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Fall/ Winter Fashion, Outfits · July 29, 2024

15 Stylish and Easy Transitional Outfits from Summer to Fall

It’s that perfect time of year, between summer and fall, when the crisp autumn air start to sweep in. However, choosing what to wear during this transitional weather can be tricky, but don’t worry! In this article, we’ll dive into the must have items you need to create easy and stylish Transitional Summer to Fall Outfits.

Transitional Outfits from Summer to Fall


So, if you’re not quite ready to bid farewell to your beloved linen and crochet pieces, you can still rock your summer staples with a bit of clever layering. By pairing your lightweight summer items with cozy cardigans, denim jackets, or stylish blazers, you can seamlessly transition your look into the cooler months.

On the flip side, if you’re feeling tired of your summer wardrobe and eager to dive into fall fashion, now is the perfect time to start incorporating those autumnal colors and textures into your outfits.



Essential Pieces for Transitional Outfits

Transitioning your wardrobe from summer to fall is all about choosing the right pieces that will help you seamlessly blend your summer staples with cozy fall favorites. this can be done with the following key pieces:

  1. Denim Jacket
    A denim jacket is a versatile layering piece that adds the right amount of warmth without making you overheat and can be layered over your favorite summer pieces like a dress or a mini skirt.

  2. Cardigans and Sweaters
    • Lightweight sweaters and cardigans are perfect for layering over a sundress or pair with jeans and a tee. They add coziness without being too heavy, making them ideal for those early fall days.

  3. Ankle Boots 
    • The easiest way to start transitioning into fall dressing is by swapping sandals for ankle boots or cowboy boots. Ankle boots are a fall staple that pairs well with jeans, dresses, and skirts. They offer both style and comfort, making them perfect for the transitional season

  4. Trench coat
    • A trench coat is a fall wardrobe staple, it provides warmth but also looks very stylish layered over any basic outfit. You can wear the cropped version if you feel like the temperature is still high to get that look without the added heat.
  5. Blazer
    • A blazer is a versatile piece that can elevate any outfit. Wear it over high-waisted shorts, jeans, or dresses for a put together look that’s perfect for early fall.
  6. Leather Jacket
    • Leather jackets add an edgy touch to any outfit and is the perfect layering piece as temperatures drop. It pairs well with miniskirts, jeans, or dresses, making it a must-have for fall.
  7. Layering Tops
    Swap your tank tops and crop tops to long sleeve tops that can be layered under jackets or even dresses.  Long-sleeved tops are versatile and can be easily mixed and matched to create endless outfits. 

  8. Midi and Maxi Skirts
    • Midi and maxi skirts can be easily transitioned from summer to fall. Pair a denim or satin skirt with a sweater or blazer for a chic fall outfit


Transitional Summer to Fall Outfits 

1. Leather Jacket, Dress & Booties

This is the ultimate early fall outfit; it allows you to keep the summer vibes while adding warmth for the cooler fall weather​ Throw a leather jacket over a floral mini dress and finish the look with a pair of black ankle boots for a chic look.

transitional outfits summer to fall

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2. Trench Coat & Denim

Pair your jeans with a t-shirt and layer a trench coat over it. Add ankle boots or flat ballet flats for a sophisticated yet casual outfit.

A cropped trench coat is perfect for this time of year, as it allows you to start experimenting with those fall wardrobe staples without feeling overheated.

transitional outfits summer to fall
@freyakillin

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3. Satin Skirt & Sweater

Layer a cozy sweater over a satin skirt and pair with cowboy boots or ballet flats. This mix of textures and styles makes for an interesting and classy outfit​.

