Preppy Outfits Diaries – September 2026

September started off strong with landing in Glasgow, Scotland for a chilly week that was the ultimate Sweater Weather preview and also ended on a chilly note with Sweater Weather in the Washington, DC area and crushing my professional goals as well as hosting 2 Fall Dinner parties. Truly, I feel so grateful for September 2026 and enjoyed wearing SOOO many fun Fall preppy outfits to commemorate the start of the season!

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Preppy Outfits Diaries – September 2026

My Favorite Pieces

Whether it be feeling ultra-confident in the hottest floral jacket of the season to run errands, snuggling up in my favorite two-piece knit sweater-skirt set, or taking my favorite vegan leather bag on the town, my preppy outfits this past September truly lived up to the hype and found myself gravitating towards the same staples again and again!

This month, I decided to do something a bit different and share some of my favorite pieces that I used with some of my favorite preppy outfits, including a blanket and some newly-purchased wine glasses.

 

My Outfits

midi dress with a green and red floral block print, puff sleeves, and a tied waist - Preppy Outfits

pink long-sleeve pullover and matching scalloped skort set

black-and-white striped long-sleeve top paired with relaxed light-wash barrel-leg jeans and black flats - Preppy Outfits

a green floral print smocked-waist poplin midi dress paired with a canvas tote bag

Umgee Floral Midi Dress With Ruffle Trim And Elastic Waist

Willa Midi Dress in Mountain Bluebird from J.Crew Factory - Preppy Outfits

purple striped long-sleeve shirt, dark skirt, black knee-high boots, and Louis Vuitton monogram tote bag

navy blue sweater, paired with black leggings and dark tall rain boots - Preppy Outfits

white long-sleeve dress paired with a pink plaid scarf and dark tall rain boots

black-and-white floral jacket, pink pants, and a brown monogram tote bag

black mini dress paired with a patterned neck scarf

The Ellie Nap Dress by Hill House Home - Preppy Outfits

beige scalloped-edge trench coat over green gingham pants

the Bagheera - Now or Later Skirt in Hot Pink by Printfresh - Preppy Outfits

pink floral Lilly Pulitzer top and gold jewelry

pink short-sleeve tweed dress paired with tall black rain boots

bright pink button-front jacket paired with tall black rain boots and Monogram canvas tote bag - Preppy Outfits

floral print zip-up jacket paired with a black midi skirt and bright pink handbag

quilted puffer vest over a cream sweater, magenta pants, tall black rain boots, and a Louis Vuitton Neverfull MM monogram tote bag

floral blouse paired with light-colored, wide-leg satin trousers - Preppy Outfits

Lilly Pulitzer maxi dress with a wrap skirt and white lace trim

 pink plaid tunic paired with classic tall black boots - Preppy Outfits

checked oversized jacket with a vibrant magenta top and matching trousers

pink Lilly Pulitzer Pollie Midi Dress -Preppy Outfits

Wrap-Up

Here’s to styling some more outfits into the Sweater Weather months (and beyond!)!

XOXO – Katie <3