Transitioning Your Shorts for Fall

high waisted shorts styled for fall

Summer might be unofficially over, but the temps are still warm here during the days so I’m not *quite* ready to put my favorite summer dresses, shorts, and houses away just yet! The mornings and evenings have definitely cooled down quite a bit but it gets warm in the afternoons, so I’m all about the layers and one of the easiest ways (IMO) to dress for this time of year is to style my favorite shorts with some sort of layer. 

Enter: my favorite sweater blazer. I will probably only be able to get another week or two out of this effortless look, but depending on where you live, you might be able to squeeze a little more time out of it!

More Ways to Style Your Shorts for Fall

With a Denim Jacket

Denim jackets are a wardrobe staple and can essentially be worn year round (depending on where you live!). I love that they are so effortless and easy to pair with pants, dresses, skirts, and you guessed it – shorts!

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With a Structured Blazer

A great blazer is such an easy way to elevate any outfit, and when paired with shorts, you instantly have a great outfit for drinks with the girls.

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With an Anorak

Fall in New England always brings unpredictable weather, making an anorak jacket your new best friend. They’re light weight and packable but also give you the protection you need from the chilly wind and rainy weather. Even when it’s humid and you want to have bare legs.

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With a Lightweight Sweater

I always say I wish I lived in a place that it was 70° out year round so I could have the choice of wearing jeans and a t-shirt or shorts and a lightweight sweater. And cmon, this combo is perfect for any weather between summer and fall that mother nature might throw our way.

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With a Leather Jacket

Give your shorts an edgy “I don’t give a fuck” vibe by pairing them with your favorite leather jacket. By opting for a neutral color (white, oatmeal, blush) instead of the classic black, your outfit will still feel summer-y and day time appropriate.

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What are your favorite ways to style your shorts for fall?

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Free People Rib Brami Top / J. Crew Sophie Open-Front Sweater Blazer / AGOLDE Dee Ultra High Rise Short / Seychelles Total Relaxation Slide Sandal / Everlane The Day Mini Tote / Daniel Wellington Mesh Strap Watch / Ray-Ban Original Aviators

Photography By Caroline The Photographer

Leave a Reply


  1. 9.16.20
    Lizzie said:

    These are all such fun ways to transition shorts into cooler weather! Love the way you styled it as well as the sweater/shorts combo!


  2. 9.16.20
    Anna English said:

    I definitely find myself still wearing my favorite denim shorts during fall months! Houston is so hot up until Nov/ Dec!

  3. 9.16.20
    Rach said:

    I’m loving the layering with blazer and denim shorts. Btw, your shorts are so cute!

  4. 9.16.20
    Kim said:

    It’s so hot here in Houston, that the shorts looks are my kinda fall outfit! Great inspiration for me!


  5. 9.16.20

    It is not even fall yet, and the temperatures were in 40s this morning. I am hoping to still get some wear out of my shorts. Keeping my fingers crossed.


  6. 9.16.20
    GRETA said:

    I love all the way to transition these shorts for fall! So many fun looks.

  7. 9.17.20

    Coming from Long Island it’s such a thing to wear sweaters with shorts as the weather starts to cool. Great tips! xoxo, Sarah

  8. 9.17.20
    Stephanie said:

    I’m such a coward when it comes to shorts. I just really don’t like them on myself, and this year I never got a single bit of sun, so I’m totally vampiric. Showing off a ton of leg is not my cup of tea right now haha. Unless I have time for a faux tan .. then I may still pull out my paperbag shorts. But for now, gimme ALL the autumn outfits haha!

  9. 9.17.20
    Stephanie said:

    I accidentally hit “submit” before I finished my comment. I was going to say that I do LOVE how you styled shorts here though. That sweater blazer is gorgeous. And I admire the other stylings as well. They’re so cute!

  10. 9.17.20
    Emely said:

    I love the idea of pair a blazer with shorts. So chic. I haven’t worn jean shorts or actually jeans at all this year lol but will definitely try this look out once I do.

  11. 9.17.20
    Lily said:

    I love all of these looks. And I love that your shorts aren’t short…that’s hard to find now-a-days!

  12. 9.21.20
    Annie said:

    I LOVE all of these different looks! Thanks so much for sharing such great fall outfit inspiration!