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Exactly six years ago, I went to see our forever FLOTUS in New Jersey; you can read that post here. Last night, as fate (and good timing) would have it, I got to see her again, this time in conversation with my fellow Scorpio and ultimate fashion queen, Tracee Ellis Ross. Talk about a full-circle moment!
Her new book, THE LOOK, celebrates the story behind her style, from her iconic moments as the First Black First Lady to the chapter she’s in now. And while you might think it’s just a gorgeous coffee-table book (which it is), it’s also filled with essays where she breaks down the thought, intention, and purpose behind the outfits and hairstyles we’ve all come to know and love. I’ll share some takeaways from the conversation that spoke to me below!
Michelle is just like so many of us; she grew up not being able to afford the latest fashions, dreaming about how she’d look and what she’d buy once she had her own money. Her mom, Marian Robinson, sewed most (if not all) of her clothes, while Michelle dreamed of Gloria Vanderbilt jeans, Polo shirts, K-Swiss, and Stan Smith sneakers — the must-have items in Chicago at the time.
That part of her story really resonated with me. It reminded me of how I started building my own sneaker collection later in life, making up for all the fly kicks I couldn’t afford as a kid.
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Another huge takeaway for me was her openness about natural hair, and the conversation around how women, especially Black women, are judged by their hairstyles. Michelle’s hair has always been laid, beautiful, and bouncy since we’ve known her. Every time she stepped out in public, not a strand was out of place, and that was by design. She knew that how she presented herself would always be a topic of discussion.
And while that silk press stayed pressed, hunny, it was also the safest style she felt America could handle while she served as First Lady. But there’s a new freedom about her now, you could feel it throughout the conversation. That freedom shows up in how she expresses herself post-White House: rocking her natural hair (she shared that she stopped relaxing it a while ago) and even wearing braids!
Mrs. Obama also referenced the CROWN Act and made her stance clear: if we’re wearing it — whether it’s a fro, locs, weaves, or whatever, and getting the job done (oftentimes exceedingly well), then the hairstyle is appropriate. Point blank. Leave us alone!
Lastly, I’ll leave you with her fashion ethos, the message she sends to herself every time she gets dressed. Whatever she puts on has to feel good as much as it looks good. When she slips it on, looks in the mirror, and says, “Damn, that’s bad,” then she knows it’s a winner!
She’s also not one to chase trends. For her, it’s about amplifying designers she believes in and showing up authentically, always as Michelle. I always say, when you look good, you feel good.
I love this new era she’s in. I’ve admired her style for as long as I’ve been aware of her, and having Tracee host just made sense. You could tell they’re Girlfriends 😉 IRL, the conversation flowed effortlessly, and the sisterhood was real.
I decided to remix the look I wore to see her six years ago, this time adding one of my faves: a pair of Jordan 1s. Mrs. O reminded us that we should never feel bad for being stylish; fashion is meaningful. So slay on, in whatever way that means to you!
As a sports mom, cultural curator, and proud Belizean, Karese brings intention to every experience she creates. A multimedia producer and creative strategist, she’s dedicated to amplifying voices and stories that often go unheard. With over a decade of experience across media production, content development, and brand storytelling, her work lives at the intersection of culture, community, and confidence.
From producing heartfelt campaigns that celebrate Black women in sneaker culture to managing large-scale video projects for city agencies, Karese approaches every project with purpose and heart, helping women and girls of color feel seen, heard, and celebrated.
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