What to Wear to Thanksgiving

With Guest Editor Olivia Wayman, the London-based stylist behind Olivia's Shopping Diary.

Nov 14, 2023

One of my resolutions for 2024 is to bring more contributors to the newsletter, and not just from within my immediate network. Fresh perspectives are needed after almost three years of my singular voice. They say you should hire to your weaknesses. Since I am neither a. in my 20s nor b. good at TikTok, my first order of business was asking a few friends who are both to have a run at our “Inbox Stylist” vertical.

Olivia Wayman is the London-based wardrobe stylist behind Olivia’s Shopping Diary. Her popular TikTok account combines aesthetically pleasing wardrobe edits, shopping discoveries, and fashion snippets from her UK life. She favors the minimal and modern, mixing easy classics in a simple, wearable way that still feels aspirational and editorial. If you’ve ever gone on an Olsen fashion deep-dive, your algo has probably proffered her content.

I asked her to imagine an edit of Thanksgiving archetypes to help guide your own “what to wear” come this Turkey Day.

You can find Olivia on TikTok, Substack, and Instagram.

THE FRESHLY MINTED CITY GIRL

“Whilst she grew up in the rural countryside, she moved to the city last summer to pursue a career in fashion. Maintaining her internship with a fledging career in content creation is a delicate balance, but she does it well. Home for Thanksgiving with 2500 new Instagram followers, she teaches her high school friends what a Hugo Spritz is.” Jacket, Tibi. Hand cream, Byredo. Bag, The Row. Sneakers, Onitsuka Tiger. Jeans, AGolde. Belt and Earrings, Aureum Collective. Sunglasses, Oliver Peoples. Fragrance, Santal Rose 31.

THE WEST COAST HOSTESS

“To her, Goop is religion, and hosting is an Olympic Sport. She put in her pickup order at Erewhon weeks ago, but she’s still losing sleep over the seating plan. Her Pinterest is full of Carolyn Bessette Kennedy street-style pictures, and the algorithm pushes her all things ‘Clean Girl Aesthetic.’ Her spotless dishes are as white as her pressed cotton shirt. She has never been inside a Wal-Mart.” Sweater, G.Label. Shirt, The Row. Earrings, Lié Studio. Pot, Greenpan. Loafers, Hereu. Jeans, Citizens of Humanity. Book, CBK: A Life in Fashion. Tote, Millenial Decorator. Shampoo, Act + Acre. Moisturizer, Goopgenes.

THE HOMETOWN HOMEBODY

“Comfort reigns over fashion when it comes time for Mom’s pecan pie. She plans to spend the entire holiday between the dining table, kitchen, and couch, lazing around with family and telling absolutely no one she’s in town. Her only outing is with her cousin to smoke weed and hit Starbucks, where she orders her usual oat flat white with exactly one pump of celebratory Pumpkin Spice syrup.” Sweater, Khaite. Pants, Citizens of Humanity. Bag, Khaite. Necklace, Lié Studio. Earrings, Dorsey. Hat, Alex Eagle Sporting Club. Sunglasses, Khaite. Sneakers, Adidas x Wales Bonner.

THE SOCIAL BUTTERFLY

“She’s the life of the party, and she knows it. She’ll spend Thanksgiving everywhere and nowhere, drifting in and out of overly fussy dinners at each of her divorced parents’ houses, still hung over (and in the same dress) from a huge night out on Wednesday. She always has a light — both ring and cigarette. After waking up in her hometown ex’s bed on Friday, she’ll sneak home to her Mom’s for a turkey sandwich, a shame spiral, and a smoke.” Earrings, Lié Studio. Coupe Glasses, Fferrone. Contour Stick, Westman Atelier. 90s Bag, The Row. Loafers, Freda Salvador. Charm Necklace, Lilly Sisto x Hart. Leather Jacket, Dunst. Dress, Rabanne.

THE REVENGE SEEKER

“She’s had a crush on him since grade school, and last Thanksgiving, they finally hooked up. It was great until he weaponized his family trauma as an excuse to cheat on her. Twice. She should have known when he asked to split the bill on their first date. She hasn’t spoken to him since he ghosted her on Valentine’s Day. This year, she’s going to make an entrance — and she’s serving a revenge outfit as cold as her martini.” Fragrance, Byredo Gypsy Water. Hair Pin, Deborah Pagani. Gemelli Bag, Bottega Veneta. Pumps, The Row. Cardigan, Khaite. Shorts, Wardrobe.nyc. Coat, Nilli Lotan. Necklace, Vintage Elsa Peretti for Tiffany.