I hit rock bottom this week and advised a colleague not to go gray. Here's what happened.
Several of us were traveling together back to Texas after a conference in the Washington, D.C. area. We got through security and had some time to kill, so we stopped at a restaurant for a glass of wine. I was counting the number of women with gray hair. Stylish Young Coworker was with us, and she was my scout.
SYC: Silver at 3 o'clock!
Me: Hate it.
SYC: The color is pretty.
Me: Haircut blows.
SYC: Silver incoming!
And so it went. Traveling companion #1 is in her mid-50s. She said she would like to go natural and embrace silver hair but has no style and thought it was better to keep the color. And I agreed! I said it's a package deal. If you aren't going to commit yourself to developing a cool style, stick with the dye. It's actually the low-maintenance solution for people who aren't into fashion.
Then we got to the style question. Why don't you care about style? Well, she said, my
feet are big and narrow. It's hard to find cute shoes. SYC and I are all
over that one. We'll help you find shoes. A flight attendant passed by
and I said, OK, over there ... that look is fine for them, it's their uniform. This is
not the look you are going for.

It's not?
This is bad. SYC asks if she has a flight attendant outfit in her wardrobe. Tell us, she demands, do you wear suits like that to work? Do you?
My good suit, she says, with a quiver in her voice.
What color?
Navy.
What color shoes?
Navy.
AHHHHHHHHH!
Then we get to the nude hose debate. As far as I am concerned, there
is never a reason to wear nude hose. Ever. SYC calls them sausage
casings. Nude fishnets are nice, I offer. Tights. Bare legs. Traveling companion #2 says her legs are too white for bare legs. Pale is nice, we tell her. You don't need fake tanned legs.
I can't believe I am dishing this advice. Just a few years ago, I would have thought the flight attendant look was acceptable. In a moment of weakness, I thank the vigilantly critical SYC for mentoring me through my style journey. If not for the grace of SYC, I would be the gray-haired woman in the navy blue suit with nude hose and sensible loafers.
They announced our flight, and we all looked at our boarding passes to see which zone we were in. I couldn't find my zone. SYC looked at my boarding pass and said, "You got upgraded to first class!" I think I screamed. Several people looked up. Oh my God! Oh my God! I felt like I had won the lottery. And they were boarding first class already! Like right now!
Bye!
SYC was among the last to board. I was lounging in my comfy and spacious first-class seat as she passed by struggling with her over-sized carry on. Some people just don't listen. I did the beauty queen wave, and she stopped in the aisle across from my seat. Looked me straight in the eye and said without explanation or fanfare, "I hope there's a fly in your salad."