Yesterday morning, Word Raccoon insisted on wearing a dress.

I reminded her that we’re currently on foot. The totaled vehicle has not been replaced yet, though the search has begun. Ugh. 

She gave me that look. You know the one. The “I’m made of poetry and rebellion” one. She said she didn’t care.

Fine, I said. It was too early to argue. But she’d have to make do with sensible shoes, and I wasn’t letting her freeze; leggings were non-negotiable. It was going to be in the 60s when we reached the café, and I was absolutely sitting outdoors.

She acquiesced. (Grudgingly. With a dramatic sigh.)

But then she bargained.

And I, softhearted sucker that I am, agreed to wear the cowboy hat.

This should have its own decision tree, frankly, but that’s another post. And once you have it on you’re stuck unless you’re cool with hat hair all day. 

So there I was: dress, leggings, cowboy hat. And wouldn’t you know it? A guy going into the café said, “You look just like Reba McEntire!”

(Spoiler: I do not. Not even a little. Not my face, not my hair color, not at all. But thank you, Stranger.)

He said I just needed a guitar and to sit outdoors and sing.

I did not tell him:
A) I do sing.
B) I play a (very) little guitar. You know I mean I play a little bit of music, not that I play a tiny guitar, right?
C) I was already sitting outside.

Later, at the gym, a young man was singing loudly and enthusiastically, though almost entirely off-key. I think it was rap?? So calling it singing might be a stretch. It was…oddly charming. A kind of public karaoke confidence. I respect it. Even if his fun verbal doodles did remind me of bicycles. IDK why…the way they spun? 

Anyway, the point is: sometimes the dress wins. Sometimes Word Raccoon wins. And sometimes you just want a flowchart to help make the call.

So here you go.

Should I Wear a Dress Today? A (Mostly) Functional Flowchart 

Step 1: Do you want to wear a dress?

• Yes → Wear it.
  
• No → Don’t. That’s it. End of flow. Go live your pants or shorts truth. (Or skorts, but that’s just a confused garment if you ask me. Shorts? Skirt? Both? Make up your mind, oh piece of clothing!)
  

Step 2: Are you leaving the house?

• Yes → Do you want to make a statement?
  
  • Yes → Dress it is.
    
  • No → Consider your top-tier stealth outfit. Preferably all black. 

• No → Is a delivery expected?
  
  • Yes → Lounge pants or pajama shorts. Preferably the ones with the koala on them. BTW, where did they go? Word Raccoon!!
    
  • No → Night gown. You’re royalty now. Although is a night gown really a dress? Probably not. And if someone comes to the door unexpectedly, you will not answer the door in that. Pinkie swear?? 

It is one thing to wear your robe over your clothes on your sun porch for comfort and color. We do not wear our night gown (or robe, for that matter) when we are out and about. Are you listening, Word Raccoon? Word Raccoon??? Naturally, she is now at the top of the stairs in my blue night gown, hands in the air. Take that off before you trip, WR!  

Step 3: Weather? (I feel like you already know this, but just in case…)

• Warm → Dresses win: breeze = built-in AC. Curses on cute sundresses because you will be forever battling the “but these bra straps are so cute can’t I get by with displaying them because hiding them is next to impossible anyway but oh no. That’s so tacky. But who would even know it’s not a tank? But I know.” 

• Windy → Proceed with caution. Ditto crossing street vents. When I was in Paris last, I pulled a Marilyn but thankfully with just my blouse.  (And here I thought I’d never tell that story.) 

• Cold → Add tights, boots, blanket scarf, etc. And, if you’re me today, even though it’s July, add a small throw because when you bring your cape, people say you have a blanket anyway. Might as well oblige them.
  
• Rainy → Do you curse when you come home dragging wet material like a stray dog begging for a meal? Then not today. Or just  be sure to make it a shorter one if you do wear one, love.
  

Step 4: Will you need to climb/squat/perform chair and possibly table moving maneuvers?

• Yes → How agile is that hem?
  
• No → Proceed to twirling test. Administer by spinning thrice in both directions. You should have the sensation of wanting to squeal “Whee!” If not, it is not the dress for today.
  

Step 5: Is this outfit about being seen?

• Yes → Turn it up. Channel main character energy. But what about those times when you hope you were seen by the world but just aren’t sure? Hey, feeling cute beats feeling not regardless.
  
• No → Wear the dress you love and act like no one else exists. P.S. If you love it, everyone will ask you where you bought it. If you hate it, it will become invisible and rightly so. Also, why are you wearing a dress you hate, sweetie? Life is too short.
  

Step 6: Do you own a cowboy hat? (Word Raccoon made me add this!) 

• Yes → Is today the day it gets worn?
  
  • Yes → Saddle up, Reba.
    
  • No → Save it for your next crisis of identity. Or the next time it comes back in fashion because aren’t you a couple of years off, babe? Not that we pay attention to that much. If you have style, you’re always in style. Or so says Word Raccoon. 

• No → It’s never too late

TL;DR:

If Word Raccoon wants the dress, you’re wearing the dress.
If someone says you look like Reba, smile and sip your iced tea.
If an off-key man serenades the gym, consider it ambiance.
If you need a flowchart to make your choices feel sacred or at least well considered: here it is.

You’re welcome.

And Word Raccoon is a bit disappointed that only the stranger mentioned her hat. Next time she’ll try wearing a traffic cone atop her head. You know, for stopping traffic. 

Or maybe she’ll just hand out comment cards instead: How would you rate today’s ensemble? That could be entertaining. Or embarrassing. Or just very on-brand for WR.