5 Styling Tricks To Take Your Summer Outfits Into Fall

5 Styling Tricks To Take Your Summer Outfits Into Fall

One of the most common questions my readers had for me over on Instagram Stories was how to transition summer outfits or pieces into fall. There’s always that weird time of the season where you’re kind of in limbo. It’s warm, but it’s also cool in the mornings and night. The calendar says October, but you’re still wanting to wear summer favorites but not sure how to. It can be a hard time of year to navigate your closet and I’m right there with you.

I find this to be the absolute hardest time to dress for myself too gals. Especially since I’m so hot-blooded and end up wanting to rip off any layers the second I get outside. But here’s the thing, you can’t just run around in October in a white eyelet dress. Remember this post?

There are rules to transitioning from season to season and today I’m sharing 5 really easy styling tricks that will help you get through this weird time period of warm weather yet you’re craving all things fall.

PS check out this post for even more inspiration for dressing when it’s hot out in the fall!

5 Styling Tricks To Take Your Summer Outfits Into Fall

Choose Black Leather & A Great Bootie

My favorite trick in the book, swap sandals for booties and add a leather jacket. This is a great in-between look to get you ready for fall. Depending on your office, you could easily add a black blazer and black pump to make a great black and white look. You saw this look last week and it’s a tried and true favorite. This is a great way to still have bare legs when the temperatures are still in the 70s.

Original post here and here.

get the look

Go For Long Sleeves, Booties & Fall Hues

A denim skirt has to be one of my favorite pieces in my closet. You can’t wear this into the winter unless you add tights, but for fall it’s great. I personally always gravitate towards a denim mini for those warm fall days that linger here in the South. To take a denim mini from summer to fall, just swap your colorful sandals and tee for a ribbed sweater and booties. This would also be perfect with some OTK boots as well and a big cozy scarf for extra warmth once the weather really cools off. But this lightened up version is great for hot fall days and feels seasonally appropriate.

Original post here.

get the look

Just Add Suede & Toss The Summer Accessories

This dress has to be one of the easiest to transition from not only season to season, but work week to weekend. To take it from summer with sandals and a straw hat to fall, all you need is a great jacket and swap your shoes. This look will also be perfect with some booties. Getting rid of any and all summer accessories is a must to transition the right way. Straw hats, summer bags and sandals should all be getting tucked away until spring. You’ll feel instantly inspired for the season once you get rid of those pieces and are forced to grab your leather and suede instead.

For the office, add a crisp blazer and a nude pump. I love adding the belt, but it’s great just as is.  You could even do this with a nude loafer for a more preppy and classic look. If you haven’t picked up this dress I can’t recommend it enough. I’ll be applying style tip #1 soon and plan to wear this with black booties and my go-to leather jacket soon.

Original post here and here.

get the look

Add A Cozy Knit Cardigan & Loafers

A tried and true fall favorite combo, cozy oversized cardigan with loafers. It’s the ultimate Grandpa style hack and I totally love it. Adding a knit cardigan over just about any of your summer dresses will help transition them easily. You can also add one of these cozy cardigans over your favorite tank and jeans like I’ve done here. It screams fall and adds not only texture but warmth.

get the look

The 9-5 Trick With A Boyfriend Blazer and Loafers

One of my favorite tops from this past summer was my ruffle eyelet top from Madewell. I’m not ready to give it up just yet so I’m transitioning this look from summer to fall with a few fall favorites great for the office. My boyfriend blazer and suede blush loafers. You barely notice that I’m in a summer top once you add on the layers and tuck it into some high waisted jeans.  If you have a favorite summer top, try layering it under a crisp boyfriend blazer or a tweed one. And always be sure to swap your shoes out for something more fall appropriate!

Original post here and here.

get the look

All photos by Hannah Michelle

Jessica is an Atlanta life and style blogger. Aiming to bring practical tips to your every day life. Tips that you can easily tackle and make your life feel just a tad more 'put-together'.

Leave a Comment


  1. 9.19.18
    Laura Leigh said:

    Might be my favorite post of yours ever! Absolutely love this Jess. And honestly can’t pick a favorite look! They’re all so good!

    xo Laura Leigh
    Louella Reese

  2. 9.19.18

    The bow on that skirt gets me every time! I love it. Pairing a leather jacket and booties with a dress is my fave.

    • 9.19.18
      Jessica said:

      The bow is the best, I’m in love with it. Such a great buy!

  3. 9.19.18

    Love these tips!! This is something I DEFINITELY need help with!! Can’t wait for fall, but also love my sundresses!

    xo, Hillary | hillheady.com

  4. 9.19.18
    Sherri said:

    Okay, YES to the hardest season to dress for! And that cardigan/loafers combo is giving me TONS of ideas! Great post, lady.

    • 9.19.18
      Jessica said:

      It’s not usually my go to so I put it in there to remind myself. Then I bought 3 damn cardigans today ?

  5. 9.19.18
    Kara said:

    You make dressing for fall so effortless!! Also love the suede jacket tip!


    • 9.19.18
      Jessica said:

      Thanks! The suede jacket trick is probably my laziest and easiest!

  6. 9.19.18
    Megan said:

    Love this post! The fall booties you feature are super cute!

  7. 10.14.19
    Rachel said:

    Okay, I need all of these outfits stat! They’re all so cute for summer and fall.


  8. 10.14.19
    Mariah said:

    The denim skirt transition is my favorite! I love changing out tanks for sweaters.


    • 10.14.19
      Jessica said:

      Always! And I sometimes keep the tank on underneath in case I get hot, ha

  9. 11.4.19

    You shared some great styling tips! Of course, a great ankle bootie can really do wonders for a simple dress and jacket combo!

    XO Amanda || Affordable by Amanda

    • 11.4.19
      Jessica said:

      It’s the easiest trick for sure!

  10. 11.15.19
    Awesome said:

    These street style fashion looks are great for summer, but what about winter ideas?

    • 11.15.19
      Jessica said:

      I wouldn’t recommend wearing summer pieces in the winter. Summer to fall is a more natural transition with your closet. For winter outfit ideas click STYLE in the top navigation and then fall & winter

  11. 12.4.19

    Thanks for sharing these beautiful outfits! I love look with pink dress.