My friend Pamela is a stylish woman. Every person who meets her knows she’s got it together: the perfectly fitted jeans, the right blend of colors, the classy, understated accessories, and of course, the killer shoes. John’s made no secret about liking her shoes– polished, pointy, and high heeled (read: sexy). What, my generic Birkenstocks don’t do it for you, honey? Yes, we’re back to my style problem. I suppose it’s time for an upgrade of sorts… descriptors like librarian, frumpy, grandma, and student can only flatter me for so long. The big 3-0 is coming around the corner, and you know, it might be nice to NOT be labeled a grandma. I’m going to give this fashion thing a bash. Lucky for me, Pamela is more than happy to take me under her wing (more shopping for her!).

I don’t know how I arrived where I am, but I think most people who know me will agree: one of my biggest problems is that I’m super cheap (not necessarily for other people but definitely for myself). I frankly don’t know why I’m so extreme, but I have this weird game I play where I try to spend as little as possible each day. If left to my own devices, I could very well live in a tree (as my father has chided). I know, it’s not as if John and I are struggling for basic survival. Still, I guess I always have this belief that money is more for saving (for emergencies, essentials, “good” uses) than for spending. I also have this irrational fear that amassing lots of material things will ultimately consume and destroy us. Yes, a bit overdramatic, but hey what do you expect, it’s a compulsion right? Simply said, I have issues about money. I think that’s why I loved Cary Tennis’ column the other day about the destination wedding, about how money sometimes makes us compromise our values. Anyway, my money issue is another discussion for another day…

So couple my inherent cheapness with my overall impatience and voila, I’m someone who hates shopping and hates fussing over “getting ready.” Well in the year of the dog, I’m trying a new approach. The theme this new year is learning and improving. There’s much to be done. I need to improve in the following areas: dressing, cooking, exercising, and reading/writing Chinese. A full list, eh? This is gonna take a lot of work.

So I’ve been under Pamela’s tutelage for a week now, and I’ve shopped more with her than I’ve shopped in the last two years combined. Four days of serious, solid shopping. A bit exhausting but I think I’m getting the hang of it. Apparently, I was doing my body type wrong. I’m short waist, long legs. And my biggest fashion crime has been wearing high-waisted stuff. I’m guessing that’s where I picked up the grandma descriptor… Now Pamela’s got me wearing low- or mid-riders. Poor lady. I resisted strongly at first (Low-riders = Britney Spears with her pelvic bone hanging out!). But four days of intense shopping later, I am a convert. I now have three new pairs of jeans. Pamela is pleased that I’m adopting her ways but I don’t think she’s fully convinced I’m on board for good. Perhaps fearful of regression, she has instructed me to immediately move my old pairs to the donate pile. You have no idea (or maybe you do) how much of my clothes didn’t pass the Pamela test. River of Hearts can expect a hefty bag of clothing soon.

John is thrilled Pamela is helping me. He says I should just do whatever she advises, because when else am I going to find someone with the knowledge AND the willingness to reform me. In other words, if not Pamela, who else is going to help my sorry, no-style ass. Surely, I’m a difficult case study.

And damn, who knew shopping was such a process. Pamela knows when all the big seasonal sales are. She knows where the seams are supposed to fall on the shoulders, where the pant cuff is supposed to fall on your boots. She knows you have to hit a store several times even if it’s the same sale because all kinds of stuff emerge from storage when items on the floor clear out. Who the hell knew?