A new game I play when I flip through the catalogs I receive is, "What do I want to look like now?"

Regarding clothes, I think I typically fall between a 5-7 on a scale of 1 being "couldn't care less" and 10 being "fashion is my life and I run a blog about it and go to Fashion Week on my own dime just because I care so much." This summer, I've been more of a 3, with my typical uniform being either workout clothes, this achingly practical swimsuit or flip flops and a Target Merona dress (I literally have four of these. When I'm feeling fancy I switch up the belts.) However, as I try to get my body back in shape and enter the tail end of my maternity leave I know I have to start putting myself together more and to that end I'm working on figuring out how I'm going to dress in the future.

The last two times I lost serious weight (the first was a general weight loss, the second was baby weight) I got really excited about putting on two specific types of outfits. The first were cocktail dresses that at the time I needed for the various  activities related to my own and friends' nuptials and the second was anything that made me feel good about my waist and stomach, like two-piece swimsuits and formfitting tee-shirts. I liked the way I looked but moreover with those clothes I was proving something to myself, getting over a self-consciousness and body dissatisfaction that had nagged me my whole life prior.

I aim to lose the weight and to fit in some of those dresses again (mostly because they're cute and I spent some money getting them tailored) but I also know I won't dress exactly the same way I used to. It's not like I was the epitome of young-cool-gal before I had kids but even still there are certain looks that I think will get pushed to the back of the closet: some shorter skirts, some higher heels, anything that requires a strapless bra. That's just not how I feel right now. Sometimes this feels liberating: "Who cares how I look?!" Other times this feels depressing. "Who cares how I look. I'm just a mom. Wah-wah."

I confess I do have a look in mind of how I want to dress in this new phase of life but it's kind of embarrassing to articulate it, but the image involves cute (but comfortable) jeans and ankle boots and cool flowy shirts. I am not confident I can pull this look off but I'll try. This summer has been my Summer of Kimono as I experiment with flowiness up top. I purchased the kimono you see in the photo from Anthropologie and have been wearing it cautiously all season, not sure if I'm really pulling it off or if I look stupid (see this post for my adventures in Anthropologie.)

Yesterday I went to the pool with my friend Julie while wearing the kimono. She tried it on and looked adorable in it which helped confirm my purchasing decision. I confessed my fashion insecurity to Julie and she said something along the lines of "What are you worried about, Claire? You have great style!"

Then I realized that I have officially entered the age where I'd rather be told I have good style than be told I am pretty. Style, more than being fashionable or trendy, to me means having a clothing point of view, a particular look that conveys a person's taste and personality. It means liking the way someone dresses without necessarily wanting to wear those particular clothes yourself. Pretty is something you can't help, like your height. You can't control how people see it. Like most women I lived my early life yearning to be conventionally attractive but was acutely aware of what kept me from being there. But now I'll happily take style instead. If I do have style (and the energy/means to work it), that means that admitting I'm not the same person I was when I was in my 20's and had no kids and dressing accordingly isn't necessarily a downer, it's just a new challenge that I can figure out.

(Full disclosure: I wrote this while wearing a pair of Steve's boxers, a soft tee shirt and a comfy sports bra, in case you want to know what stylish moms like me wear when they're off the clock.)