30 Fall Transitional Styles

Happy Friday, friends, and cheers to the weekend! First up, thank you so much for the love and encouragement regarding our big announcement (catch up on things HERE)! I can’t explain how good it feels to be supported through such a big life change, not to mention, the encouragement from fellow moms who understand our need to support Sloan.

Parenting in general is hard, and parenting a child through grief has felt overwhelming at times. But to have the support of a community of incredible women (and a few men, ha!), has truly lifted me up each day. So thank you… your presence here means more to me than I can adequately describe.

Please know that I’m continually praying for each of you and this community, as well. Life is full of curveballs, but I hope you know you aren’t alone, and we’re all just doing the best we can… and your best is more than enough!

Okay, gushing over for now… today we’re talking 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 formula for transitional seasons is usually to cover either my arms or my legs… that way I’m straddling the heat of summer and the chill of fall. 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 hard to beat!

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!

Similar Striped Tee | Utility Jacket (Size: XS) | Step Hem Jeans  | Similar Sneakers

Spotty Drop Waist Dress (Size: Small, Color: Leopard Pink) | Strappy Heels (size up half) | Initial Necklace

Scoopneck Tank | Notch Collar Blazer (Size: XXS)| Midi SkirtStrappy Heels (size up half) | Initial Necklace

Dolman Sweater (code SUGARPLUM10 to save 10%) (Size: Small, size up for leggings) | White Jeans | Chain Mules

Chunky Cardigan (Size: Small, Color: Beige) | Racerback Tank (Size: Small) | Tiered Mini Skirt (Size: Small, Color: Caramel) | Cut-Out Sandals | Initial Necklace

Sleeveless Midi Dress (Size: Small, Color: Gray) | Cut-Out Sandals | Initial Necklace | Jean Jacket

Floral Long Sleeve Top (Size: XS, code SUGARPLUM10 to save 10%) | Step Hem Jeans | Block Heel Booties (TTS, Color: Khaki)

Striped Utility Blouse (Size: Small, Color: Red) | White Jeans (code SUGARPLUM10 to save 10%) | Cut-Out Sandals

Swiss Dot Maxi Dress (Size: Small, Color: Purple) | Cut-Out Sandals | Initial Necklace | Gold Hoop Earrings | Jean Jacket

Notch Collar Blazer (Size: XXS, Color: Latte) | Tie Waist Chiffon Dress (Size: Small, Color: Flower Black) | Strappy Heels (size up half)

Utility Pocket Shirtdress (Size: Small) | Block Heel Booties (TTS, Color: Khaki) | Panama Hat

Smocked Midi Dress (Size: Small, Color: Red Flower) | Cut-Out Sandals | Initial Necklace | Jean Jacket

Mock Neck Sweater (Size: XS, code SUGARPLUM10 to save 10%) | White Jeans | Chain Mules

Ribbed Sweater Set (Size: XS, Color: Dark Chestnut Brown Heather) | Booties (size up half) | Gold Bead Bracelets | Layered Pendant Necklace

Floral Long Sleeve Dress (Size: XS, code SUGARPLUM10 to save 10%) | Block Heel Booties (TTS, Color: Nude) | Jean JacketInitial Necklace

Chunky Cardigan (Size: Small, Color: Dark Pink) | Racerback TankWhite Jeans (code SUGARPLUM10 to save 10%) | Block Heel Booties (TTS, Color: Khaki) | Initial Necklace

Henley Puff Sleeve Blouse (Size: XS, code SUGARPLUM10 to save 10%) | Notch Collar Blazer (Size: XXS, Color: Latte) | Straight Leg Jeans | Loafers

Ruffled Romper (Size: Small, Color: Orange) | Block Heel Booties (TTS, Color: Khaki) | Initial Necklace

Half-Zip Pullover (Size: Small, Color: Style2-white) | White Jeans (code SUGARPLUM10 to save 10%) | Chain Mules | Initial Necklace

Floral Maxi Skirt (Size: Small, Color: Yellow) | Racerback Tank (Size: Small, Color: Khaki [No Coffee]) | Jean Jacket | Cut-Out Sandals | Initial Necklace

Batwing Sweater (Size: XS) | Faux Leather Leggings | Leopard Loafers | Gold Bead Bracelets

Tiered Mini Skirt (Size: Small, Color: Caramel) | Racerback Tank (Size: Small, Color: Khaki [No Coffee]) | Jean Jacket | Cut-Out Sandals | Initial Necklace

Wide Leg Pants (Size: Medium, Color: Cwblp138_black) | Half-Zip Pullover (Color: Style2-white) | Racerback Tank (Color: 1white) | Cut-Out Sandals | Initial Necklace

Notch Collar Blazer (Size: XXS, Color: Latte) | Spotty Drop Waist Dress (Size: Small) | Strappy Heels (size up half)

Decked Out Day Dress (Size: XXS, code SUGARPLUM10 to save 10%) | Braided Heels (Look For Less HERE) | Initial Necklace

Tie Waist Dress (Size: XS, code SUGARPLUM10 to save 10%) | Braided Heels (Look For Less HERE) | Initial Necklace

Sleeveless Maxi Dress (Size: XS) | Cut-Out Sandals | Initial Necklace | Jean Jacket

Flutter Sleeve Swing Dress (Size: Small) | Block Heel Booties (TTS, Color: Khaki) | Utility Jacket (Size: XS) | Initial Necklace

Boho Blouse (Size: XS, code SUGARPLUM10 to save 10%) | Straight Leg Jeans | Chain Mules | Initial Necklace

Ruffle Neck Blouse (Size: XS, code SUGARPLUM10 to save 10%) | Step Hem Jeans | LoafersInitial Necklace

Double Breasted Blazer (Size: Small, prefer my normal XS; code SUGARPLUM10 to save 10%) | White Jeans | Chain MulesInitial Necklace


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 //  Up to 30% off select faves, plus 20% off your purchase with code SUGARPLUM20

Evereve // Shop Sale HERE, plus free shipping on orders $50+

Gap // Extra 50% off sale styles with code GOSHOP, plus an extra 20% off activewear with code COMFY

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

J.Crew // Up to 40% off select women’s styles and kidswear

J.Crew Factory // All jeans under $50

Kendra Scott // Shop Sale HERE

LOFT // 30% off fall faves with code GOOD

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

Old Navy // 30% off your purchase, even clearance

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

tarte // 15% off eligible items with code CASSIE15

Leave a Comment


  1. Sandy wrote:

    Laugh and smile for the day-the pup is in a different pose in each photo, ha,ha. xo.

    Posted 9.9.22 Reply
    • Cassie wrote:

      HAHAHA you’re so right, Sandy!!! xo, C

      Posted 9.9.22 Reply
  2. Lisa wrote:

    Lots of fun ideas here! My go-to uniform is a variation of t-shirt/tank and shorts/jeans (or, who am I kidding, Vurori’s haha). SoCal is still warm in fall so those jean and utility jackets come in handy. Thanks for all the inspo! xo

    Posted 9.9.22 Reply
    • Cassie wrote:

      Hi Lisa! You sound like a girl after my own heart! You better believe my Vuoris will be on mega repeat this season! xo, C

      Posted 9.9.22 Reply
  3. Dana wrote:

    Your daughter’s name is so great! I love that name. Thank you for the inspiration! Have you read a Praying Life by Paul Miller? I just finished it. It was phenomenal.

    Posted 9.14.22 Reply
    • Cassie wrote:

      Oh thank you so much, Dana!! I haven’t read that one but maybe I should add it to my “to-read” list! xo, C

      Posted 9.14.22 Reply