEOPARD PANTS WITH A NAVY BLAZER AND BLACK BLOUSE
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 navy blazer and black blouse.
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 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 PUMPS
A black pantsuit with a sleek black blazer and chic pants will give you infinite style options worn together or separately with a camel sweater or layered over/under your favourite summer dress.
Venture beyond the realm of co-ord sets; this season, easy separates take center stage. Picture, a pair of rich brown trousers, akin to the luxurious brown Max Mara trousers that have become my style staple. They effortlessly pair with a simple tank top and a commanding black double-breasted blazer. Btw mine is from Pinko.
These pairings aren’t just about comfort—they channel confidence, a must-have attribute in any workplace setting.
To finish this business (semi)formal outfit, set your sights on none other than the legendary Valentino Garavani Rockstud kitten heels. These shoes, both chic and comfortable, achieve an exquisite equilibrium between comfort and sophistication. The kitten heel’s modest elevation ensures effortless movement, while the unmistakable Rockstud embellishments impart a dash of opulence and individuality to your overall look. You can depend on them to be the most comfortingly stylish office shoes during this transitional season and beyond.
8 AUTUMN PANTSUIT WITH 80s STTLE 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.
CUTE EARLY FALL WORK OUTFITS THAT MEET BUSINESS CASUAL 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 2023.
9 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.
10 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. Its gentle embrace 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. Btw stripes are in fashion for fall 2023.
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. These wide-leg wonders are not only comfortable but also incredibly flattering. They elongate your legs and provide a graceful silhouette that complements the cardigan and shirt combo beautifully.
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.
Complete your look with a headband. This small 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.
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.
11 TURTLENECK SWEATER WITH DARK DENIM AND HEELED LOAFERS
Whether it is casual at home or dressed up for the corner office, a black turtleneck sweater 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.
12 SHORT SLEEVE KNIT DRESS WITH HEELS AND A SUMMER BAG
Navy short sleeve dresses are the easiest outfit to put together if you are rushed for time. Just step into some heels 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.
13 RED DRESS WITH HEELS AND HAIR ACCESSORIES
Warm up your fall work wardrobe with rich reds and deep burgundies. Red 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 Fiery Red and Radiant Red that sit well alongside fall staples of brown and black for look that work in perfect harmony.
14 BLAZER ON SUMMER WORK DRESS WITH SLINGBACKS
Rewear your favourite summer dress with a dapper black blazer and chic slingbacks.
15 KNIT DRESS WITH LOAFERS
It is time to start thinking about cool weather dressing, and we are enamoured with chunky sets in minimalist block shades. Soft cardigans and knitted dresses 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.
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 add an extra dimension with boucle fabrics shot through with metallic threads that glint when they catch the light.
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 or long in order to be suitable for work in early fall. In fact, extra details like pockets and metallic braid give additional possibilities to make the transition from corporate daytime to a formal evening. Treat yourself to tweed shorts to add little luxurious touches that will lift the spirits on foggy mornings.
Try tweed shorts with a short sleeve sweater and kitten heels. A short sleeve sweater with an ornate finish around the neck (see the product gallery below) is a great way to add interest to your outfit. Look for turtlenecks 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?
17 TURTLENECK WITH WIDE LEG PANTS AND KITTEN HEELS
Buy into our favourite trouser trend and get wide leg pants. Style them with a halterneck top to give an added kick or indulge in some retro nostalgia with camel and black.
When it comes to the colour of the season, there is nothing better than digital lavender. Either in glossy or something more tangible, try digital lavender Adidas gazelle sneakers that are the best shoes to wear with puddle pants when you are looking for a sleek put-together silhouette within business casual code.
For the silhouette, we love the low waist for a slightly more boyish fit. Pov the pants linked in the collage and product gallery stay low on my hips. But you might need to size up for the same effect.
19 TURTLENECK TOP WITH TROUSERS AND KITTEN HEELS
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 2023 TRANSITIONAL BUSINESS OUTFITS WITH A SKIRT
Summer may be drawing to a close, but skirt season is far from over. All in all, a new skirt always gets us in the mood for work.
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 silk 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 atmosphere.
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 the most fashionable skirt for the foreseeable future. It is the key trend for fall winter 2023/24 and SS24 and will offer you the perfect balance between looking professional and feeling special.
Finish with black slingback pumps with kitten heels. The black hue provides a chic contrast to the pristine white T-shirt and adds a touch of drama to your outfit. The kitten heels will ensure comfort and flexibility, allowing you to move seamlessly through your afternoon meetings and tasks.
POV This September 2023 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.
21 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.
22 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 lends an air of professionalism to your outfit, while the deep navy hue adds a touch of classic elegance.
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.
23 OVERSIZED DOUBLE BREASTED BLAZER WITH NAVY JEANS AND PUMPS
Embrace the fun of wearing jeans for the office and get ready for work in an oversized blazer and heels.
24 POLKA DOT BLOUSE AND BARREL JEANS WITH MESH BALLET FLATS
A striking bow is the only adornment you need for an early fall work outfit with jeans that never feels overwrought.
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.
25 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.
26 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.
27 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.
28 OVERSIZED BLAZER WITH BLUE JEANS AND SNEAKERS
Blue jeans and oversized blazers are perfectly suited for busy days. Pair with chic sneakers if you need to go places.
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.
Dressing up for work at the end of summer requires finding the right balance between staying cool and comfortable in the lingering warmth while maintaining a professional and polished appearance. Start with a lightweight base layer, such as a blouse or a button-down shirt. Opt for breathable fabrics like cotton or silk to combat the lingering late summer heat. Transition your wardrobe by incorporating early fall pieces like blazers, cardigans, or lightweight sweaters. These can be added or removed depending on the temperature. Dresses can still be worn in September. Choose ones with sleeves or layer on a blazer. A tailored blazer is a versatile and timeless piece for September. Navy, gray, or black work well. It instantly elevates your look and provides warmth when needed. Stick with fashionable bottoms like low waist trousers, or pencil skirts. Neutral colors such as black, navy, or gray are always office-appropriate. Closed-toe shoes are a must as temperatures drop. Consider loafers, ballet flats, or kitten heel pumps for comfort and style. Slingbacks and mules are an option, too.
The best back to work outfit for teachers in primary school is an early fall outfit in bright colours that make kids feel welcome back to school. Browse through the early fall work outfit ideas in this article to find the best early fall teacher outfit for you.
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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.