There’s no season that tempts me to break the rules quite like fall — and I come by the impulse honestly. I went back to Omaha this month, fifty years after I left it, and the trip turned into a long walk down memory lane, straight back to the woman who taught me every fashion rule I know: my mother. Some of those rules I still live by. But a good many of them — the ones that get trotted out every single autumn — are exactly the fall fashion rules I think are worth breaking after 50.
Key Takeaways
- The old “no white after Labor Day” rule is the first one to break — winter white, ivory, and cream are some of the most elegant colors you can wear in fall.
- “Dress your age” is the most outdated rule of all. After 50, dress for how you feel, not for a number.
- Shoes and handbags no longer need to match — a little contrast reads more modern.
- A few rules are still worth keeping: never skip lipstick, and never leave the house in wrinkles.
- The best style rule after 50 is the one you write for yourself.
What came back to me first wasn’t a dress or a label. It was back-to-school shopping.
In our house, back-to-school shopping wasn’t an errand — it was an event, and it took the better part of a day. We’d drive to Crossroads, the only mall in town back then, before Westroads came along and opened up closer to home. Crossroads had a Walgreens, and that Walgreens had a soda fountain — the old kind, where they’d dispense your Coke right at the counter — and my mother would order each of us a chocolate Coke. Such a treat. I usually held out for a hamburger and fries as well because that’s the best kind of lunch for a ten-year-old. Maybe a sixty-eight-year-old, too! Then, fortified, we’d hit the shops again and keep going until every last thing on the list had been ticked off.
I still remember the year — junior high — that I put together a pink mohair turtleneck and a wrap-around suede skirt entirely on my own. My mother’s face just about beamed. And beneath the pride, I suspect, was a quiet little congratulations — half for me, half for herself, both of us knowing she’d taught me well.
That harmony didn’t last, of course. High school is exactly when your fashion choices start to rebel against everything your mother holds dear. We had a couple of knock-down, drag-out fights over clothes, which I find genuinely comical now. Really? The two of us, going to the mat over an outfit?
Here’s what she never quite grasped in the heat of those standoffs: I hadn’t sworn off dresses. I still loved a good skirt, still reached for something pretty on a Friday night. I was simply ready to test the waters — to find out what else I might be beyond the girl in the wrap skirt she’d been so proud of. So I made room in my closet for overalls, corduroys, flannel shirts, and a pair of Vasque hiking boots I practically lived in. My mother, meanwhile, was certain I still belonged in a dress — or at the very least a skirt and a sweater, every day of the week. Neither of us gave an inch.
The irony isn’t lost on me. I put my mother through all of that — and then got off scot-free myself. My own children wore uniforms to school, which meant I was spared the closet-door standoffs entirely. Not once did I have to talk anyone out of an outfit before breakfast, or brace for whatever was waiting on the other side of a bedroom door. My mother, I’m quite sure, would have found the whole thing a little unfair.
What neither of us could see back then was that I wasn’t rejecting her taste so much as adding to it — keeping what I loved, trying on the rest. Which, come to think of it, is exactly what I’m still doing.
Fifty years later, fall still arrives with that same urge to refresh the closet. But these days I’m less interested in following my mother’s rules than in deciding which ones are worth breaking — because here’s what I’ve learned about fashion rules after 50: a few of them expired a long time ago. These are the ones I’m breaking this season, and the two I’d never give up.
The Fall Fashion Rules I’m Breaking After 50
Never wear white after Labor Day. This is the one every woman my age was raised on, and it’s the first to go. There’s nothing more elegant in October than winter white — a pair of ivory trousers, a cream sweater, an ivory tweed jacket, a camel sweater with a white tee peeking out. The trick is to let the fabric do the season’s work: swap summer linen and eyelet for wool, cashmere, and flannel, ground the look with a suede boot, and winter white suddenly looks like it belongs in fall, because it does. The rule was always more about the calendar than about looking good, and the calendar has never once told me what flatters me.