@jasmineslh

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4. Sweater Over Your Shoulders

Tie a light sweater over your shoulder and pair it with a basic outfit like black trousers and a white shirt. This look is timeless and perfect for those unpredictable fall days. This outfit can be dressed up with a pair of heels or dressed down with loafers or ankle boots.

transitional outfit idea
@rebekabarath

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5. Plaid Shacket & Jeans

A plaid shacket worn over a pair of denim pants and a basic top creates a stylish yet casual fall outfit. Complete the look with loafers or ballet flats.

transitional outfits summer to fall, shacket
@cocobeautea

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6. Cardigan & Jeans

Combine an oversized sweater with a pair of jeans and chunky trainers. This outfit is the perfect balance between summer and fall capsule wardrobe pieces.

transitional outfits summer to fall, cardigan
@itsyuyan

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7. Blazer & Denim Shorts

The blazer and shorts combo never fails! Pair a tailored blazer with high-waisted shorts and a t-shirt. Complete the look with white trainers or cowboy boots for a versatile transitional outfit suitable for both warm and cooler days.

transitional outfits summer to fall, blazer, denim shorts
@mervesadol

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8. Tweed Jacket & Wide leg Trousers

Nothing makes me more excited for fall than the thought of wearing tweed. It just instantly elevates any outfit no matter how basic. Layer a tweed jacket over blouse and wide leg trousers. Pair with boots or low-heeled pumps.

transitional outfits summer to fall, tweed jacket
@karinastylediaries

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9. Maxi Denim Skirt & Blazer

Combine a tailored blazer with a midi denim skirt and a white tee. Finish the look with knee-high boots or trainers for the perfect transitional outfit.

transitional outfits summer to fall, denim skirt

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10. Preppy Vibes

How cute is this outfit for early fall? Start with a button-down shirt under a sweatshirt and pair them with a mini skirt and loafers.

transitional outfits summer to fall, preppy outfit

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FARAH salem

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11. Denim Jacket & Hoodie

We can’t talk about transitional outfits without mentioning denim jackets. This is such a versatile piece that you can layer over any basic outfit. Pair it with a basic hoodie and pair of jeans for a casual outfit.

transitional outfits summer to fall, denim jacket
@freyakillin

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12. Leather Jacket & Mini Skirt

Another leather jacket and ankle boots outfit combination. This time its paired with a mini skirt and a basic white t-shirt. This edgy outfit is perfect for a night out or a stylish day in the city. Opt for a colored leather jacket in autumnal shades for a fun and cozy look.

transitional outfits summer to fall
@yaroslava_mayorova

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13. Tailored Blazer & Jeans

This outfit combination is both timeless and practical. Pair a basic t-shirt with your favorite pair of denim pants and layer a tailored blazer over it. Finish the look with a pair of loafers or ballet flats for a casual chic outfit.

transitional outfits summer to fall, denim, blazer
@cocobeautea

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14. Denim Skirt & Hoodie

This is one of my favorite transitional outfit ideas. It’s such a comfy and cool outfit that is perfect to transition from summer to fall. Pair a lightweight hoodie or sweatshirt with a maxi denim skirt and finish the look with a pair of chunky trainers.

transitional outfits summer to fall, hoodie, denim skirt
@tessavmontfoort

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15. Bomber Jacket & Wide leg Trousers

A classic bomber jacket over a graphic tee with wide leg trousers and heeled trainers creates a sporty and stylish outfit that is perfect for early fall.

transitional outfits summer to fall, leather jacket
@indiaamoon

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Tips For Creating Transitional Looks

  • Outfit Formula: Start with a light base outfit from your summer wardrobe and add layering pieces like cardigans and jackets. This formula ensures you stay cool if the temperatures rise while still having those extra layers when the weather changes.

  • Mix Textures: Experiment with different fabrics like denim, leather, silk, and knitwear to add interest to your outfits this fall season.

  • Color Palette: Transition from summer to fall by incorporating muted, earth-tone colors as well as darker colors like black, tan, and jewel tones that are perfect for the new season.


  • Accessorize Smartly: Incorporate fall accessories like hats, scarves, and statement belts to elevate your look.

With these essential pieces and outfit ideas, you’ll be ready to create Transitional Summer to Fall Outfits ensuring that you look fabulous no matter what else is going on. Remember, the key is to layer smartly and mix and match items from your summer wardrobe with fall staples for a seamless transition.

Posted By: Farah Salem · In: Fall/ Winter Fashion, Outfits

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