Can somebody dress me please?

I’m not very good at dressing myself. Oh I’m fairly competent at pulling on pants and doing up my bra strap, but when it comes to picking clothes that actually look good on me and make me feel like a well-dressed, confident woman, I fall a little short in the skills department. I know what I like, but what I like and what looks good on my lumpy body are usually two different things. (Ah yes – if your psychoanalysis skills are intact, you’ve zeroed in on the problem – I’m not too fond of my overly-accentuated curves or my hang-to-the-waistline never-wear-button-up-tops boobs. So I avoid stores that remind me of that particular inadequacy. Sigh.)

I tend to dress for the lowest common denominator. 1.) Is it cheap? 2.) Does it fit? 3.) Is it a little less likely to make me look like a lumpy elephant or Dolly Parton’s saggy, less surgically modified twin than the other stuff on the rack? Lately, since we’ve been living with one income for most of the last 6 years (and kids grow out of clothes way too fast), number 1 criteria has trumped the others – it’s gotta be cheap. Approximately 75% of my clothes have come from second-hand stores, a fact that mortifies my fashion-conscious teenage daughter. (But it’s not all bad – I have lots of scarves collected from the various countries I’ve visited, so I almost always throw on a splash of colour to draw the eye away from the worn-out not-very-trendy threads underneath.)

Now I find myself in a dilemma. As you might have guessed, this “communicator of the year” thing is kind of a big deal for me – a career milestone, you might say. They’re going to present me with the award at a schwanky “gala luncheon” in a fancy hotel ballroom. This is the kind of place that will be filled with confident, accomplished business people, mostly dressed in power suits and shiny shoes. I don’t think many of them will show up in the shoes they just bought for $5.99 at Value Village (they’re great shoes, by the way!), or the blazer that has the sleeves rolled up to cover the hole in the cuff.

Since this kind of thing doesn’t happen every day, and I want to make the most of my “moment in the sun”, I want to treat myself to some new threads that make me feel good and look at least a little like what you'd expect the "communicator of the year" to look like. No, I don’t want to dress like them (I’m not a power suit and high heels kinda gal), I just want something that suits me and makes me look smart and feel confident (though still unique and a little bit funky).

So…. HELP! I need a personal shopper! I am SO not good at buying clothes for myself! I don’t even know where to begin. Usually I just rush into a store when I need something, grab whatever fits my lowest-common-denominator criteria, and rush out again (or stop for cheesecake if I find nothing and the shopping experience made me miserable – go ahead and psychoanalyze!) I wandered around at lunch time yesterday, and the racks of clothes just sort of overwhelmed me. I don’t know what colours look good on me (with the exception of turquoise – EVERYBODY always tells me I look good in turquoise), I don’t know what’s a good style for my body type, I don’t know where to shop, and I don’t know how to match tops with bottoms.

Anybody have any advice? Or a free Saturday afternoon to drag me to a store and pick something out for me?