16 Stylish Early Fall Outfits You’ll Love for the Season

Amelia
Amelia 9 Min Read
Early Fall Outfit styled with a flowy white mini dress layered under a light denim shirt and finished with tan cowboy boots – perfect for sunny fall afternoons.

The awkward fashion limbo between summer and fall is real — when it’s 75 degrees one day and 60 the next. I spent way too much time overthinking my early fall outfits until Elizabeth reminded me that layering is everything. These 16 looks prove you can start embracing fall vibes without sweating through your cute sweaters.

1. The Double Denim Early Fall Classic

Early Fall Outfit featuring a classic double denim look with a dark blue jacket and jeans, styled with a white tee and burgundy boots – perfect for chilly cabin days.

@brookevestrand

This head-to-toe denim moment is why I love early fall outfits for women. The oversized denim jacket over straight-leg jeans creates that effortless cool-girl energy that works for everything from coffee dates to casual dinners. The rich indigo tones scream autumn without being too heavy for those warmer late summer early fall days.

2. Checkered Vest for Cute Early Fall Outfits

Early Fall Outfit with a black and white checkered sweater vest over a black mini skirt, paired with tall black boots and a quilted bag – cozy and chic for the season.

@natalie_kall

Elizabeth convinced me that vests are having a major moment, and she was absolutely right. This black and white checkered piece over a mini skirt gives serious academia vibes while staying breathable. Perfect for those early fall work outfits when the office AC is still blasting but you want to feel seasonal.

3. Oversized Denim + White Skirt Combo

Early Fall Outfit styled with a flowy white mini dress layered under a light denim shirt and finished with tan cowboy boots – perfect for sunny fall afternoons.

@a.n.honey

Sometimes the best late summer early fall outfits mix unexpected pieces. This oversized light-wash denim jacket over a flowy white mini creates the perfect balance of structure and femininity. The ankle boots add that fall touch without making you overheat during those 70-degree weather days.

4. Striped Shirt Early Fall Work Outfits

Early Fall Outfit mixing casual and tailored – oversized striped shirt with long denim Bermuda shorts and black Mary Jane flats for a relaxed city look.

@calliemarchant

When I’m overthinking my early fall work outfits, Elizabeth always suggests going back to basics. This oversized striped button-down over denim shorts proves that sometimes simple wins. The relaxed fit keeps you comfortable while looking polished enough for casual Fridays or weekend brunches.

5. Cable Knit for Cozy Early Fall Outfits

Early Fall Outfit with a cozy beige knit sweater layered over denim shorts, paired with white sneakers and a red shoulder bag – ideal for lakefront walks.

@brookevestrand

This oversized cable knit sweater gives me all the fall feelings without being too heavy for transitional weather. The cream color feels fresh for late summer outfits early fall, and layering it over denim shorts creates that perfect high-low mix that defines early fall casual outfits.

6. Ribbed Dress for Cute Early Fall Outfits

Early Fall Outfit in a cute strapless striped knit dress, styled with minimal accessories and black slip-on shoes – great for soaking in the last warm days.

@maddybajczyk

Elizabeth spotted this striped ribbed dress trend before anyone else. The fitted silhouette and warm tones make it ideal for early fall family photo outfits or date nights. The midi length works perfectly for that in-between weather when you want coverage but still need breathability.

7. Printed Jacket Statement Look

Early Fall Outfit featuring a black mini dress and a floral denim cropped jacket, styled with loafers and white socks – an edgy and fresh transitional look.

@_melisoto

This floral denim jacket proves that early fall outfits don’t have to be boring. The blue and white print feels fresh while the denim weight is perfect for layering. Elizabeth said it gives “vintage but make it modern” vibes — exactly what I was going for in my casual early fall outfits.

8. Striped Shirt + Distressed Denim

Early Fall Outfit with a sporty-casual vibe – ripped mom jeans, white crop top, and a maroon striped baseball shirt, paired with black-and-white sneakers.

@natalie_kall

Sometimes the best early fall outfits men and women can both appreciate are the effortlessly cool ones. This burgundy striped button-down over distressed jeans hits that sweet spot between polished and relaxed. The rich color palette screams fall without being too heavy for warmer days.

9. All-White Early Fall Work Outfits

Early Fall Outfit in crisp white – sleeveless button-down top and midi skirt, accessorized with a structured straw bag and white sandals for a clean, fresh look.

