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It’s safe to say the actress’s part in the series finale of Mad Men was life-changing. She played a counselor at a spiritual retreat who made a profound impression on the show’s protagonist, Don Draper, the role immortalized by Jon Hamm. A few years later, Hamm and Osceola began dating and married in 2023. They’re currently filming the second season of Your Friends & Neighbors (Apple TV+), in which Hamm stars as a disgraced hedge-fund hotshot who begins burglarizing his wealthy neighbors, one of whom is played by Osceola. Here, she shares her picks for a home worth pilfering.

Pierre Chapo

$19,330

Vintage S11 Dining Chairs, Set of Six

“The first piece of furniture I purchased when my husband and I started renovating our NYC apartment. I am obsessed with Pierre Chapo and his S11 chair Sixties French elm + cognac leather = perfection.”

Matiere Premiere

$290

Neroli Oranger Eau de Parfum

“I discovered this perfume at Chez Dede in Rome. It smells like early spring in Southern California. I’ve never been more complimented on a scent.”

Byredo

$99

Burning Rose Candle

“My all time favorite candle. We had them burning at my wedding reception, so now it evokes the dreamy memory of Big Sur in late June.”

Newey & Bloomer

$459.95

Simplex Kensington Tea Kettle

“Nickey Kehoe has the most impeccably curated stores in LA and now NYC. I love this classic copper kettle from Newey & Bloomer. It patinas beautifully and also makes a great wedding gift.”

Public Supply

$12

5x8” Soft Cover Notebook - Red

“I’m a dedicated list-maker and hate using my phone. I love the colors and classic scholastic style of this one. Plus, 25 percent of their profits go to supporting creative work in public schools, a wildly worthy cause.”

Eres

$225

Mouna Bikini Top

“Eres makes the perfect bikini. I can’t divulge how many different colors I have in my collection, which won’t be complete anytime soon. I like to un-loop the straps and turn it into a classic halter top.”

Globe-Trotter

$3,095

Centenary Leather-Trimmed Suitcase

“This luggage is timeless and gets better with age. As a shameless over packer, I’m particularly fond of their XL trunk. Not complete without a monogram.”

Moleskine

$25

Classic 2025 Weekly Planner

“I’ve kept a yearly agenda book since high school. I can always look back to see where I was and what I was up to. Moleskine makes my favorite hardcover version that, of course, begs to be monogrammed.”

Autumn Sonata

$88

Alma Bath Towel

“I am in love with this print. These towels are incredibly soft, absorbent, and look fabulous.”

Del Toro

$248

Vintage Club V-Neck Sweater - Forest Green

“First, my husband ordered this sweater in navy, which I immediately coopted. Then I bought my own in crimson. Then got another in green.”


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