There’s a Red Dress in My Cart I Can’t Justify. It Took Me Eight Weeks to See Why.
There are certain tabs on my laptop that get closed the minute they’ve done their job. Airline schedules. The ten-day forecast. A recipe for something involving eight steps and a mandoline that I am never, ever going to make.
And then there’s the red dress.
It’s a red linen shirtdress from Apiece Apart. It costs $485 which is more than I have spent on a dress in a very long time, and I have closed that tab four separate times with tremendous conviction. It reopens. Some mornings I make coffee, and there it is, waiting in the corner of the screen like a cat that has decided which chair is now hers.
I finally figured out why last week. But I have to start with a form.
And if you came here for the practical half—how to wear a shirtdress in fall without buying one single thing—it’s below, all five of them. Short version: you don’t change the dress. You change what’s around it.
In this Post
The Box at the Bottom
My fiftieth high school reunion is at the end of August. Omaha. Same town, same people, fifty years later.
The committee sent a bio form in June. Name. Then. Now. And down at the bottom, a little box asking me to sum up fifty years in two hundred words.
It took me three days.
Two hundred words. I have written grocery lists longer than that. And yet every version I typed read like a resume handed to somebody who’d asked for a photograph.
Three sons. Ten years of this blog, which began with one outfit photo, Mr. Style behind the camera, and not the first clue what we were doing. Losing him. Becoming BeBe, which rearranged something in me I’d assumed was set for good. A novel I started, set down for the better part of a decade, and finally sent out into the world this year. Losing Oscar, my German Shepherd, who walked me through most of the above and never once asked what I was going to do next. An apartment in Atlanta. A third grandbaby in September.
Two hundred words. It doesn’t even cover the dog.
I typed a version. Deleted it. Typed another one and deleted that too.
Because the box isn’t really asking what you’ve done. It’s asking who you are now. And I’ve been trying to answer that here every single day for ten years, so believe me, I know how slippery it is.
So I did what I always do when a question gets too big for me. I quit writing and went to work on the other half of that weekend—the half I actually know how to do.
Because a reunion isn’t just a form. It’s four days in Omaha. Fly in Thursday night. Friday afternoon free. Friday night, cocktails at the Empire Room. Saturday, the school tour and lunch at Big Fred’s. Saturday night, dinner at the Marriott Regency. Fly home Sunday.
That free Friday afternoon already has plans. I’m going to drive around, look at a few addresses, and find out which ones are still standing. Call it a stroll down memory lane if you like. I’d call it reconnaissance.
Pizza at noon and a hotel ballroom at seven is not one outfit, no matter how badly I’d like it to be. Four occasions, six outfits counting the travel days, one suitcase. Somebody has to decide what goes in it, and at that particular moment it was either the closet or another hour of watching the cursor blink.
So I started pulling dresses.
Five Dresses on a Bed
The black poplin with the tweed jacket. Old reliable. This dress has never once let me down, and it has never once asked for credit.
The black-and-tan floral. Sleeveless, a print the size of a dinner plate, so loud it does all the talking so I don’t have to.
The denim midi. Which isn’t really a decision. Denim is what I reach for on the mornings I don’t want to make one.
The pale blue linen. I pulled it out, looked at it, and put it right back. Ten seconds, maybe. Couldn’t have told you why. Hang onto that.
And the red one. The tab that won’t close.
Five dresses laid across the foot of the bed. I stood there long enough that Ollie came in to see what all the fuss was about, decided it didn’t concern her, and left.
SHOP THE FIVE DRESSES
- Talbots Black Poplin Shirtdress
- Maggy London Floral Shirtdress
- Ralph Lauren Denim Shirtdress
- J.McLaughlin Mary Linen in Stripe
- Apiece Apart Red Linen Wrap Shirtdress
Then It Hit Me
Black. Black and tan. Red. The denim, which doesn’t count, because denim never counts. And one pale blue dress I’d already put back without knowing why.
Westside High School colors are red and black.
