34 Transitional Fall Styles

Happy Friday, friends, and cheers to the weekend! It’s our last day in Martha’s Vineyard before heading home tomorrow. As much as I love travel, I’m ready to give my trusty carry-on a break and enjoy the fall season at home!

Texas really shines this time of year, and I can’t wait to soak it all up. Plus, we’ve got Family Weekend next month, and I’m counting down the days until we see Sloan!

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!

Here are 34 styles to inspire you for the new season… whether you’re headed to work, running errands around town, or traveling the world… there’s a little something for everyone!

Transitional Styles //

Gingham Maxi Dress | Leather Jacket | Leather Slide Sandals | Handbag | Charm Necklace | Full Details HERE

Cashmere Crewneck (Small) | Relaxed Straight Leg Jeans | Clear Toe Strap Sandals | Station Necklace | Dome Hoop Earrings | Love Bracelet | DY Heart Bracelet | Chain Link Bangle | Tennis Bracelet | Shop All HERE

Blush Floral Blouse (XS) (code CASSIE15) | Patch Pocket Jeans in ‘White’ (size 26) (Similar HERE) (code CASSIE15) | Station Necklace | Dome Hoop Earrings | Love Bracelet | DY Heart Bracelet | Chain Link Bangle | Tennis Bracelet | Shop All HERE

Drop Waist Midi Dress (Black & White) | Striped Cardigan (XS) | Mary Jane Ballet Flats | Puffy Heart Toggle Necklace | Dome Hoop Earrings | Love Bracelet | DY Heart Bracelet | Chain Link Bangle | Tennis Bracelet | Shop All HERE

Pink Quilted Jacket (Small) | Dark Wash Crop Jeans (size 26) | Buckle Mules | Sunglasses | Station Necklace | Thin Gold Hoop Earrings | Full Outfit HERE

Satin Slip Dress (Small) | Cashmere Crewneck (Small) | Clear Toe Strap Sandals | Embroidered Clutch | Shop All HERE

Tank Midi Dress (Small) | Similar Ballet Flats | Full Outfit HERE

Cashmere Cardigan (XS) | Tank (Small) | Jeans (size 26) | Slide Sandals | Sling Bag | Beaded Necklace | Full Outfit HERE

Paisley Long Sleeve Dress (XS) (code CASSIE15) | Tall Boots | White Handbag | Sunglasses | Teardrop Earrings | Love Bracelet | DY Heart Bracelet | Chain Link Bangle | Tennis Bracelet | Full Outfit HERE

Striped Floral Blouse (XS) (code CASSIE15) | Patch Pocket Jeans in ‘White’ (size 26) (Similar HERE) (code CASSIE15) | Station Necklace | Dome Hoop Earrings | Love Bracelet | DY Heart Bracelet | Chain Link Bangle | Tennis Bracelet | Shop All HERE

Leather Jacket | Crewneck Tee | Relaxed Straight Leg Jeans | Gola Sneakers | Hat | Shop All HERE

Striped Crewneck (White Camel Stripe, Small) | Raw Hem Wide Leg Jeans | Woven Flats (A Tan Woven) | Puffy Heart Toggle Necklace | Dome Hoop Earrings | Love Bracelet | DY Heart Bracelet | Chain Link Bangle | Tennis Bracelet | Shop All HERE

Gingham Tie-Waist Dress (XS) | Leather Slide Sandals | Beaded Necklace | Puffy Heart Earrings | Bracelet

Peplum Midi Dress (XS) | Similar Ballet Flats | Button Cardigan (Fc280_khaki, Small) | Gold Hoop Earrings | Tennis Bracelet | Shop All HERE

Corduroy Ruffle Dress (XS) (code CASSIE15) | Mary Jane Ballet Flats (Also HERE) | Handbag | Scarf | Shop All HERE

Striped Cardigan (Caramelred and Black-White, XS)
Left: Seamed Risen Jeans | Mary Jane Ballet Flats (Also HERE) | Teardrop Earrings | Tennis Bracelet // Right: Similar Light Wash Jeans (code CASSIE15) | Bow Ballet Flats (TTS) | Short Double Strap Tote Bag | Shop All HERE

Cinched Waist Shirtdress (Green, Small) | Leopard Ballet Flats | Gemstone Drop Earrings | Love Bracelet | DY Heart Bracelet | Chain Link Bangle | Tennis Bracelet | Shop All HERE

Racerback Midi Dress (Black, Small) | Similar Ballet Flats | Striped Cardigan (Black-White, XS) | Double Strap Tote Bag | Scarf | Teardrop Earrings | Tennis Bracelet

Oversized Shirtdress (Black, Small)
Left: Black Slide Sandals (Similar HERE) | Dome Hoop Earrings | Love Bracelet | DY Heart Bracelet | Chain Link Bangle | Tennis Bracelet // Right: Striped Cardigan | Leopard Ballet Flats | Shop All HERE

Tiered Long Sleeve Dress (XXS) | Sneakers | Studded Bag | Gold Aviators | Gold Hoop Earrings | All-Weather Bangles | Shop All HERE

Belted Shirtdress (Navy, Small) | Woven Flats (A Tan Woven) | Boxy Tote Bag | Gemstone Drop Earrings | Love Bracelet | DY Heart Bracelet | Chain Link Bangle | Tennis Bracelet | Shop All HERE

AirEssentials Zip Pullover | AirEssentials Wide Leg Pants | NB 327 Sneakers (Also HERE)

A-Line Henley Dress (Army Green, Small) | Woven Flats (A Tan Woven) | Woven Suede Shoulder Bag | Gemstone Drop Earrings | Love Bracelet | DY Heart Bracelet | Chain Link Bangle | Tennis Bracelet | Shop All HERE

Ruffle Puff Sleeve Blouse (XS) (code CASSIE15) | Patch Pocket Jeans in ‘Khaki’ (size 26) (Similar HERE) (code CASSIE15) | Station Necklace | Dome Hoop Earrings | Love Bracelet | DY Heart Bracelet | Chain Link Bangle | Tennis Bracelet | Shop All HERE

Mock Neck Sleeveless Midi Dress (Brown, Small) | Mary Jane Ballet Flats (Also HERE) | Jean Jacket (Jeanie, Small) | Sneakers | Gold Hoop Earrings | Tennis Bracelet

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

Long Button Vest (Small) | White Wide Leg Jeans | Mary Jane Ballet Flats (Also HERE) | Bangles

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

Open Pocket Cardigan (Solid Beige, Small)
Left: Pocket Tee (Small) | Similar White Jeans | Cut-Out Sandals | Layered Initial Necklace // Right: Similar Crop Jeans | Similar Chain Mules

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

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

Faux Leather Mini Dress (XS) | Suede Ballet Flats | Shop All HERE

Sleeveless Sweater Dress (XS) | Tall Boots | Shop All HERE

Plaid Shirtdress (XXS) | Suede Pumps | Studded Clutch | Shop All HERE

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!

In case you missed it, I shared my Amazon Beauty Faves HERE, my latest Amazon Fashion Finds HERE, and my recent Avara work trip to Aspen HERE. Happy Friday, lovebugs!