During the work week, getting dressed in the morning is fairly simple. I look through my closet of black and white, pick a few things, and I have an outfit— White blouse, black sweater, tweed skirt. Black and white dress, cardigan, tights. Easy. If I'm feeling particularly lazy, I wear a dress.
Dresses are great because they're a self-contained outfit. All you have to do is add shoes. And because you're "dressed up" people think you put in all this extra effort, when the truth is, you didn't even attempt matching a top to slacks because you were half-asleep.
When it come to the weekend though, I always have trouble getting dressed. Why is it so difficult to dress casually? There has to be a middle ground between looking like you just rolled out of bed and looking like you're headed to a meeting.
Shoes are the first problem. 90% of my shoes have at least a 3 inch heel, so aren't exactly conducive to weekend activities like laundry and grocery shopping. But if I put on sneakers, I just feel dumpy. And short.
A few years ago, I bought a pair of cowboy boots while visiting my friend in California, and they have become a staple of my weekend wardrobe. They are one of the most comfortable pair of shoes I own, but don't look ugly like most comfortable shoes tend to (ahem, Uggs and Crocs). They also have a slight heel, so I don't feel like a total shrimp.
I also wear brown a lot on the weekend. It just seems like a casual color to me. Instead of my black patent leather bag, I like to carry something brown or tan with enough space to hold a magazine or two, in case I find a sunny spot to read. I picked up this chestnut leather tote on sale about a month ago, and it's a real workhorse. It actually expands at the top to be even bigger!
The jacket is one of my most favorite pieces. It's made by an Italian company called Kiton, known for their men's suits. (I got it at Filene's basement for a fraction of its original price). Even though it's fitted, it never feels uncomfortable— a perfect weekend piece because it looks nice and feels nice, too. The cashmere tweed is so soft you would think you're snuggled in bed— which is exactly where I would spend my entire weekend, if it weren't for the lure of brunch . . .