Eight weeks. Eight weeks of circling red and black and it never crossed my mind. Nobody asked me to. There’s no theme on the invitation, no color scheme, no committee chairwoman calling to say “Wear your school colors, Beth.” Some part of me that hasn’t had a vote since 1976 has been running this entire operation without so much as a memo.
The blue dress is lovely. It’s just not ours.
And it’s the one I put back first.
I sat down on the edge of the bed. On a Tuesday. In the middle of the workday, with a deadline waiting downstairs and a laptop still open to a dress I keep not buying.
Two things came out of that. The first is that I am nowhere near as deliberate as I’ve been telling myself. Ask me in June how I’d choose a dress for that weekend and I’d have given you a very sensible answer about venue and dress code and what photographs well. Wrong. Something older had already decided and simply hadn’t bothered to inform me.
The second is the useful one, and it’s why we’re here.
Every dress on that bed was the same dress. Collar. Buttons. A waist. It’s the shape I’ve worn since 1976, and I have no plans to give it up now.
And every single one of them keeps right on working when the weather turns.
That part isn’t sentiment. That’s construction. Which brings us to the practical half, because it is ninety-four degrees in Georgia this morning and every store I walked into last week was selling wool. Hello Nordstrom Anniversary Sale!
Quick Overview
A shirtdress carries into fall with layering and accessories—no new dress required. Start with the fastest change: swap raffia or espadrille shoes for leather boots or loafers, then move the bag and belt to leather too. Add a jacket over the top, wear it open as a duster, or knot a silk scarf at the collar. Cotton poplin, denim, and structured linen all work into autumn. Sheer weaves and pale voiles don’t—though how long a lighter linen lasts depends on your climate more than the calendar.
Why a Shirtdress Works in Fall
Most summer dresses put up a fight in September. A shirtdress doesn’t, and it isn’t luck. It’s how the thing is built.
Collar. Buttons. A waist.
The collar gives a scarf or a turtleneck somewhere to live instead of somewhere to fight. The button front means you can wear it closed, half open, or flung all the way open as a layer. And the waist means anything you pile on top still has a place to cinch.
Three things most dresses simply don’t have. A sundress will only ever be a sundress with a cardigan thrown over it, and we all know exactly what that looks like.
5 Ways to Wear a Shirtdress in Fall
Roughly in the order you’ll need them.
1. Change Your Shoes—Then the Bag, Then the Belt
If you do one thing, do this one. Trade the raffia, canvas, and espadrille for leather or suede.
The Denim Shirtdress from Ralph Lauren reads high summer with those espadrille wedges. Put a flat brown boot on and it’s the second week of October. Same dress. Same everything. Texture announces the season before color gets a word in—your eye reads raffia as summer and suede as fall in about half a second, without consulting you.
Then keep going, because the shoes can’t do it alone. A wicker handbag will hold an outfit in August no matter what else you’ve changed. It’s stubborn that way. Swap to a structured leather bag, add a leather belt at the waist, and the picnic dress goes out to dinner.
SHOP THE LOOK
- Ralph Lauren Denim Shirtdress
- Beaded Necklace
- Wedge Sandals
- Wicker Hobo Basket Bag
- Suede Riding Boots
- Suede Shoulder Bag
- Buckle Leather Belt
2. Add a Jacket
The obvious one. Also the one that buys you the most weeks, so let’s not hold the obviousness against it.
Tweed. A blazer. A chore coat. Denim. The Talbots Black Shirtdress is cotton poplin, which means it’s perfectly happy on its own at ninety degrees. Then the tweed goes over it at six o’clock, and you’re dressed for the evening without a trip home.
Keep the jacket cropped or hip length. A long one over a midi swallows you whole. And on the days a jacket is more than the weather deserves, a lightweight sweater knotted over the shoulders does the same job for half the commitment.
SHOP THE LOOK
- Talbots Black Poplin Shirtdress
- Gold Hoop Earrings
- Gold Hinged Cuff
- Eisenhower Tweed Jacket
- Lightweight Crewneck Cardigan
- Kitten Heel Slingback
Now onto the Frank & Eileen Rory with a cognac leather wrap belt at the waist and espadrilles. The belt gave it a waist, and the brown leather did the rest.
