8 CASUAL SUMMER TO FALL TRANSITIONAL OUTFITS TO WEAR NOW
HERE'S HOW TO TRANSITION YOUR FAVOURITE SUMMER CLOTHES INTO FALL
Casual September outfits that will transition well into October 2025. The best 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 2025 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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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 2025.
Well, if you managed to build a transitional capsule closet with summer clothes that are still in style for fall 2025 and with a few last seasons clothes that are coming back in fashion for fall 2025, then you have an easier job to do. You have all the clothes that can be worn when transitioning from summer to fall 2025.
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 the most fashionable casual summer to fall transitional outfits now – the best casual September outfits and easy to copy casual September outfit ideas!
THE BEST CASUAL EARLY FALL OUTFITS
By the way, all the collages below are hyperlinked and available for immediate purchase via links within the content itself. 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, scroll down to see how to wear a summer dress in fall 2025 casually.
STYLISH CASUAL SEPTEMBER LOOKS FOR A SPA DAY
But first, let’s check my easy early fall casual fits for the spa.
When comfort takes the spotlight, these outfits are your go-to indulgence. Bask in comfort, from head to toe if you are staying home, or choose the gentle caress of cotton that embraces your form if you are off to the spa.
1 LONG SLEEVE COTTON TEE WITH SWEATSHORTS AND ASCIS SNEAKERS
Maximum impact, minimum effort – update your casual September wardrobe with comfortable shorts and long sleeve T-shirts. Dressing down never looked so fabulous and comfortable.
As the early fall breeze begins to gently rustle the leaves, and the promise of a relaxing spa day beckons, it’s time to curate an outfit that strikes the perfect balance between ease and style. Try this: a black cotton long sleeve T-shirt paired with brick red H&M sweatshorts and the trendy Asics GEL-Kayano 14 “Simply Taupe” sneakers. This fit gives unparalleled comfort.
As you step into the tranquil oasis of the spa, the world outside seems to fade away, replaced by a serene and picturesque environment. The scenery at the spa is nothing short of enchanting, and every moment here feels like a beautiful escape.
The spa’s entrance welcomes you with a gentle, bubbling fountain surrounded by lush greenery. The sound of flowing water immediately soothes your senses as you make your way towards the locker rooms. The path is lined with fragrant blossoms, their delicate perfume filling the air and further enhancing the relaxation.
The black cotton long sleeve T-shirt is a versatile base for chic early fall looks. Its lightweight, breathable fabric ensures you stay cozy without feeling overheated on your way back home in the afternoon.
Pair it with the brick red H&M sweatshorts, adding a pop of color to your fit that beautifully complements the changing foliage of early fall. Crafted for comfort and style, these sweatshorts offer the perfect blend of relaxed fit and a flattering silhouette, making them ideal for a gym as well.
To complete the look, put on high socks and the Asics GEL-Kayano 14 “Simply Taupe” sneakers.
The Asics GEL-Kayano 14 “Simply Taupe” sneakers are a part of the renowned Kayano series, which has consistently delivered exceptional cushioning, support, and stability to athletes and chic girlies. In the case of the “Simply Taupe” colorway, fashion and function harmoniously come together.
The key feature that sets the GEL-Kayano 14 apart is its superior cushioning and support system. Asics’ signature GEL technology is strategically placed in both the forefoot and heel, ensuring that each step is cushioned, minimizing impact, and enhancing comfort. Additionally, the sneakers feature an integrated medial support system that helps maintain proper foot alignment, making them an excellent choice for those with overpronation or flat feet. Btw I love driving in these sneakers. Pov, I’m a speedster with a super heavy foot, but not entirely reckless, so I need to drive in shoes that allow me to modulate the pedals easier and prevent my foot from slipping off the brake.
Durability is another standout aspect of the GEL-Kayano 14. The sneakers are constructed with high-quality materials that can withstand the rigors of daily wear. Whether you’re hitting the pavement for a run, exploring the city on foot, or simply strolling through your favorite park before entering the spa (pov, that’s what I do every time), these sneakers are up to the task.
2 BLACK TANK TOP AND BLACK SKINNY PANTS WITH GAZELLE SNEAKERS
Your outfit choice plays a crucial role in setting the tone for a spa day. Select an outfit that is comfortable, effortless and chic! A black tank top, with black skinny pants, and digital lavender Adidas Gazelle sneakers, has been my latest fit.
Its wrinkle-resistant quality means you can carelessly toss it into the locker without worry, preserving its sleek appearance for when you return.
THE MOST FASHIONABLE CASUAL EARLY FALL OUTFITS FOR EVERYDAY
Infuse a burst of revitalizing energy into your everyday outfits with a fashionable top that promises to be the highlight of any occasion. My selection boasts a diverse array of casual styles designed to effortlessly transition you from day to night, easily paired with a casual jacket for added versatility.
3 SILK SLIP TOP WITH BLUE JEANS AND SNEAKERS
Whether you wear it when you meet your friends to hang out, or you save it for a casual date with your boyfriend, prepare to bask in the cascade of compliments when you wear this fashionable casual September outfit.
4 OVERSIZED DENIM JACKET WITH DARK JEANS AND FLAT MULES
While the urge to wear knitted fabrics when the sun hides under the clouds, and the temperatures drop is undeniable, we can’t stop bringing some denim into our casual early fall mix.
Oversized denim jackets are the perfect item to throw on when days start turning chilly. Paired with denim jeans, they will make a fashionable transition into your casual autumn wardrobe. Denim on denim has never looked so easy to wear.
5 JACKET WITH CARGO POCKETS AND BLACK LEGGINGS WITH SNEAKERS
Pov, this outfit is not with actual leggings. I don’t wear leggings, but I wear soft wool skinny pants that feel like leggings and look like pants instead.
