Let’s take a moment to look at the overall ugliness of some celebrity fashion choices. While I love seeing a classic or beautiful or modern look on the red carpet, sometimes it’s just fun to see something that flopped royally.
Here’s Chloe Sevigny in an oversized caftan-type gown that completely disguises all her curves and hangs on her like a blanket. On top of that, it’s pretty much see-through. So completely unsexy in so many ways.

Also, I have no idea what is going on with Charlotte Gainsbourg (left) in this picture. While that may be a baby bump, pairing it with some kind of romper dress (one of the most unflattering articles of clothing around) just makes it look like a disfiguring tumor.

And here’s Freida Pinto in what appears to be a metallic lamé robot dress. Her legs look great, but there is nothing else flattering about this.

If you watch the TV show Mad Men, you’re very familiar with January Jones’ brittle and put-upon character, Betty Draper, the 60s housewife trapped in a life she doesn’t want. But in real life, JJ appears to enjoy breaking out of her role and trying new things, fashion-wise. And sometimes getting panned by critics for it!
Critics mostly hated this blue dress she wore to the 2010 Emmy’s …one called it a “mullet dress”!

I personally don’t think it’s awful—there are many, many worse dresses out there. And there’s something fun about it. But I wouldn’t have chosen it for a red carpet event.
Apparently all that on-set 60s lingerie inspired JJ to break out this dress—which looks more like a corset that should be worn underneath a dress than a dress itself. Definitely not into this look, although her hair and makeup are actually really pretty.

And then she decided to go really daring in red Versace dress at the Golden Globes. While her hair has a classic 40s look, the dress is very modern—and leaves very little to the imagination.

But a few weeks later at the 2011 SAG awards, JJ was demurely covered.

No one can say that January Jones chooses boring dresses or always looks the same! What is your favorite of JJ’s looks?