I get what you're saying about the "back of the closet thing," but I've always worn vintage clothes -- 50s bombshell style and early 70s hippie, in particular -- so, my clothes look as out of era now as they did then. There's obviously things I no longer have the body for, but in general I should be as able to put on this sort of shirt with dark jeans now as I could have then. It's more that when it was my norm, in an entire day I might get one "cool shirt" or "where do you find such random clothes?" Now, when I wear my shirt that's similar to that, I spend all day talking to people about it,

I think you're right, that it's mostly a confidence thing. If I'm able to be (and/or fake) confidence, it'll probably be easier to deal with the general sense of shock.

Well, if it's any consolation, if you're even thinking about it you're ahead of most people you see walking around.

Fake confidence is underrated. Just get out there and be who you want to be. If you dork it up once in a while, that's OK. One thing I've learned is that YOU will remember every painful second of every humiliation you ever suffer but other people probably won't -- so if you look down and realize, "Jesus, pink polka dots, what was I thinking", it's OK -- tomorrow's a new day. It's better to take a chance and fluff it than just give up trying.

The drawback to "50s bombshell", "70s hippie" etc. is that a specifically identifiable retro style can become just as confining a box as "mom jeans and sweatshirt". That's where mixing it up comes in.

If you get in the habit of thinking about your style dynamically, you will as an added benefit be better able to handle the transitions later as you get older. Classic style is important at every age. And you DON'T want to be one of those old ladies you see who shop at Claire's and dress like tweeners!

You're right. It's just that nothing used to get me more excited than going to an estate sale and weeding through all these gorgeous outfits that had been kept in trunks, completely unworn for decades.

I do have the classics, though. A little black dress in wool, a classic white shirt, a handful of skirts with nice silhouettes, two cashmere sweaters, three pairs of jeans that work, and a decent collection of flat and heeled shoes and boots. It's more that I only wear the classics, and never wear anything that feels like me.

God, I wouldn't shop at Claire's by the time I was 16, I promise I won't start now.

Your post hit a lot of the things I struggle with on the head. I'm not a mom, but I'm in my thirties now, and so I have to figure out what it means to dress like my early-thirties self. I find it particularly hard in terms of jewellery, accessories and makeup. I have historically loved dramatic, but now it all feels *so* dramatic

Word. Oh, and I forgot another style inspiration site you might like http://www.weardrobe.com/

I'm in my 30s, too, and have always liked 70s styles. As I get older, I'm more conscious of trying not to look like I'm wearing a costume. It's harder to pull off all vintage. Mixing a vintage blouse with modern pants like skinny jeans and some knee high boots is common way to pull off a more sophisticated yet still stylish look.

Have you checked out Topshop?

http://us.topshop.com/webapp/wcs/stores/servlet/TopCategoriesDisplay?storeId=13052&catalogId=33060

They have some really cute, quality clothes that are still affordable and age appropriate. I like their Swedish Summer lookbook.

Modcloth also seems like a good site, though I haven't bought anything from there. This super stylish blogger gets most of her clothes there, though, and she looks great:
http://www.theglamourai.com/

And this site links to some great style bloggers for inspiration:

http://www.glamour.com/young-and-posh

Dramatic jewelry, me too. The overall style thing that worked in my 20's and is all wrong for how I feel today, is my poverty mentality. I always risk ending up with a lot of little shit because it's not expensive; in clothes especially. So I have v little (nothing?) in the way of "signature' pieces that I can wear for several years. I am great at buying for events, so i have a goodly amount of fab wear once in a blue moon dresses and tops and then my non-profit who-cares I'm in Seattle look. That's clothing; I'm really happy in what I've achieved in the jewelry dept though! I no longer wear anything that could be deemed as costume or this-style-minute. Not saying that's a good thing in general, it's good for me. I spend a lot more money on just several earrings and necklaces that have that drama that I need and are very "me" and have nothing to do with what is or isn't in the stores right now. I can and do wear them anywhere. I love it. I am lucky that I prefer sterling to gold, so I think that's why the shift was more affordable! I would do it with gold too though, for example starting with one amazing not-small gold hoops, etc. I don't at all have the few staple fabulous shirts or pants though - the kind some women say they wear "anywhere" and dress up or down. Will check out the websites pronto, thanks Cedarthvader!

Once I nailed down my new style, I found a lot of what I needed at thrift stores, H&M, and Buffalo Exchange. So I didn't spend a ton.

may i call you cedarth for short :-) ? The 2nd and 3rd are too young for me (can't believe I'm old enough to say shit like that, but there it is). Went through a short period when I resesnted and resisted that fact, but now it's just not my taste. The more time passes the more I I want well tailored clothes and quality materials. A couple of tops or a dress that is 'right now' is great, but beyond that I want the really good stuff, like my favorite: a perfectly tailored, smoothest light weight merino wool, all season blazer/jacket by Armani. In any case, it's less about where do I shop and more about continued learning about what looks good on me NOW, which isn't what it was 10 years ago. Like the original poster, the whole idea of style. The best specific advice I've received about clothing, which would not have occured to me on my own, is to use a tailor with all your clothes that "almost" fit,including jeans. Literally get a tailor made fit which will make every piece of clothing look flattering.

Oh, and I love thrift stores! A really cool little one I've discovered is in Bellevue called Heart to Home. Good selection but not overwhelming like Goodwill. Less vintage, but some. I bought this mint, faux fur calf length coat there- late 60'/early 70's?-for $25- yahoo!

@Virginia: Thanks for the store suggestions! First look through feels intimidating (think that's why I used to shop estate sales rather than modern stores), but I'll have another couple of drinks and go through them.

And yeah, I've generally paired 70s tops with modern jeans, at least partially because it's harder to find well cared for vintage pants that don't look ridiculous. Most of my 1950s styles are more full dresses that I pick up, so I usually would wear them as an outfit.

@Elle: Yeah, I resisted paying for tailoring for too long. Now, anything I get goes to my local seamstress. It helps that I live within walking distance of chinatown and little india in Toronto, so it's easier to get affordable tailoring when I want it.

I often get great jeans at thrift stores. I think I don't bother with the rest since it's so much work to wade through an entire Value Village or Goodwill to find the three things that look great (and were not, ever, what you came to hoping to find).

@Cedarthvader: Weardrobe is completely demoralizing. I found 5 outfits that I sort of could imagine wearing. Each outfit sent me to a list of similar pieces of clothing to look through. The first time, the only thing I liked was the $1124 sweater, although I would have been willing to try the $700 one as a sacrifice. The second one, I found a $600 single breasted jacket (apparently the type I should wear). Third, $425 jacket. Fourth, $535 tank top. Fifth, nothing on sale looked great.

I used to just buy an entire estate's worth of clothes for $500, get everything drycleaned, keep what I liked and then resold the rest to vintage shops. Nowadays I don't have the time or energy to do it, and I'm guessing I'd have more competition in Toronto than I did in the smaller town where I grew up. I'll try Buffalo Exchange and H&M. Never been in Buffalo Exchange, and only been to H&M in Switzerland in the 90s.