Photo by Janelle Olson, Styling by Emma Enebak
1. Retro Revelry
This sleek vintage typewriter will add an air of charm and sophistication to your home or office. Vintage typewriter, $98, Serge + Jane, sergeandjane.com
2. Half Moon Shine
Asymmetrical, dense, and dreamy, Aesther Ekme’s Demi Lune is your go-to “everything bag” for autumn. Demi Lune, $615, Idun, shopidun.com
3. Tied and true
Carrie Bradshaw called from the early aughts—and she says female ties are back. Embrace the androgynous accessory with these muted autumnal tones. Vintage pinstripe tie, $12, Queenie & Pearl, queenieandpearl.com
4. Peek of Pearls
Hang on to your pearls—the grandma-esque staple will reign supreme this season. ElaMariie Pearl and Pave Necklace, $325, Bumbershute, bumbershute.com
5. Sporty Sophistication
Embrace the best part of fall—the return of Sunday football—with this sporty bling by Viking football wife Whitney Risner’s brand Waawees. Waawees NFL Earrings and Pendant, $65 and $95, Bumbershute
6. Suit Up
With its subtle pinstripe, cinched silhouette, and deep burgundy hue, this retro blazer perfectly balances sophistication with style. Le Suit vintage blazer, $35, Queenie & Pearl
7. Burgundy Bliss
Transition from business-chic office wear to on-trend evening wear with these walkable burgundy loafers. Rag & Bone Burgundy Loafer, $328, Bumbershute
8. Mini but Mighty
Belt buckles on everything will be a recurring theme this season—embrace the trend with the Staud Harlow Bag—just big enough to fit a copy of “The Great Gatsby” (thank goodness). Staud Harlow Handbag, $325, Bumbershute
9. Pretty in Plaid
Plaid will be one of the most coveted patterns of the season, whether it’s on a stately trench coat or a sassy miniskirt—like this gold-accented showstopper by Ganni. Ganni check wool mini skirt, $345, MartinPatrick3, martinpatrick3.com
10. Read All About it
What’s more fashionable than reading? Possibly only doing so in these chic oversized Caddis readers from Bumbershute. Caddis D28 Rx Glasses, $310, Bumbershute
11. A Pop of Cherry
Belts are for more than just for function this season, and this elegant cherry leather Cliff belt proves it. Cliff belt, $215, Idun
12. Mix it Up
Mixed metal statement pieces will bring an eclectic edge to your neutral fall tones. Pair these ElaMariie earrings with this simple gold chain to sparkle through the season. ElaMariie Mixed Metal Pave Earrings and Snake Necklace, $245 and $125, Bumbershute
13. Jockey Dreams
Horse girls are finally having their moment—ace fall fashion this season with equestrian inspired motifs like this printed silk scarf from Queenie & Pearl. Vintage Scarf, $10, Queenie & Pearl
14. Booked and Busy
This 1996 Ghurka Tilbury leather satchel feels like it was pulled straight from “The Dead Poets Society,” a dreamy vintage relic that will carry you through autumns to come. Ghurka Tilbury No. 126 Leather Satchel, $700, June, juneresale.com
15. Back in the Saddle
This year’s fall fashion curriculum calls for a sleek and versatile pair of riding boots—and these shiny mocha knee-highs ace the test. Tall Thora Boot, $575, Idun
16. Sweet as Chocolate
Embrace Pantone’s 2025 color of the year—mocha mousse—with this chocolate-hued cardigan, perfect for throwing over your shoulders in the uncertain September temps. Hayden Cardigan, $48, Queenie & Pearl
