Clothes that act my age

I have a tough time dressing for school. I loovve dresses, but I am small and it is hard to find ones that fit without:
a) being for a teen
b) looking really cheap looking (because it was made for a teen)
c) being really short on me (I'm 5'5")
c) having an unnaturally high waist

Plus, I already do have a naturally high waist, so that is hard enough to work with already. I have begun to embrace it lately. I will never forget being in 8th grade, at the height of Guess? jeans popularity, and some rude girl in my chemistry class saying something about my brand new jeans looking high-waisted. Sigh. I was so happy when Mariah Carey invented the low rise (albeit six years later).

One of my "teen" dresses, attempting to pass for 30+ (it's using its friend's fake)

Does it work with the boots and tights? That was one of the main reasons I wanted OTK boots this season--to provide more leg coverage with dresses (plus it's freezing and windy here). [It is so hard to know where to look/smile when taking one of these self-portraits in a mirror].

Yea I feel better about this dress! I always have to wear another cami under it AND a slip because F21 dresses have that notoriously bad lining that goes wherever it wants.I was thinking about using navy or blue tights with this outfit instead of black since the flowers are blue and gold. Might give it some more zip.

What I'm wearing:
Dress: F21 ($18)
Belt: a ribbon from another F21 dress
Cami: Rodarte for Target ($7 on sale)
Half slip: Macy's
Tights: Wal-Mart ($5)
Boots: Steve Madden

The older I get, the weirder I feel shopping in Juniors-like sections. Talbots makes some really great skirts, but they don't fit me. JCrew still needs tailoring. My favorite jeans this year came from Hollister, of all places. Really expensive lines fit better (of course they do!) and I have had the best luck with wrap dresses a la DvF. In the past, I have also had extremely good luck with the Target guest designer lines, particularly Richard Choi (all time fave pieces), Anna Sui, and Jason Saunders--but not so much with their more recent lines. I was psyched about Marc Jacobs, but a lot of the stuff looked really young.

Anyway, what I wanted this post to be about is wearing dresses, etc. and making them not look too "young." I don't want to look old and dumpy, for sure, but I also don't want to look like I am trying too hard or that I want to be the age of the students I am teaching (18-22). No thanks! I want to look my age, only good. I am attempting to balance shorter lengths with tights, high boots, and other layers.Without tights, this dress looks bare.

Too much skin! Not exactly skanky, but it just totally doesn't work. I am still figuring out the best methods to wear what I have. I will post both things I think works and those that fail--mainly to remind myself not to wear it again.
More experimenting to come.