30 Transitional Fall Styles

Happy Friday, friends, and cheers to the weekend! I have a hot date with the couch and my new foot pillow, ha! And I never thought I’d see the day (in this decade anyway), but I’m the proud new owner of this. I will say, it’s made getting around easier.

Today is a good day though, because Mama Sugarplum is coming! She’s going to help me out with a few things around the house, and I’m hoping to get her to try on some darling new arrivals that I ordered! I’m sure I’ll share some fun over on my Instagram Story HERE.

Okay, moving on to the post… today we’re talking transitional Fall styles. Summer may be my favorite season, but this is about the time when we start dreaming of pumpkin candles and changing leaves! But it always takes me a bit to remember how to transition to a new season. It’s like I completely forget how to get dressed!

My go-to formula for dressing in transitional seasons is to cover either my arms or my legs… that way I’m straddling the heat of summer and the chill of fall. Or at the very least, staying a little more true to the calendar.

And of course it wouldn’t be transitional season without a jean jacket, so be prepared to wear it on repeat! I have several in my closet, but this one is a favorite, and finally back in stock! (And 15% off with code CASSIE15)

Here are 30 styles to inspire you for the new season… whether you’re working from home, the classroom, the office… there’s a little something for everyone!

Spotty Drop Waist Dress (Leopard Coffee, Small)
Similar Ankle Booties (TTS) | Saddle Bag | Removable Strap (Stripe Rose Brown) | Layered Initial Necklace | Gold Bead Bracelets | Medium Hoop Earrings

Tie Waist Dress (Red, Small)
LeftBraided Heels (Look For Less HERE) // RightJean Jacket | Similar Ankle Booties (TTS) | Panama Hat

Floral Maxi Skirt (Yellow, Small)
Sweater Tank (Khaki [No Coffee], Small) (20% off!) | Cut-Out Sandals 

Tie Waist Chiffon Dress (Flower Black, Small) | Tie Waist Flowy Dress (Red, Small)
LeftStrappy Heels (size up half) | Gold Bead Bracelets // RightBlock Heel Booties (Nude, TTS)

Decked Out Day Dress (XXS) (code SUGARPLUM10)
Similar Ankle Booties (TTS) | Crossbody Bag | Striped Removable Strap (Gold Buckle-24)

Notch Collar Blazer (XS) (code SUGARPLUM10)
Pocket Tee (Small) | Raw Hem Crop Jeans (Size 2) | Rothy’s Sneakers
Right: Similar Racerback Tank | Light Wash Risen Jeans (code SUGARPLUM10) Similar Loafers

Utility Jumpsuit (Army Green, Small)
Similar Ankle Booties (TTS) | Saddle Bag | Removable Strap (Stripe Rose Brown) | Layered Initial Necklace | Gold Bead Bracelets | Medium Hoop Earrings

Half Zip Collar Sweater (Khaki, Small) | Wide Collar Sweater (C Striped Khaki 2, Small)
LeftSimilar Crop Jeans (Size 2) | Veja Sneakers | Gold Bead Bracelets
RightFaux Leather Leggings (Small) | Chain Slide Mules (on sale!)

Open Pocket Cardigan (Solid Beige, Small)
LeftPocket Tee (Small) | Similar White Jeans | Cut-Out Sandals | Layered Initial Necklace // RightSimilar Crop Jeans (Size 2) | Chain Slide Mules (on sale!)

Abstract Mini Dress (35% off!) (C Multicolored Geometry, Small)
Similar Ankle Booties (TTS) | Layered Initial Necklace | Gold Bead Bracelets | Medium Hoop Earrings

Sweater Dress (Green & Brown, Small)
LeftBlock Heel Booties (Khaki, TTS) | Layered Initial Necklace | Gold Bead Bracelets
RightNotch Booties (TTS) | Similar Utility JacketPanama Hat

Blouson Sweater (On sale for $49!)
Similar Faded Jeans | Chain Slide Mules (on sale!) | Bracelet Set

Wide Leg Pants (Beige Short)
Button Down Shirt (Small) | Braided Slide Sandals (Apricot, TTS) | HeadbandMedium Hoop Earrings | Stretchy Bracelet

GLxHSP Decked Out Day Dress (code SUGARPLUM 10)
Strappy Heels (size up half) | Headband // Right: Levi’s Jean Jacket (Jeanie, Small) | Rothy’s Sneakers

Half-Zip Pullover (Style2-white, Small)
Wide Leg Ponte Pant (Small) (code SUGARPLUM10) | Cut-Out Sandals

Pleated Shoulder Sweater (Beige, Small)
Similar White JeansLeather Slide Sandals | Leather Woven Tote Bag | Headband

Tiered Mini Skirt (Caramel, Small)
Racerback Tank (Small) | Jean Jacket | Saddle Bag | Removable Strap (Stripe Rose Brown) | Cut-Out Sandals | Layered Initial Necklace | Gold Bead Bracelets | Medium Hoop Earrings

Notch Collar Blazer (XS) (code SUGARPLUM10)
Pocket Tee | Step Hem Jeans (size 26) | Chain Slide Mules (on sale!) | Initial Necklace

Waffle Weave Lounge Set (Apricot, Small)
Leather Slide Sandals | Leather Woven Tote Bag 

Wide Collar Pullover (Beige, Small)
Similar White JeansChain Slide Mules (on sale!) | Headband

Wowza, that was a lot! I hope this post inspired some fun new combos for you! What’s your go-to transitional style? We’re still rocking full-blown summer temps over here, but I’m ready when the chill arrives! Happy weekend, lovebugs!


Avara // Shop Sale HERE, plus 15% off full-priced styles with code CASSIE15

Colleen Rothschild // 20% off your purchase with code SUGARPLUM20

Gap // Up to 75% off sale styles, plus 30% off your purchase

Gibsonlook  // 10% off full-priced styles with code SUGARPLUM10

J.Crew // Up to 50% off select fall styles

J.Crew Factory // Up to 50% off everything, plus extra 15% off tops, shoes, accessories with code TIME2SHOP

Kendra Scott // Shop Sale HERE

LOFT // 40% off your purchase

Nordstrom // Up to 60% off during their Summer Sale

Old Navy // 30% off your purchase

Social Threads // 10% off full-priced styles with code SUGARPLUM10

tarte // 15% off eligible items with code CASSIE15

Leave a Comment


  1. Lisa wrote:

    Love the transition ideas! We’re slowly easing into cooler nights here in San Diego so it’s fun to see how to add some fall to my summer wardrobe.

    And thanks for making the font bigger – much easier to read. 😉

    Posted 9.8.23 Reply
    • Cassie wrote:

      Yes the font increase was necessary, ha! Still a learning curve with the updated site, so thank you for bearing with us!! xo, C

      Posted 9.9.23 Reply
  2. Jill wrote:

    That utility jumpsuit is stinkin cute…. Just like you. You always look great and hello long hair!! It’s gotten so long!

    Posted 9.8.23 Reply
    • Cassie wrote:

      That jumpsuit is such a good one-and-done outfit!!! xoxo, C

      Posted 9.9.23 Reply
  3. Cathy Fuller wrote:

    You look great in all the outfits!

    Posted 9.17.23 Reply
    • Cassie wrote:

      Thank you so much, Cathy!! xoxo, Cassie

      Posted 9.19.23 Reply