The simplicity of this outfit cannot be overstated. Its clean lines and chic appeal make it a versatile choice for a relaxed day out.
Paired with Veja sneakers and red cardigan sweater (you can layer it up with a safari jacket if you are cold in the morning when you go for your coffee run), this outfit strikes a harmonious balance between casual and stylish. The cardigan sweater boasts a timeless design with a flattering, cropped fit that effortlessly complements your physique. The red hue exudes a sense of casual, while the dualwear (you can wear it as a cardigan or a sweater) ensure the cardigan to be your go-to staple for years to come.
CUTE CASUAL SEPTEMBER OUTFIT IDEAS
There can be something deeply alluring about a summer dress worn in fall. Paired with sneakers it is our French answer to September city casual. It’s just perfect for afternoon adventures in the city.
6 RED DRESS WITH SNEAKERS
Fashionable colour that really hits the mark, here is a playful option to liven up your day with your favourite summer dress.
7 SWEATER WITH LARGE FOLD AND WHITE LACE SKIRT WITH PUMAS
Revitalize your early fall ensemble with a trendy off-the-shoulder sweater featuring an oversized fold, perfectly paired with Puma sneakers. Whether you choose to combine them with a stylish white lace skirt featuring a daring slit or a sophisticated knee-length skirt, be prepared to bask in the cascade of compliments. POV, it’s clear – those sneakers are an absolute must-have for fall 2025.
8 DENIM ON DENIM WITH A DENIM JACKET AND LONG DENIM SKIRT WITH A SLIT AND SNEAKERS
Prepare for the brisk autumn air by pairing a cozy denim skirt with a matching denim jacket. This effortlessly chic combination guarantees a charmingly casual vibe as you stroll down the city streets.
FAQ CASUAL FOR EARLY FALL 2025
If you’re finding yourself inundated with a surplus of casual early fall outfit ideas, fret not. Simply sneak a brief glance at our FAQ section – it’s your reliable source for instant clarity and helpful guidance, without a shadow of a doubt.
Long sleeve cotton tee with sweatshorts and Ascis sneakers, black tank top and black skinny pants with Gazelle sneakers, slip top with blue jeans and sneakers, oversized denim jacket with dark jeans and sneakers, short red dress with sneakers, denim jacket with denim skirt and sneakers.
Early fall casual attire is a style of clothing typically worn during the transitional period between summer and autumn when the weather is beginning to cool down, but it’s not yet cold enough for heavy winter clothing. Early fall outfits often incorporate one lightweight layer that doesn’t need to be layered on. For example, you might wear a long sleeve T-shirt, or a light sweater. Casual pants like jeans, wool cady pants, cotton sweatshorts are popular choices for early fall because they provide warmth without being too heavy. You can also wear wool leggings at home. Footwear like sneakers, ballet flats, or loafers are often chosen for early fall outfits. They provide comfort and can be paired with both pants and sweatshorts.
Leggings, sweatshorts, sweatpants (unless you work from home, or are a professional athlete or P.E. teacher, of course), off the shoulder tops, sweater with large fold, fringed clothes, sandals, extra short shorts, extra mini skirts, extra short dresses, dresses and tops with a plunge, slip dresses, and swimwear as clothing are some of the biggest summer casual fashion trends that are not appropriate to wear for work. Point of view, the business dress code becomes more strict for businesswomen come September.
For businesswomen, early fall casual for work in September and October 2025 means fit and flare summer dresses with short sleeves and slingback pumps, short sleeve sweater with houndstooth pants and flat mules or loafers, striped cardigan with wide-leg pants and ballet flats, turtleneck top with dark denim jeans and flat mules, knit dress with loafers, short sleeve knit top with tweed shorts and slingbacks, turtleneck top with baggy pants and Pumas, cable knit sweater with midi pleated skirt and biker boots, double breasted blazer with blue jeans and kitten heel slingbacks, raffia tote bag or a hobo bag instead of the classic business tote.
Early fall casual for a wedding depends on the type of wedding. However, some of the typical early fall casual dresses for weddings are loose summer dresses with espadrilles, and long boho dresses with ballet flats. Well, truth be told, any wedding guest dress will become fall casual the moment you put on ballet flats or espadrilles.
A long boho dress with ballet flats, or a loose summer dresses with espadrilles (for a warm fall) will be the perfect choice for a casual ealry fall wedding.
Short dress with ballet flats or sneakers, a mini cotton dress with espadrilles, a wrap dress with flats, or ruffled dress with sneakers are some simple casual outfits for a casual party in early fall. Ps. Check the casual early fall outfits in this article for more inspiration.
September casual is a term used to describe a relaxed and comfortable style of clothing that is particularly suitable for the transitional period between summer and autumn. In many regions, September marks the beginning of cooler and more temperate weather, making it necessary to adjust one’s wardrobe accordingly. September weather can be quite variable, with warm days and cooler evenings. While layering is not a key feature of September casual wear, you might want to put a lightweight sweater on your shoulders.
October casual refers to a casual style of clothing that’s well-suited for cooler and more temperate weather. During this time, temperatures tend to cool down, and the landscape becomes rich with fall foliage. October casual attire is characterized by comfort, and warmth. Layering is a key feature of October casual wear. This might involve wearing a denim or a casual lightweight jacket over a T-shirt. October casual outfits often incorporate warmer fabrics like wool, denim, flannel, and heavier cotton blends. These materials provide insulation against the cooler weather.
Put on pointy ballet flats and hair accessories!
A cotton blouse/shirt and slacks with working boots for the countryside, and a cardigan over a striped shirt and wool pants with ballet flats or loafers for the city. Ps. See how to wear these old money casual September and October outfits in this article.
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.
