Slay the grey with fashion
Photo credit: Anna Shvets

How To Slay While Grey: An Old Maid’s Guide to Breaking the Ridiculous Rules of Fashion After 50

So there I was, standing in a dressing room — you know, one with the fluorescent lighting that makes everyone look like they’ve been living underground for six months, when it hit me. The saleswoman had just cheerfully directed me to the “women’s department” after I’d been browsing the general clothing section.

The women’s department. As if I’d somehow graduated from being a person who wears cool clothes to being a “woman” who needs special clothing accommodation.

Here’s the thing about fashion after 50: We’re apparently supposed to disappear into a sea of beige cardigans and “flattering” tunics that could double as camping tents.

The Great Fashion Conspiracy

Why? Basically, they want us to disappear.

Somewhere along the way, society decided that hitting the big 5-0 means you automatically lose your right to stand out or draw attention to yourself. Don’t wear anything fun, fitted, or (heaven forbid) trendy. You’re supposed to embrace the “age-appropriate” uniform of shapeless tops, elastic waistbands (not that I’m hating on them), and colors that wouldn’t look out of place in a retirement home cafeteria.

The fashion industry seems to think that once we hit menopause, we also lose our eyesight, our sense of style, and our ability to look in a mirror. Hence the proliferation of clothes that seem designed by someone who’s never actually seen a woman over 50, much less walked in our shoes.

Breaking News: We Still Have Bodies (And Opinions About Them)

Your body might have changed, but that doesn’t mean it’s broken. It just means you need to get reacquainted with it — like running into an old friend who got a new haircut.

Maybe your waist isn’t where it used to be. Maybe your arms have developed their own little jiggle dance. Maybe you’ve discovered that certain bras are now more engineering feat than undergarment.

So what?

The secret to great style after 50 isn’t hiding — it’s highlighting what works now.

That blazer that makes you feel like you could run a Fortune 500 company? Wear it with jeans and sneakers. Those earrings that make you smile every time you see them in the mirror? Perfect with everything. The dress that fits you like it was custom-made? It doesn’t matter if it’s “trendy” or not. Feeling comfortable in your clothes boosts your confidence at any age.

The Real Rules of Fashion After 50

Forget everything you’ve been told about “age-appropriate” dressing. Here are the only rules that actually matter:

If it makes you feel confident, wear it. This includes (but is not limited to) bright colors, patterns that aren’t “slimming,” and yes, even crop tops if that’s your thing. Life’s too short to dress like you’re apologizing for existing.

Comfort and style aren’t mutually exclusive. You can look amazing AND be able to move without cutting off circulation. Revolutionary concept, I know.

Your style should evolve, not disappear. Maybe you’re not wearing the same things you wore at 25 (thank goodness — have you seen photos from the early 2000s?). But that doesn’t mean you have to dress like you’ve given up on joy.

Top Online Shops

I took a completely unscientific poll of online shops that friends my age are liking these days and these are their top picks.

Quince: Their tagline is “Luxury essentials, honestly priced” — I can get on board with that! Shop everything from shorts to dresses to bags and bedding. Just be careful, it can be easy to fall into the beige trap here.

M.M. La Fleur: For business and business casual digs, my gal pal Heather (she’ll love that) recommends this site for clean lines, inclusive sizing, and a fun but very wearable color range. Like Heather herself, this shop is on the pricey side, but will stay with you for a lifetime.

Halara: Once you get past the annoying assault of pop-ups, Halara offers affordable comfort for every aspect of your life, from fitness to office to going out for chili burgers. The key is (I told you I have nothing against them) stretchy waistbands. That means jeans you can actually have a sit-down meal in and not walk away with a button imprint on your belly.

Reformation: With a focus on sustainable fashion, Reformation offers bold style and quality materials that won’t destroy the planet you’ll wear them on. Mix a fun and sassy top from here with some Halara slacks and you’re golden from work desk to turntable.

The Bottom Line (Pun Intended)

Fashion after 50 isn’t about hiding your ass or following someone else’s rulebook — it’s about writing your own. It’s about walking into that room and owning it, whether you’re wearing a power suit or your favorite vintage band t-shirt.

Because here’s the truth: We’re not invisible. We’re not past our prime. We’re not supposed to fade into the background wearing sensible shoes and neutral tones.

We’re just getting started.

And we’re going to look fabulous doing it.

Let us know if you have any additional fab-50 fashion rules in the comments. 💃

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