Dear shorts: I am so mad at you. Part 1.

F*cking shorts. What's the issue? Can we wear them? And why would we want to?

This is Shopping on Champagne. And she says “no short shorts after 50!”

I have this long history of issues around shorts. And as with so many other “clothing things” it’s so much more than “a clothing thing.” Sigh. Hence, this is a two parter. (You’ll get actual styling examples on Sunday/Monday if you’re subscribed — and lots of them!)

Let me go (briefly) back. I am not athletic. At all. Growing up, I had to be the captain picking the team or I’d definitely be picked, like second to last. Something about this is folded into the idea of shorts. I will get there.

I’m not athletic-cool. It often meant not participating in things. Things I might want to try — like the rope swing over the pond — and things I have NO INTEREST in — like the pickup whatever game. (In my youth I learned to be funny instead. Can you tell?)

And it’s also related to the idea of what’s been called “the tyranny of casual dressing” — like the notion of all those people on match.com “looking for a girl who’s just as comfortable in a baseball cap on Superbowl Sunday as blah blah blah.”

A real woman, about my age, wearing shorts beautifully IMHO while in the Design District

I’ve always viewed shorts as the key to the casual kingdom. “Are you coming on the boat?” (You’re wearing shorts.) “We’re putting up the volleyball net.” (You’re wearing shorts.) “Oh hey, someone’s all dressed up.” (You’re not wearing shorts.)

Only — some of us have trouble wearing shorts for a variety of reasons.

(1) Our fears about our bodies: Those of us who have ass/thigh aplenty, and maybe have finally come to appreciate or be ok with that (thank you, JLo et al) still may not want to put these assets on display in shorts. Especially short ones. (See also “Rosehip Jelly”) And note that even young, lithe

Becky Malinsky

puts a sweater around her waist sometimes, ok?!

(2) The shorts themselves: If you missed the Free People labia shorts hullabaloo (read the comments - you’re welcome), you’ll know that the shorts trending are … short.

(3) The dowdy potential: And even though Bermudas are happening too, they might feel too “on the nose” lady if you’re 40 or 50.

(4) The risk of feeling too try hard. I am very comfortable with my age. But I am NOT comfortable looking like I want to be something other than my age. Shorts put me at a high risk of feeling that way.

Yet suddenly, from a fashion/style perspective, the stakes are higher.

Once upon a time, it was relatively easy for me to avoid shorts. I found like one pair I thought were fine, and I stuck to those plus casual skirts like this from Von Sono. At 53, I know myself, and I know I don’t want to throw the ball around, thanks. I’ll stay here in my pareo reading a book while you enjoy that.

But back then, it used to be about looking casual, getting on the boat, etc. Looking like everyone else when in Maine. But now it’s about so much more.

Exhibit A:

Leandra Medine Cohen

. Showing us, regularly, that everything looks so good WITH SHORTS. Shorts DOOOO SOMETHINGGGGG.

Exhibit B: Prada SS/24.

It’s about FASHUN! And for that, I will not be sidelined.

What I think shorts do is really dial up friction. Unexpectedness. I can look at my IG feed and mentally swap out shorts for what I was wearing, and most of the time it’s a killer swap. Almost like Allison Bornstein’s “wrong shoe theory.” Denim shorts carry the most potential reward, the ultimate friction. I have certain pieces like a silky Raf for Dior top that I hang onto out of pure, unadulterated passion. And denim shorts are often the ONLY thing that makes them feel IRL wearable, especially in Miami where jeans are tough. But the same denim shorts also carry the most risk (it’s the try-hard thing!).

Ok first of all, you can wear whatever you want, however you want, at any age you want. And look amazing. That newsletter and its “jawns” notwithstanding. They are not the boss of us. Anything with some confidence looks good to me … and “to me” is totally unimportant - “to you” is.

That said, I did understand when a reader,

Lisa

asked me about wearing shorts after 50. Because these thoughts, the dowdy/try-hard concern, are especially vexing for those of a certain age. I mean, there are unique issues. I have a 21 year old son I’ll be in Greece with this summer. Even if I loved them and felt confident, I wouldn’t scar my kid for life just to wear micro shorts.

Over time in Miami, I have developed a shorts — WARDROBE! Yes, through hard work and perseverance, laughter, tears, despair and returns, I now have multiple pairs of shorts!

So here’s what I did for Lisa (and all of us!)

I tried on every single pair. And styled outfits. And thought about why they work. And in Part 2 of this newsletter, I’ll be sharing all the styled looks plus all the information you need to get those shorts and shop for others. From now on, you’ll only be on the sidelines if you prefer it that way. (I still mostly do. It’s where the coffee and snacks are.)

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