About fifteen minutes into R.J. Cutler’s Netflix documentary Martha, Martha Stewart reveals she kissed a stranger on her honeymoon. “It was neither naughty nor unfaithful,” says Stewart. “It was just emotional and of the moment.” It is this precise combination of nuance and paradox that goes on to define so many aspects of Stewart—but also, becomes the throughline for the audience to wrestle with for the rest of the film.
How does she speak so pridefully on monogamy, yet flippantly acknowledge her own marital indiscretions? Is she the original trad wife? Or was that just what she was selling, and she was actually never really capable of being a housewife at all? Were the criminal charges simply a famous woman being exploited and made an example of? Or was she truly guilty of obstruction of justice? And, in the end, does any of it even matter? Considering her accomplishments and import, these paradoxes manage to avoid feeling hypocritical. They actually just make her all the more singular. As her friend Lloyd Allen puts it, “She was the first woman that saw the marketability of her personal life. Martha was the first influencer.”
From encasing a Thanksgiving turkey in puff pastry (to give it that extra oomph), to trimming her hedges to the precise right height, Stewart’s influence lies in her attention to detail (within another detail). But while her perfectionistic tendencies in the home may come as no surprise—her incredible fashion sense and timeless style just might. To accompany her distinct Cotswolds meets Provence with a heavy dose of Connecticut home aesthetic, the cultural icon’s fashion sense presents its own masterful set of paradoxical quandaries—namely, was her style Wall Street cosmopolitan or country club cozy? From belted slacks with tucked-in t-shirts to oversized blazers with leggings to perfectly crisp button-ups with pearls and LL Bean rubber clogs, Stewart’s fashion sense is as good as her cakes—they remain utterly timeless and exciting. Ahead, take a look back at some of her best looks from the doc and beyond.
The silver ball studs pair perfectly with a crisp white collar peeking out from under the burgundy cashmere sweater. For the former, these Sidney Garber studs are perfect.
Excuse us while we look for a soft headscarf to pair with our khaki barn coat.
When it comes to investing in forever pieces, Stewart teaches us that nothing stands the test of time better than a well tailored two-piece skirt suit.
Got a holiday party around the corner? Why not pull a Martha and pair a slinky little black minidress with an oversized pendant necklace for a classic ’60s throwback.
The wall quilt seems of equal importance to the cozy, oversized striped long sleeve tee. Time to search Etsy for both.
Sitting at the diner with her daughter Alexis, Stewart wears round acetate sunnies, a white turtleneck neck, and a collared jacket, for a look that’s as chic today as it was more than fifty years ago. Think Attersee meets Agnès B.
Pasta from scratch, but make it cute. Looks like Calvin Klein still sells a very similar little red t-shirt.
Another day, another great head scarf moment with Stewart’s minimalist all black ensemble.
A cozy cashmere sweater, dark jeans, and a simple barrette—Stewart’s version of quiet luxury hits the mark.
It may be 1976, yet the queen of entertaining’s red dress and long gold chain here reads not the slightest bit dated.
For a dressier night, Stewart, pictured here at the Lenox Hill Hospital benefit in 1991, paired a well-tailored black dress with a matching pearl earring and necklace set.
Stewart, seen here with her ex-husband Andrew Stewart, pairs a classic pair of LL Bean Duck Boots with dark denim and a bomber jacket.