@haleyvbrown

I was hesitant about white after Labor Day until Elizabeth reminded me that rules are meant to be broken. This crisp white button-down dress is perfect for those early fall work outfits when you want to look put-together but the weather is still unpredictable. The structured silhouette works for professional settings.

10. Western-Inspired Early Fall Outfits

Early Fall Outfit with a warm-toned sweater dress cinched with a statement belt, paired with cream-colored fringe knee-high boots – perfect for seasonal outings.

@reeseybsboutique

This brown coordinated set with that statement concho belt gives major western princess energy. Elizabeth said the fringe boots make it Instagram-ready, and she wasn’t wrong. The earthy tones are perfect for early fall casual outfits, especially for outdoor events or festivals.

11. Trench Coat Sophistication

Early Fall Outfit with a chic monochrome set – a beige crop top and matching high-slit midi skirt, layered with a cropped trench jacket for a stylish and cozy vibe.

@heyitsnatalie

When you need early fall outfits that transition from day to night, this cropped trench over a neutral midi is perfection. The classic silhouette feels timeless while the nude tones work beautifully for those warmer fall days when heavy coats are still too much.

12. Pink Ruffle Femininity

Early Fall Outfit featuring a cozy beige sweater tucked into a pink ruffled floral midi skirt, paired with tall white cowboy boots for a soft and feminine seasonal look.

@laura.marie.xo

Elizabeth convinced me to try this pink polka dot ruffle skirt, and I’m so glad she did. Paired with a neutral sweater, it creates one of those cute early fall outfits that feels romantic and seasonal. The midi length with boots gives that perfect fall transition vibe.

13. All-White Pleated Elegance

Early Fall Outfit in elegant neutrals – a pleated white midi skirt with a matching knit top and cropped jacket, styled with taupe boots for a refined city look.

@rebekabarath

This white pleated set proves that late summer early fall outfits can be sophisticated and breathable. The matching jacket and skirt create a cohesive look that works for everything from brunch to evening events. Elizabeth said the texture keeps it interesting — she was right as always.

14. Off-Shoulder Knit Set

Early Fall Outfit in a cozy two-piece ribbed knit set – off-shoulder grey sweater and matching mini skirt, accessorized with a headband for a cute, snug aesthetic.

@shop.baileyrose

When I’m putting together cute early fall outfits, this grey knit matching set always wins. The off-shoulder top feels flirty while the mini skirt keeps things young and fresh. Perfect for those early fall family photo outfits when you want to look coordinated but not overdressed.

15. Denim Corset Chic

Early Fall Outfit with an urban edge – strapless denim bustier paired with black wide-leg pants and slip-on sandals, finished with a minimalist white shoulder bag.

@esleddy

This light-wash denim corset over wide-leg black pants creates one of those effortlessly cool early fall casual outfits. Elizabeth said the strapless top keeps it summer-appropriate while the styling feels distinctly fall. The contrast between fitted and flowy is what makes this work.

16. Corduroy Jacket Perfection

Early Fall Outfit in warm tones – a plaid mini skirt, white top, and brown corduroy jacket styled with white cowboy boots and a latte in hand for a perfect fall café run.

@laura.marie.xo

Nothing says early fall outfits like corduroy, and this brown jacket over a plaid mini hits all the right notes. The rich textures and warm tones create that perfect autumn mood without being too heavy for transitional weather. Elizabeth called it “cottagecore meets city girl” — exactly the vibe I was after.

FAQs About Early Fall Outfits

What month can I start wearing fall clothes? September is typically when you can start incorporating fall pieces, but it really depends on your climate. I usually start mixing in light jackets and boots when temperatures consistently hit the 60-70 degree range.

What to wear in 70 degree weather in the fall? Layering is key! Think light sweaters, denim jackets, or cardigans that you can remove if it warms up. Jeans with ankle boots or sneakers work perfectly for this temperature.

What is proper fall attire? Fall attire typically includes layers, richer colors like burgundy and brown, and transitional pieces like light jackets, boots, and scarves. The key is being prepared for temperature changes throughout the day.

Can I wear jeans in the fall? Absolutely! Jeans are a fall staple. From straight-leg to wide-leg styles, denim works perfectly for early fall outfits and can be dressed up or down depending on what you pair them with.

Whether you’re putting together early fall work outfits or planning cute early fall outfits for the weekend, remember that confidence is your best accessory. Save your fave looks and don’t forget — when in doubt, add a layer you can easily remove!

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