✨ Beth’s Style Tip: Your leathers don’t have to match, but they do have to get along. Cognac with brown. Black with black. Cognac and black in the same outfit is how an outfit starts looking accidental.
3. Wear It Open, Like a Duster
Unbutton the whole thing and wear it as a layer over jeans or trousers.
I know. It sounds like something that works beautifully on somebody else. It works on all of us—but only with the right dress, and this is where most people go wrong.
You want a simple one. No waist seam, no tie belt, no pleating. Something straight and soft that hangs from the shoulder and keeps hanging once it’s open, like the Frank & Eileen Rory. Longer is better than shorter. Cotton and linen drape. Stiff poplin just stands there like a sandwich board.
Same dress you just saw belted a few paragraphs up. That’s the entire argument for this shape in one photograph—closed and belted, it’s a dress; open over jeans, it’s a light third layer, and I didn’t buy a thing in between.
Here’s what won’t work, and I say this with affection: my Ralph Lauren denim shirtdress is hopeless at it. That pleated waist has a firm opinion about where your middle is, and the second you unbutton the dress, the opinion is still there with nothing to do. Same goes for anything with a tie belt or a seamed waist. Those dresses are built to close. Let them.
Underneath: a fitted tee and a straight-leg jean or trouser. That’s the whole thing.
✨ Beth’s Style Tip: Keep everything underneath one shade darker than the dress. The eye reads it as a column, and the open dress reads as a coat instead of an accident.
SHOP THE LOOK
4. Knot a Silk Scarf at the Neck
The one that costs nothing, because you already own three of them and they are sitting in a drawer as we speak.
The collar was built for this. Fold a square scarf into a bias strip, tie it once at the base of the throat, and let the ends disappear down inside the placket. Or loop a long one and let it hang past the buttons—better on a midi, and it does the same thing a necklace does without the weight of one.
Silk while it’s still warm. Wool once it actually turns. And on the mornings you can’t be bothered with either, knot it around the handle of your bag and call the whole thing done.
SHOP THE LOOK
5. Change the Colors Around It
Fall is a color story before it’s ever a fabric story, and this is where most of us overspend.
Camel. Rust. Olive. Chocolate. Oxblood. Accessories in those tones do more seasonal work than fabric weight ever will. It’s the reason a linen dress in a strong color often reads more like fall than a cotton one in pale blue.
And some prints never needed the help. The Maggy London is black and tan, which is a year-round palette that has simply been pretending to be a summer one. Put a loafer under it, pop a lightweight cardigan on top, and it goes straight through fall.
Which brings us back around to the red one. The Red Linen Wrap Shirtdress from Apiece Apart is technically a summer linen. Put a leopard shoe under it, and it’s late-September, no argument.
Red and leopard sounds like a lot and looks like a decision. The leopard picks up the brown and gold that red always wants next to it, and it does the work a plain black shoe simply won’t. Add a brown leather bag, and you’re finished.
✨ Beth’s Style Tip: Leopard is a neutral. It has been a neutral since Diana Vreeland said so, then Jenna Lyons confirmed it years later, and I have no interest in relitigating it. Treat it the way you’d treat camel—it goes with more than you think, and it counts as your one interesting thing, so don’t pile another on top of it.
Not that any of this is why I want the dress. But it is a reason, and some days a reason is enough.
SHOP THE LOOK
- Apiece Apart Red Linen Wrap Shirtdress
- Maggy London Floral Shirtdress
- Gold Hoop Earrings
- Thin Gold Hoop Earrings
- Leopard Flats
- Leopard Kitten Heels
- Brown Leather Bag
Which Shirtdresses Work in Fall
These carry through anywhere:
- Cotton poplin. Holds its shape in humidity and takes a jacket beautifully.
- Denim and chambray. The most seasonless fabric you own, hands down.
