So, ’tis the season - the season after the season, that is. ‘Tis the season of awards… and with it, the endless and impossibly subjective rating (and berating) of the Best and Worst Dressed.
I’ll start by saying I have an almost limitless appetite for red-carpet fashion. Glamour is my weakness and I’m fascinated to see the choices made by those with the means to pick and choose. But I have a very hard time with the notion of Best and Worst. It seems to me that the dresses most often picked as “best” are the safest ones, the strapless black sheaths and glowy satin gowns that would flatter a goat. They are lovely, surely, but hardly notable - revealing only that the wearer is competently able to sidestep disaster. It’s the fashion equivalent of knowing how to walk on a sidewalk. Meanwhile, the term “worst” is liberally showered on those who eschew mainstream aesthetic, who take a risk and opt for something more avant garde. If one were to apply those terms to office workers or politicians, perhaps I could see it - but it’s just stupid to talk about fashion that way.
So I seek the lists and devour the images, but find myself railing at the secretly-conservative critics who arbitrarily praise and pan. I think to myself, If I was in charge of that list…
In the Worst Dressed Category… Really?

Mad Men’s January Jones somehow made a Worst Dressed list in this fantastic bit of Versace. I have been staring at it for fifteen minutes trying to figure out where the problem is… Blue on a blonde is almost always striking. The dress is beautifully constructed, and the layer detailing on the front of the skirt is whimsical and flattering. It doesn’t look painted on, which is a nice change - and did anyone notice? There’s a pocket, for heaven’s sakes. Why can’t I ever find a formal gown with a pocket? Top the whole thing off with her Veronica Lake hair and those perfect red lips - the girl is a knockout.

To be honest, Renee Zellweger almost always surprises the hell out of me. She has such an open, friendly, down-home kind of thing happening, I never remember that she’s a total glamourpuss. Although this outfit by Carolina Herrera also made the Worst Dressed, I think it’s divine. It’s a surprising mix of Victorian prim, 40s Hollywood, and Nevada housewife. The simple gold cuffs and clutch are perfect accessories - and 20 points to our Bridget for knowing enough to keep the already highly detailed neckline clear of unnecessary jewellery. It’s a black dress and a classic line, but it’s far from boring. I’m not crazy about the hair, but I won’t go to the mats over it.

What can you say about Cameron Diaz? She’s seems friendly, she looks like she’d be fun to drink with, and she’s got a klutzy kind of charm that makes her appear completely guileless. She’s no fashion plate - but I’ve never gotten the impression she aspires to be one, so that’s that. On first glance I saw this gown by Chanel and thought it was a bit of a mess. The hem is all over the place, there’s some kind of random bow stuck halfway up the thigh, and the asymmetrical top looks like it might have started out as part of another dress altogether. But here’s the thing: It suits her perfectly. It’s adorable and a bit goofy, the neckline (once again, bare of accessories) is charmingly offbeat, the colour should be awful makes her skin glow, and the strange pleating on the bodice could only work on a girl with a boyish figure. Add to it her sweet, tousled hair and low key makeup, and she looks like a beautiful (possibly Swedish) child dressing up in a very pretty bedsheet. How on earth can that be bad?!

Okay, this is not the greatest outfit (designer unknown) I’ve ever seen. Fine, I admit it. But holy crap, people, Glenn Close is over 60 and what she’s wearing is dignified, the lines are clean, and it fits well. This outfit is, though slightly Golden Girls, completely age appropriate and impeccably tailored. 20 points to Glenda Veronica for sidestepping the Grandma’s Cleavage trap. On top of that, the woman is a force. Have you seen Damages? Talent is sexier than anything else. Get off her back.

Laura Dern is a funny duck. She always seems a bit awkward, as though she only just got fitted with a human body and hasn’t quite sussed out what to do with it. Her taste in earrings is dubious, clearly, and she needs to fire her hairdresser immediately. But what on earth is wrong with this dress? It’s fantastic - it’s got a delicate, vintage feel, and the detailing is both understated and complex. It suits her tall, slender figure and the length makes her ankles look damn sexy. Ms. Dern is never going to be a sex kitten - 20 points to her for not pretending to be (which is always a disaster). If this is “worst”, may we all be so lucky.
But this is what we’re calling Best… Right.

Gossip Girl’s Blake Lively made the Best Dressed list in Nina Ricci. Sorry, but (and I usually try to find the upside in everything) this is slightly appalling. It’s too clingy and way to small. (I’m pretty sure I can see the outline of her intestines.) Some dresses look great skin-tight, but there’s something about the fabric here that is (or at least appears) too flimsy to do the job. What’s more, in the battle of Breasts vs. Dress, I can’t tell who’s winning - but I know it’s not a fair fight.
Summing it Up
I’m really not a huge fan of categorizing Best and Worst. I would, for once, like to see the people who make their living doing it take more into account than the flavour of the moment. A great outfit has so much more to do with the person wearing it - do they look confident? Happy? Do they look like they’ve made an effort or tried something new? I adore people like Chloe Sevigny (always willing to take risks) and Isabella Rossellini (who exudes class and confidence from every pore) because they dress to please themselves and reveal part of their personality in doing it. The occasional disaster is a reasonable price to pay for aesthetic integrity. Besides - if you’re willing to get it really wrong, sometimes you’re bound to get it really right. That’s always better than playing it safe.
And now… the best for last…

Drew Barrymore in Galliano for Dior.
She’s had some judgement lapses in the past - but this more than atones.
Eight zillion points for getting it really really right.
Yowza.