advice from karl lagerfeld greatly appreciated

now that I've come to terms with being a grown-up and all, I start to realise maybe the reason I feel a little less than sprightly is because I dont dress like a grown-up. I know that sounds ridiculous, like who'd-wanna-dress-like-a-grown-up, but I mean it in a different way.

At the moment, most of the time I wear sneakers and running tights (as leggings) with a little skirt and tshirt/jumper as I walk to work and back each day (at work I wear a uniform). This is brilliant at 7.15am as I dont have to think about it or worry as the only people that see me is the guy in 7/11 as I buy my Up-n-Go and the dudes at work, who are all dressed the same anyway.

Where this falls apart is after work, when at least 2 out of 5 nights I end up in the city, either shopping, drinking, having coffee or equivalent with friends. Here I feel underdressed, messy, too casual, and inappropriate for most cafes, let alone most bars.

What I'm looking for is an outfit I can walk in easily, that with only a change of shoes can be suitable for post-work activities, including drinks. Obviously anything too dressy will require another outfit (and prior notice).

What also worries me is that this seems to have spilled over into other days as well. Those damn running leggings are just so bloody comfortable. In fact I'm wearing them right now. With a tshirt. And a cardigan. And my slippers. But I am at home, alone, with a cup of tea, so its ok.

Am I afraid to dress up? To overdress? I dont think so- my business hours style is almost the complete opposite. The uniform consists of a suit- high waisted pencil skirt, shirt, jacket. I always wear heels, unless I know I will be walking/standing for a long time. When I go to work for shows, I always wear the same sort of dressy stuff, and heels. So why the disparity? Am I compensating for one with the other? Do I have no middle ground?

In an effort to help this today I went to American Apparel. I bought a pair of dark metallic silver leggings (high waisted). Then on the walk home I bought a pair of clear heart shaped sunglasses. I love them both but as soon as I got home I realised the problem is that I have nothing to go over the leggings, and I dont want to wear them uncovered. So I SHOULD have bought a cute little high waisted ice-skating skirt. But this doesnt solve the problem.

I need to think of outfits I would not hesitate to wear to the Hairy Canary at 6pm that I could also pair with sneakers in the morning. Doesnt really matter how ridiculous that looks, as long as I can walk in it (this excludes pencil skirts and usually jeans. Its 3 kilometers.)

I think my wardrobe consists of 2.5 elements: Extreme Casual, Extreme Dressy, and Corporate (.5) (dont have much of this, but enough to make it useless in either other category).

ugh I am tired of this now. to be continued..... hopefully the answer is shopping!