Every morning, while I chow down on my Fibre One and Shredded Wheat (with skim milk), I get caught up on my favourite blogs. I don't always comment, but if I follow you, I read!
This morning, this article on Age Appropriateness caught my eye over on Sal's "Already Pretty". I thought about the questions she asked us to ask ourselves about the choices we make. As I'm now an old bag of 43 (hee!) who still likes to wear so-called "age inappropriate" items, these questions hit home.
Because today I wore thigh-high boots and a mini-skirt:

Do your friends and peers wear it, and wear it well?
Mini and thigh-high boots. No to the boots, but yes to the mini. I'm a more daring dresser than most of my friends, and I'm okay with that. If I saw someone dressed like this today, walking down the street, I would admire her outfit, regardless of her age.
If it’s outside what your age group normally wears, why do you want to wear it yourself? The boots especially are outside my age group, I think, but the mini probably is as well. I wanted thigh-high boots in general because I just love the look. It's very "out there" and I enjoy being a little (or a lot) different! Wearing a mini is me being defiant in the face of "No Mini-Skirts after 35" (take that, Stacy London!). I think it's good to have general style guidelines for age, but I think by now I know how to style myself so that I don't look like I'm trying too hard, or look sleazy. I hope! Ha!
Does it make you feel fabulous about your body? Why, yes, it does! I love my body - and I worked hard to get it (maintaining my 50 lb weight loss for 3.5 years now). I like how my bum looks in this mini, and I like how my legs look really long in these boots.
Where will you be wearing it? I wore them to work! And although my coworkers went "whoa!" they did agree that they were neither slutty nor costumey (the Dread Duo of Daring Dressing). I have worn the skirt a few times before to work (here, here and here), always with a dark, opaque tight. I'll be wearing the boots again, for sure, probably with a dress or with some skinny jeans.
Who will be there, and whose judgment are you considering? Well, my coworkers (and I just showed them off to some guy friends who arrived). The judgment question is interesting. I know I like to create a stir with my outfits. I enjoy messing a bit with people's perceptions. Do I care what people think of how I look? Yes, of course. Do I care THAT much if people think I look a little nutty? Nah, not really. However, if someone said something nasty to my face, sure, I'd be hurt - I don't want to look BAD...just a little eccentric (like my friend, Steph, The Dashing Eccentric - yes, I'm just throwing that in there because she's given me a few shout-outs and I think she's marvellous).
Anyway, I felt good in this, and I felt ME in this. And that's what counts.

They're Pegabo which according to this site isn't made anymore, but I bought them at Feet First, which is owned by Aldo, who also acquired Pegabo. Looks like they are resurrecting the brand. Huzzah! And it's a Canadian company. Love it. They are suede uppers and leather inside, but I have to say: they stink! Whatever glue they've used on these is stinky-stinky. I'm going to have to stuff some dryer sheets in them and put them on the deck overnight to detox them.
I had two criteria for thigh-high boots:
1. No pirate boots. No fold-over flap at the top. No higher front than back. No laces at the back of the calf (a buckle would be okay, though). No pointy toe. I've had pirate boots before (c. 1989) and loved them. They were purple suede and they got ruined at a GWAR concert when I had some fake bodily fluids sprayed on them, but that's another story. *ahem*
2. No hooker boots. No "Pretty Woman" boots. No shiny. No uber-high heels or hidden platforms. No crazy colour, something neutral but not black.
After dragging my niece to most of the downtown shoe stores, I found these. My heart raced. They met all my criteria!

The other stuff:

Blouse (Nicole Beniste for Point Zero), vest (Le Chateau, gift from Ruth), skirt (Jacob, consignment), boots (Pegabo), green necklace (Mom's, vintage), other necklace (Plum).