- Structured linen. Not the gauzy kind. The kind with some body to it, especially in a strong color.
- Corduroy, flannel, and plaid. Real fall fabrics, if you’re buying new.
And these depend entirely on where you live:
The lighter linens. The Mary Linen in Stripe from J.McLaughlin is pale blue, thin, and above the knee.
Down here we’re running in the eighties straight through September. I’ll wear that dress right past Labor Day—loafer instead of a sandal, a cardigan for the restaurant air conditioning—and nobody in Athens will bat an eye.
And before anyone hands the whole Midwest a wool sweater on September first: I grew up in Nebraska. Plenty of Septembers out there are still shirtsleeves, and it’s October that finally turns. Even New England gets an Indian summer that makes a liar out of the calendar.
Which is the part nobody mentions about fall dressing. The calendar is national. The weather is emphatically not. Most of what you’ll read this month was written by somebody dressing for a forecast that has nothing to do with yours, so take the fabric rules and then go look at your own ten-day.
The ones that genuinely don’t make it anywhere: sheer anything, white eyelet, and cotton voile in a pastel. Those are July, and they know it.
If you’d like this outfit-by-outfit instead, here are seven transitional looks and seven late-summer dresses that go right into September.
Shop the Shirtdresses
- Talbots Black Poplin Shirtdress
- Ralph Lauren Denim Shirtdress
- Maggy London Floral Shirtdress
- Apiece Apart Red Linen Wrap Shirtdress
- J.McLaughlin Mary Linen in Stripe
- Frank & Eileen Rory Shirtdress
Shop More Shirtdresses
Tan in an easy midi. Warm neutrals are the quiet trick of early fall. This one looks like September weeks before the weather has agreed to anything.
Blue and white pinstripe poplin. The crispest version of the shape, and poplin takes a jacket beautifully.
Frequently Asked Questions
Can you wear a shirtdress in fall?
Yes. It’s one of the easiest summer pieces to carry into fall. The collar, the button front, and the waist all give you somewhere to layer. Change the shoes, add something over or under, and switch your accessories to leather and warm tones.
What do you wear under a shirtdress in cold weather?
A fine-gauge turtleneck, a long-sleeve tee, or a thin bodysuit all layer cleanly without pulling at the buttons. Add opaque tights and a boot as it gets colder. Skip bulky knits, which make the front gap.
What shoes do you wear with a shirtdress in the fall?
Ankle boots, knee boots, loafers, and suede flats. Trading raffia or espadrille shoes for leather or suede is the quickest way to move a shirtdress from summer to fall, because texture reads as season faster than color does.
Can you wear a linen shirtdress in the fall?
Yes, and how long depends on your climate more than the calendar. Structured linen in a warm or strong color works into October almost anywhere with leather accessories and a closed shoe. Lighter, paler linens hold through September across much of the country—the South, the Midwest, and anywhere that gets an Indian summer—and only go into storage early in genuinely cool regions. Weight, color, and your own forecast matter more than the fiber or the date.
How do you wear a shirtdress over pants?
Unbutton it all the way and wear it open over straight-leg trousers or jeans with a fitted tee underneath. Choose a simple, unstructured shirtdress with no waist seam, tie belt, or pleating—a dress built to close won’t hang correctly once it’s open. Keep what’s under it slim so the dress reads as a layer.
Closing Thoughts
Five changes. One dress. Four months of wear out of something already hanging in your closet.
That’s the whole argument for a shirtdress, and it’s why I’ve kept one in rotation since the seventies. It isn’t a perfect dress. Show me a perfect dress. It just takes direction better than anything else I own.
As for the red one, I’ve quit arguing with myself. Red isn’t a quiet color, and that is precisely why I want it. Fifty years is long enough to have earned being seen from clear across a room.
And it seems some part of me settled that back in 1976 and has been standing there ever since, arms folded, waiting for me to catch up.
Grit & Glammers, two questions. Do you remember your high school colors—and would you wear them? And which of the five are you actually going to try? I’m betting most of you skip the duster. Prove me wrong.
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