Kiernan Shipka's Stunning Style Transformation Since Mad Men Ended

Kiernan Shipka was only 7 years old when she debuted as Sally Draper on "Mad Men," with the Chicago native growing up on-screen throughout the series' seven seasons. While the gripping period drama was formative for Shipka's acting career, remaining one of her most noteworthy roles to date, it also had a major influence on her fashion journey. "Being on the show allowed me to find my own style and express it in a big, bold way," she told InStyle back in 2016. "I wasn't thinking too much about fashion when I started on Mad Men, to be honest ... But once I started going to fittings and being exposed to the costumes, it was eye-opening from that point forward" (per Yahoo!).

Since "Mad Men" aired its finale in May 2015, the award-winning actor has gone on to land several notable roles, starring in the Netflix series "The Chilling Adventures of Sabrina" and headlining films like "Wildflower" and "Totally Killer." At the same time, Shipka has also experienced a stunning style transformation as she's gone from teen star to adult actor. From designer red carpet looks to trendy street style, here's a look at how much Shipka's style has evolved over the years.

Kiernan Shipka had already established herself as a high-fashion lover by the time "Mad Men" ended in 2015, often wearing couture looks to star-studded events. As an example, the Chicago native wore a doodle-style, flower print Giambattista Valli dress to the CFDA/Vogue Fashion Fund Show in 2015. The designer garment had a mod dress-inspired shape, featuring a textured pattern and lace-trimmed, ruffle sleeves. The "Sweethearts" star styled the dress with a double-braided hairstyle, studded clutch, and black, pointed-toe heels.

Celebrity stylist Jill Lincoln, who partnered with Jordan Johnson to style Shipka throughout her early career, provided some insight into the actor's fashion sense during this time. "We play with shapes and A-lines and looks that are more partial to the 'fashion' element of it than that make her appeal to the masses," Lincoln told Fashionista. "She does some things sometimes that women who don't live in major fashion cities might not quite get. It's more about fun. It's fun, it's fashion. It's ultimately what she likes to wear versus what's going to make everyone else happy."

As her teen years progressed, Kiernan Shipka's fashion was characterized by classic vibes and vintage silhouettes paired with fun style elements. The "Swimming with Sharks" star was spotted at the 74th Venice Film Festival in 2017 wearing such an ensemble, with the actor being unsurprisingly dressed in head-to-toe Miu Miu. She combined a smock-waist dress featuring slightly puffed sleeves and a Peter Pan collar with platform, sandal-style heels, a suede clutch, and butterfly sunglasses.

While the shape and print of the dress feel very vintage, Shipka effectively kept it young and fresh with her styling and accessorizing. We think the celeb described it best when she defined her fashion sense in three words. "Fun, because I like to have a lot of fun with what I wear. I mean, to me that's what style is about," she told W Magazine in 2015. "Casual — I'm a pretty casual person in the everyday sort of realm. And classic, because I really like pieces that I can wear over and over again."

The "Chilling Adventures of Sabrina" marks another major era for Kiernan Shipka, as she starred as the titular Sabrina Spellman in the teen Netflix show. The adaptation is a darker reimaging of the original comic series, equipped with atmospheric settings and occult elements, though its approach to horror and inclusion of social themes are often compared to "Buffy the Vampire Slayer." While it's not the witchy '90s aesthetic of "Practical Magic," the fashion and atmosphere of the TV series have influenced some of its star's real-life looks.

An example of this comes from the LA premiere of "Chilling Adventures of Sabrina" in 2018, where Shipka combined her vogue fashion sense with the show's dark aesthetic by sporting an Elie Saab mini dress. The red and black garment was embellished with sparkly paillettes, giving it a beautifully textured look that the celeb paired with bow-wrapped, pointed-toe heels and a simple velvet clutch. While Shipka maintained much of her vintage-inspired and fun-feeling style elements throughout the four seasons of the Netflix series, this era revealed that the style icon isn't afraid of a little method dressing.

While things seemed to slow down for the actor in the early 2020s following the wrap of the "Chilling Adventures of Sabrina," Kiernan Shipka came back hot in 2022. Not only did she have the coming-of-age film "Wildflower" and the gripping series "Swimming with Sharks" on the docket that year, but she also really upped her street style. The fashion icon had previously described her style as casual, with fans getting glimpses of her off-duty looks over the years through sporadic paparazzi sightings, but 2022 marked several trendy street sightings for the celeb.

Among our favorites is the outfit that Shipka wore in late August in New York City, which managed to style camo in a way that is actually fashionable. For the effortlessly cool look, she paired camo-printed, tapered pants with a black, cropped cardigan from Miu Miu. The TV star styled the pieces with heeled combat boots, a polka-dotted handbag, a gold necklace, and circle sunglasses. While Shipka had proved herself to be a couture-wearing style icon on the red carpet, this outfit is a testament to her trendy sense of streetwear.

As of 2024, Kiernan Shipka has established herself as a confident style icon, and a force to be reckoned with on-screen, appearing in the gritty horror movie "Longlegs," the nostalgic, action flick "Twisters," and the lighthearted romcom "Sweethearts" all within a year. "I really feel like, for the first time in a minute, I know my style," she told Byrdie in 2023. "I know what looks good on me, what I feel comfortable in, and I just don't want to leave the house not feeling like myself." The movie star has simplified her wardrobe in some ways, telling the outlet, "I like simpler things these days. I like going more streamlined. I wear a lot of black."

Still, her most current fashion is characterized by self-possessing confidence that allows her to wear high-fashion pieces with the same ease as street style. An example of this is the stunning black gown that she wore to the Nina Ricci runway show during Paris Fashion Week. The floor-length garment, designed by Ricci, features a full-stomach cutout trimmed with lace under a V-shaped neckline with a tie front. Shipka paired the revealing dress with a gold necklace, a long, black cardigan, and platform shoes. Stunning!