Always dress your age. The one I threw out entirely. I don’t dress my age — I dress how I feel, and most mornings that has very little to do with the number on my last birthday cake. “Dressing your age” is usually just code for shrinking, for reaching only for what’s expected. I’d rather reach for what I love — a good boot, a bold coat, a leather jacket, a lip in a color that wakes up my whole face — and let the number sort itself out. Fit and confidence read as more modern than any birthday ever will.
Always match your shoes to your handbag. I’ve let this one go. A bag and shoes no longer need to be a matched set the way they were in my mother’s day — a little contrast usually looks more modern anyway. I still love when a color echoes from the ground up — a cognac boot picking up the warmth of a chocolate bag — but matching for matching’s sake is a rule fall is far too interesting for.
A Few More Fall Rules Worth Breaking
The list doesn’t end with my mother’s. A few more that get repeated every autumn and deserve to be retired:
“You can’t wear black with brown.” Nonsense. A chocolate boot with black trousers, or a camel coat over black, is one of the richest combinations there is in cool weather. Fall is the season that rewards mixing your browns, blacks, and every shade of tobacco in between.
“Sneakers aren’t grown-up.” A clean white leather sneaker with tailored trousers or under a midi dress is polished, current, and a mercy on the feet when you’re on them all day. Grown-up is about how you wear a thing, not the thing itself.
“Skip bold color as you get older.” This one gets it exactly backward. A saturated coat — emerald, cobalt, a proper red — is the fastest way to look alive against a grey autumn sky. Neutrals are lovely, but color is not something you age out of.
The Two Rules I’d Never Break
Not every rule my mother handed me was made to be broken. A couple, she got exactly right.
Never leave the house without lipstick. Still guilty, and I doubt I’ll ever change. A swipe of color is the fastest thing I know to look pulled together, even on the mornings when nothing else has cooperated. She was right about that one. A few of my favorites:
Charlotte Tilbury Matte Revolution Walk of No Shame
Merit Signature Lip Millennial
L’Oréal Colour Riche Saucy Mauve
Never leave the house in wrinkles. Still gospel. A wrinkle is the one thing that can undo an otherwise beautiful outfit. I’ve only traded the ironing board for a steamer — five minutes, a little steam, and I’m out the door.
Yes. The no-white-after-Labor-Day rule is a leftover from another era and has nothing to do with what actually looks good. Winter white, ivory, and cream — especially in cozier fall fabrics like wool, cashmere, and suede — look fresh and modern well into the cooler months.
The ones rooted in fear rather than flattery: no white after Labor Day, “dress your age,” and matching your shoes to your handbag. None of them make you look better — they just make you look like you’re following instructions. Keep the rules that serve you and let the rest go.
The ones rooted in fear rather than flattery: no white after Labor Day, “dress your age,” and matching your shoes to your handbag. None of them make you look better — they just make you look like you’re following instructions. Keep the rules that serve you and let the rest go.
Stop dressing your age altogether and start dressing for how you feel. Reach for pieces you love — a sharp blazer, a good boot, a color that lifts your face — in shapes that fit your body now. Fit and confidence read as modern far more than any trend does.
No. A perfectly matched set can actually look dated. It’s more current to let them relate through color or tone rather than match exactly — think a cognac boot with a chocolate bag, or a black shoe with a burgundy clutch. But honestly? The right handbag can match perfectly with the right shoe and look modern and fresh.
Closing Thoughts
The truth is, the rules were never really the point. What my mother actually handed me, over all those Saturdays at Crossroads, was the idea that getting dressed is worth a little care. The rules that still fit, I’ve kept. The ones that stopped fitting, I’ve quietly let go. That’s the part she’d understand — even the rebellions.
Style has no expiration date — and neither do you.
Grit & Glammers, I want to hear yours: which fall fashion rule are you finally breaking this year?
Shop the Post
The pieces from today’s post, all in one place:
- Ivory wide-leg trousers
- Cream turtleneck sweater
- Ivory tweed jacket
- Cognac suede ankle boot
- Statement coat — emerald, cobalt, or red
- White leather sneaker
- Handheld clothes steamer
- My signature lipstick
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