Desperately seeking Jenna Lyons. I need your help

Dear Jenna Lyons:

After following your impressive career at J. Crew until you left in 2017, I was delighted to find your reality television show Styling With Jenna on HBO this past winter. I love your irreverent fashion sense and even though you’re over six feet tall and slim, which I most definitely am not, I try to tap into your styling savvy to create my own sense of je ne sais quois on a much more limited budget. I’ll never have your confidence (or the body) to wear a bustier with a canary yellow blazer or flouncy skirts with sequins but I envy your fashion courage. Blue jeans and giant white shirts with bling? Even I can do that.

I may not be long and lean like you, but I still want to look great.
Look what you've done with that necklace. That's the kind of flair with accessories I would like to have.
You make casual chic look so effortless.

There is a very strong possibility that COVID restrictions could be relaxing or even ending before long and I’m now faced with a dilemma. It has been fifteen months since I have worn anything other than yoga or sweat pants and tee shirts. Dressing for real life and going out in public will be a major challenge and I need help getting into the groove again. Specifically, I would like you to audit the contents of my closet and help me figure out what to keep, what to toss, what works with what, and let’s bin what does not work.

We get so much conflicting and often bad advice. I would like to turn the ‘good’ items in my closet into better or ideally, BEST.

More importantly, how can I create new and born-again looks that convey the real, undiscovered me, or even the old me with a newer, edgier twist? It’s my goal to finally capture the look I’ve been aspiring to my entire life . . . before I die. I’m a 73-year-old baby boomer who despite a lifetime of trying, has never quite managed to achieve the level of sartorial splendour I envisioned for myself.

During my working years, I spent vast sums on Dress For Success suits and classy businesswear. Now that I’m retired, I’ve been concentrating on casual wear that is still classy but with an edge.

I’ve run the Eileen Fisher gauntlet and while I love her style, environmental ethics, and the quality of her clothing, on me it’s often a bit lumpy and plain. But I do have some lovely EF pieces which are flattering and I wear regularly.

Diane Keaton, another one of my fashion idols.

Much as I love Diane Keaton’s flair, I don’t have a waistline so all those wide belts on menswear pants and flared skirts with skinny sweaters just won’t work on me.

My closet is bursting with loads of lovely tops, pants, sweaters, jackets, shoes, bags, and jewelry that have been collecting dust. How can I shop my closet and come up with new and exciting combinations that paint me as a brave, fashion warrior from the boomer age group? We’re rule breakers from ‘way back.

It’s not as easy as it sounds.

Over the course of the COVID lockdowns (which have been much more strict in Canada than in the U.S., which is why we’ve had fewer deaths relative to our population), I’ve practically lost the art of carrying on a conversation, the art of socializing, the ability to know how to order in a restaurant, and any skills I had acquired over a lifetime of being socially involved. We’ve been socially isolated for so long we feel insecure.

I’m sure there’s something really great in there somewhere.

How will I present myself when I am reborn, post-COVID? What should I do with the items that cost more than I care to admit that are currently hanging in my closet? Time’s running out. And, I know I’m not alone in seeking help to rejoin the world, to be born again. Are you free? Let’s talk.

Your friend,

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2 years ago

Oh so true Lynda. I want to dress my “age” without being frumpy, but I want to be comfortable and chic!
perhaps too much too hope for as we re-emerge.