Midlife Style Check: Why I’m Trading Trends for What Feels Good

I was sitting at a red light the other day, fighting the urge to eat the peanut butter cups melting in my purse, when a woman waiting to cross caught my eye. I zeroed in on her because her outfit was – individually and collectively - (and don’t come at me for saying this) hideous. Brown boxy-shaped crop top and darker brown baggy paperbag waist pants that were wide-leg and cropped. She finished it off with clunky gold sandals.  

It was an outfit that checked all my Oh Hell No boxes: 1) UPS-brown; 2) wide-leg, and 3) cropped. 

I don’t know about you, but I’ve always found the wide-leg-cropped-pants combo impossible to wear without looking…well…hideous, and don’t even get me started on brown everything. Brown = the color of blah.

Somehow she made that horrific outfit WORK. I couldn’t stop staring at her because she looked so good. It was as if an invisible force field of confidence and style vibrated around her, surrounded her, and radiated out from her.

Maybe it had something to do with her perfect posture. Perhaps that’s the secret to fashion and looking put together and a lot of life too. Keep your spine straight, keep your chin up, and that small shift in body language creates a big change in your mindset. When you feel that good, you’ll naturally believe you look that good too. 

I do know that such a change would not make a difference for me personally if I tried to pull off a similar outfit. Not that I would, because OMG, not on this petite but on the verge of being chunky body. Plus, I know my limits: Black, black…and more black mixed with an occasional splash of color when someone mentions yet again that I always wear black  - but nothing TOO bright.

The older I get, the more I find today’s clothing trends mostly baffling and wildly unattractive, particularly on my body. I don’t understand any of them, and if I’m being honest, I don’t even know what’s in style, nor do I care. (Age 15 to 40-something me would be appalled at hearing that. APPALLED!!!) 

I do have a few favorite trends I’ve never let go. One of them is overalls. Gosh, I love overalls! Especially the ones made from a stretchy, soft fabric. I’m also on board with the Grandma chic that seems to be a thing now: the thick, oversized eyeglasses, dowdy cardigans, and deliberately uncoordinated patterns. As for all the other trends out there? I simply couldn't care less. 

At the end of the day, I’ve realized that comfort and joy far outweigh the pressure to chase the “in” styles. My younger self would be annoyed at my disregard for the latest trends, but my older self feels a sense of freedom in dressing for myself rather than for the world. 

Whether you’re fully embracing your own version of "Grandma chic," sticking to your favorite staples, or just wearing whatever makes you feel good when you roll out of bed, I’d love to hear your take. So, tell me—has your relationship with fashion evolved as you reached midlife, or are you just as baffled and unbothered as I am?