How I learned to love clothes and getting dressed

after a 3 decade long slump

The angle makes my face look very very long - oh well. Red skirt from Banana Republic, forgot where I got the shoes last year, T-shirt from COS, scarf and glasses from local shops

Somewhere in my mid-50s, my relationship with clothes transformed.

For much of my adult life, I felt ill-outfitted. Almost everything about clothing myself was a struggle, especially when a special occasion or speaking event reduced me to panic shopping, when I always bought the equivalent of a prom dress, something I’d never wear again.

Or I borrowed a friend’s clothes, which sometimes worked, sometimes didn’t. Wearing a borrowed St. John knitted ensemble to speak at a Junior League gig was a brilliant choice, not so much the suit I wore on Oprah -- looked awesome on my friend, looked so silly on me. I repeated that on a few more national TV shows and big stages, driving home the story I couldn’t dress myself.

Of course, clothes are a sticky complicated struggle for most women because hey there patriarchy and capitalism, thanks for making this utilitarian or creative act a big ding dang do, a snarl of judgment about how we look, how much we weigh, how we signal identity and class, whether we fit in or not.

Also many of us reject thinking about clothes as a way to be free and to some degree that was me. Screw thinking about we look!

We can also add to all that any clothing peccadillos. Mine are being hyper-sensitive to all sorts of fabrics (too stiff, too itchy, allergice to all wools), and anything fitted is NOT happening, especially after the pandemic years.

Then there are my environmental concerns that can have me debating, sometimes for weeks -- will I keep this item of clothing for years? How was it made? Will I really truly wear it?

But perhaps what complicated getting dressed for me the most is that I judged caring about clothes as shallow frippery, a waste of time: if I cared about fashion, I was not a feminist, not a serious person, and lord knows, I always wanted to be a serious person.

So yes, getting dressed was a big ball of tangled yuck for decades.

BUT HERE’S THE THING: STILL I DESIRED TO FEEL GOOD IN MY CLOTHES

Maybe it’s the patriarchy in m y head but I don’t think so. I realized a few years ago (probably more I have such a bad sense of time), to go into my closet and be excited to get dressed. To be invited to an event and think, “I know exactly what to wear.” To love getting packed for a trip instead of panicking.

As much as I wanted to believe clothes shouldn’t matter to me, when writing Why Bother? two things became clear to me:

1. Dressing was a problem I could solve because I wanted to, not because I had to.

2. Solving it was another way to be free from the deadening constraints of being a woman in this culture by exploring my desire.

3. I knew what I liked, and I knew who I was; I could dress the woman I had become.

Dressing myself could be fun, liberating, creative, whatever the heck I wanted it to be.

I’m still very much in the middle of this project. But more often these days, I can walk into my closet and get dressed with joy.

Here’s what helped me get there:

• I stopped fighting and judging what I wanted.

• I stopped letting the noise of my past (my family’s nickname for me was sumo!) and the culture determine my experience.

• I thought about what I like to wear and what feels good, and embraced that.

  

  Sweater from Alex Mills (not currently available in this color in long sleeves), t-shirt from Uniglo, pearls redesigned from my mom’s, jeans from Madewell, sandals from Tread Labs

I gave myself permission

To spend time thinking about what I wear. It’s taken some practice to let myself have fun on something I once deemed frivolous but I’m getting there.

I think about clothes strategically

Before, I either shopped out of desperation or bought something because I thought it was cute or “special.” Turns out, you need to be strategic about putting together a wardrobe, and you need to pay attention to what you like. What colors do you like? Styles? Fabrics? If you buy something new, what will it go with? How many things? And most of all: what will you actually wear?

I educate myself about how to put an outfit together

I watch videos on Instagram and think, “What do I like about that? Would I wear that? Where? When?”

People I like to learn from:

Alexandra Stedman

, Jennine Jacob, Style by Bec, Graham Street, and Roz.

I’m not good at selfies! The top is from Sezanne, shorts from One Quince, shoes from Cork Ease, and the necklace is a gift from my daughter.

I mediate my desire

Clothes can bring out my craving for a dopamine hit. Then it’s about getting, not building, a wardrobe. I put things in my shopping cart and wait a day or two, glancing back at my choices and picturing myself wearing them. Often, I don’t pull the trigger on the purchase.

I shop mostly online

At stores that have shown some environmental responsibility (it’s difficult to know how accurate this self-reporting is) and that I know fit me, because returns are a waste of carbon and some retailers dispose of the returned clothes. I like Everlane, Alex Mills, COS, Madewell (mostly for jeans), Uniglo, and Marks and Spencer. I wish I were a thrift shopper or someone who could troll Ebay for vintage finds, but I get overwhelmed very easily.

I am slowly embracing accessories

This one has been challenging for me because I find most jewelry uncomfortable but so many outfits work because of the accessories. I started with neck scarves and recently, I took my mom’s old rings and pearls, and had three necklaces made that I love.

I took two strands of my mother’s pearls and had the jewelry maker add a few freshwater pearls. Earrings from One Quince. Eyeglasses local. Gray hair all mine.

I’d love so much to hear how you feel about dressing yourself, what helps, what frustrates you, and what you do to find clothes you love. I feel like we could have a VERY juicy conversation about this.

Thanks for reading,

Jen