I'm not normally what you'd call a light packer. I always start with the best intentions, but at the last minute, I always decide I have to bring that extra pair of jeans/sweater/four pairs of shoes, and before you know it, my suitcase is stuffed. But in a little over a week, I'm going to this little conference in Chicago (anybody else going? Find me -- let's chat!), and I'm determined not to overpack. And I have a plan.
I purchased this dress at Old Navy (it's no longer available online, but it's at my local store in both short, which is shown, and long, which I also bought). It was $24.50, and I can make it work for just about anything with the proper accessories. Seriously.
For example, for the plane ride, I'll wear it with a cute (but functional) cardigan, flats, and probably pearls. Because, really, I'm willing to do just about whatever I can to keep security from treating me like a suspect, and who suspects the blonde in pearls and a cardigan? (FYI, I'm not planning to be guilty of anything -- I'm just paranoid about getting frisked.)
Then, for sessions/impromptu chats/cocktails, I'll be bringing my favorite bright scarf (it's wide enough to go over my shoulders for a bit of warmth, too). Worn with stylish, funky, but totally comfortable gladiator sandals and interesting earrings, I like to think I'll look interesting without seeming like I tried too hard. Because, guess what? This outfit is EASY!

Then, should I decide to tone it down a bit without giving up all my style, I'll pair it with some bold silver jewelry, a cute little clutch, and bright yellow heels. At least, for as long as I can walk in them. And I'm aware that this outfit won't work for something truly formal, but I very rarely go anywhere that requires me to be dressier than this.
Moral of the story -- whether it's a little black dress, your favorite jeans/sweater combo, or something else, if it makes you feel good, spend a little time trying out different accessories with that outfit to see if you can get some different looks out of it. And try it on. You never know -- two prints might really complement each other, and that belt might give your outfit a whole new appeal.
What kind of accessories do you use to get the most use out of your favorite clothes? Leave a comment, or if you're in Chicago, come and tell me all about it. I'll be the one at the bar trying to figure out how to make the cocktail swords into some unique jewelry so I can wear the same dress yet again. Oh, yeah. And I'll probably be wearing a navy dress.
In the meantime, you can read more from Kristen at jeez-o-petes.com.

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Great idea!
extremecommute July 13, 2009 - 10:57am
This is fantastic--like the "wear it 20 ways" magazine spreads, but more doable! I'm heading to South America for a few months, where it's winter--and because I'll be joining my old choir's tour, I'll need nicer clothes in addition to backpacking clothes. Now I'll be on the lookout for the cold-weather equivalent of your little blue dress...