5 Things I Got Rid of From My Fall Wardrobe After a Summer Style Epiphany

And six things our writer will be wearing all season long, including the perfect cashmere sweater.

While packing for my annual August vacation in Cape Cod last month, something happened as I pulled my bathing suits out of the bottom drawer in my dresser. I did not reach for swimwear with “suck it in” ruching, underwires for lifting, or wonder materials for holding it all together, I grabbed a bunch of flimsy one-pieces and bikinis. Basically, bathing suits that all said the same thing: Screw it. Who wants to go swimming?

I’ve been going to Provincetown for nearly two decades, first with my now ex-wife, then with various lovers, partners, and friends ever since. While the community is no longer the “gay ghetto” that I so loved when I first got intro’d to the scene, it’s still full of some of the most beautiful men I’ve ever seen; none of whom would be looking at me unless they were coveting the caftan collection I’ve been amassing since the ‘80s.

As I loaded up the car, I took things even further and snatched up the “miracle” bathing suits (those exasperating, not-inexpensive one-pieces I’d purchased at various times in my life when I felt “too fat” for the beach) from my dresser drawer and exhaled a hearty hell no, as I dropped them into a garbage bag and tossed them in the bin on my way out of town. It felt great. I made a mental note: Upon return, I would do a real closet purge and forever free myself from this crap.

It was a sublime vacation. I drank copious cocktails, ate my weight in oysters, enjoyed ice cream and charcuterie plates nearly every day, and had not a care in the world. I had beach hair and a new smattering of freckles; my Andie Swim Mykonos one-piece (I have three of them), as well as an assortment of full-cut retro bikini bottoms and halter tops, and a towel passed for a wardrobe most days; barefoot bicycle rides and maybe some lip gloss, if I remembered. I never wanted this feeling to go away.

So once I returned home, I made good on the promise to take stock of my wardrobe and called a hard no on anything restrictive in my closet. In no way am I thin, but in no way am I suffering any more discomfort for fashion, for being attractive to men, or fantasy bargaining in which I pretend that I’m getting back to the much more physically-fit ideal I held for myself when I was pre-menopausal and walking about 10K steps a day in NYC.

I am now 56, upstate full-time, and have been in menopause since winter 2023. I’m in decent shape, but let’s lay it on the line, shall we? I’m currently carrying an extra ten pounds, sometimes I pee when I sneeze, my lower back tweaks on occasion, and I want to get into bed rubbing foot cream into my cracked heels by 10 (cough, 9) p.m. whenever possible. There is no room for spandex in this scenario.

Yes, I do want to be vaguely chic, but more importantly, I want to be entirely comfortable. Comfort makes me happy, and happy now wins every time I get dressed.

I applaud the younger set who have adopted body positivity to the nth degree. It would’ve been unheard of for my mother’s generation to leave the house looking anything less than slim, trim, and tucked in. But the youth in my universe have flat-out rejected these outdated notions of beauty. It’s time to take a page from their book and stop sucking in my stomach. It’s time to admit that I’ve been sucking in my stomach. 

So, without further ado, here is the list of the biggest closet offenders, the items that got the heave-ho immediately as I started culling the clothing. Fire sale. They had to go:

Tight Dresses 
I’m saying goodbye to bandage dresses à la Herve Leger, or any other skin-tight sheath that calls for living on air and water for a week ahead of wearing it. Thankfully, there were only a handful or so of these in my closet. I’ll admit, I semi-agonized over each one for a hot minute, recalling price tags, Barneys Warehouse sales, and the now-antiquated notion that every woman needs a ridiculously sexy dress for a big night out. My big night out, these days, is an evening when we make a dinner reservation for 8 p.m. Here was the Donna Karan bugle-beaded number that requires several different Spanx for an entirely smooth line; a dress that the designer personally selected for me at a charity fashion event. That was a fun night. Forget that dress.

