Ditch the ‘shoulds’: Dress for your actual life, not an idealized version

I am absolutely fed up with the relentless, unspoken pressure on women, especially those more than 40, to dress for some idealized version of themselves. 😤 Forget the aspirational wardrobes and the “shoulds”—I want to scream from the rooftops that your clothes should fit the life you actually live, not the one you wish you had.

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You’d think fashion, by its very nature, would be about expressing who you are, right? A simple, joyful connection between your inner self-and your outer presentation. Easy. Au contraire! 🤔

I remember one particular fashion insider who perfectly encapsulates this style evolution. She was a former Vogue editor, gracing One World Trade Center daily in a floral dress and heels.

Her life looked one way and her closet reflected that polished, high-fashion world. Then came a pivot. This savvy entrepreneur started her own beauty brand, 14th Night, trading editorial meetings for running around the city to meet formulators and retailers, test products or source ingredients.

Her days looked different and so did her style. She found herself constantly reaching for the same pair of vintage Levi’s orange tab 517s from the 70s.

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These jeans, with their light creases and subtle flare, fit her perfectly and could be dressed up for meetings with a blazer. It’s a stark, wonderful image: swapping aspirational for authentic.

The good news is, some voices in the industry are actually getting it right. Sierra Mayhew, a fashion editor at Who What Wear, brings a decade of industry experience from her time at Harper’s Bazaar and Elle, not to mention her alma mater, the University of Notre Dame. ✨

Mayhew, who joined Who What Wear in 2021, has since become a champion for real-life style. She insists that there’s “no one-size-fits-all answer” to how a 40-year-old woman should dress.

Her golden rule? “It’s all about choosing clothes that make you feel good instead of worrying about what society expects you to wear.” Mayhew frames style not as a static rulebook but as “a whole playlist,” acknowledging that “some days you’re classic, other days chic, bold, sporty, boho, or feminine.” 😎

The trick, she notes, is to find “staples that can flex with every version of you.” She even updated her list of 14 closet essentials to help women do just that.

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It’s a pragmatic, personal approach that cuts through the noise.

So next time you’re staring at your closet, wondering “Where am I going in that?,” remember: the only right answer is “to live my life.” 💖