High Heels
With these, I felt slightly less wasteful (though of course I donated the rest) because my son’s 26-year-old girlfriend has the same size foot as me, so I bagged up an enormous grouping of heels and boots for her. I also made both of us laugh by trying on some of them and then gripping the walls for dear life.

Short Skirts
Vagina-grazing mini-skirts and anything else that is just too damn short. This is relative to the wearer, of course, but for me, if it’s too short, I feel like an over-served party girl teetering around after one too many. The one exception: short skirts with knee- or thigh-high boots, but even then, with opaque tights. Think Edie Sedgwick, not Miley Cyrus. Keep an eye out for Stuart Weitzman sales, I got these for almost 70 percent off (notice: no heel). 

Skinny (or Flared) Jeans
Ultra-skinny jeans or super flared jeans with very fitted thigh and butt profiles. Maybe Cher is pulling this off? All I know is, I am not. I’m getting a yeast infection just thinking about it.

Belts 
Basically ALL BELTS. I mean, what’s the point?

All this purging isn’t to say that I’m going to spend the rest of my days in joggers and Birkenstocks, although as I write this, ahem… No, there are plenty of pretty, sexy clothes in my closet that I will be wearing this season (and many to come). Here is what is staying put in my closet:

Wrap Dresses 
Diane Von Furstenberg wrap dresses or similar styles. You cannot go wrong, budget-wise, with a Karina Dress, if you like this silhouette. So very flattering, so easy to pack, and great with boots or kitten heels, and tights for fall. 

Bootcut Jeans
Bootcut jeans with a tiny bit of stretch. I like 7 For All Mankind. Straight leg or wide leg also read as chic and comfortable. Nothing Mötley Crue, nothing Woodstock ’69.

Cotton Pants
A few pairs of drawstring slightly-slouchy pants from the organic cotton company Pact that still have some structure to them so I don’t look like I just got off a 24-shift at the hospital. I pair them with a smaller-sized, more fitted t-shirt. 

Black T-Shirts
I have enough black t-shirts to outfit an army of Johnny Cash fembots. I like them straight-cut, and a longer-length. They go with any of the aforementioned pants, and in all their simplicity, they somehow always make me feel put-together and chic. Pick your poison, as to your brand, for me, that’s Marine Layer, Lucky Brand, or this sort of no-nonsense brand, Duluth Trading Co., that makes a scoopneck t-shirt with sleeves that hit at the elbow that is very Audrey Hepburn, even for big-titty girls like me. And when I say black, I also mean navy. As I’ve aged, navy feels more flattering to my skin tone. You’ll see. 

Fancy-ish Tops
I can’t remember who turned me on to Tuckernuck (was it you, Kim France?) but this brand makes “fancy” tops that are not preposterous; too fancy and I cringe. Just a tiny bit of eyelet or a single ruffle and we’re cool. Make a note for when you need a refresh.

Cashmere Sweaters
Roomy delicious cashmere sweaters from Ryan Roche are my weakness. If you lean more towards an androgynous sweater vibe, check out Corridor, a menswear line that makes a yummy soft cardigan that feels almost like a tweed. While these are both on the pricier side, I’ve realized I don’t need a billion sweaters. If you buy well, you can wear a good knit indefinitely. I believe in spending more for one or two sweaters that I know I’ll wear for years, instead of fast fashion that splits a seam when I sneeze (and pee). 

You may call this “uniform dressing” and I’m okay with that. This capsule takes into account how I want to be: comfortable and still reasonably pulled together.

As I looked at the clothes amassed on my bed after I ruthlessly raided my closet, I saw many of my “bad patterns” again and again. Things I bought, maybe wore once or twice, then decided it wasn’t worth the hassle, or things that never really fit my body but fit some ideal of it in my brain. 

In no way do I want to shame women who like shapewear, but since September still reminds me of picking out outfits for “back to school,” I’m taking this opportunity to go deep in the closet and emerge victorious as I lighten my load. If I was a guy, I’d say I’m free-ballin’. Who’s joining me in letting it all hang out? 

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