I've been a long-time lurker, and I'm coming out of lurkdom because I really want to commit to figuring out my personal style and buying clothes that are appropriate. But, I am overwhelmed and have no idea where to start. I've done a closet clean-out, and I hardly have anything left, and I don't know how to get started on a new wardrobe. I'd love to hear from those of you who have gone from almost nothing to a full wardrobe of wearable clothes that you love.
A couple of my specific concerns:
1) Should I buy basics first and then build, or buy clothes that I really love but might not be wearable for more than a season? I typically try the second approach, but I then find myself with lots of random items that don't go together and don't even reflect me but just reflect a whim. I have lots of clothes, shoes, and jewelry that have gotten worn once or twice that I am later too embarrassed to wear. I would like to have a clear plan in place before I buy new clothes because I feel like I'm just wasting money when I wear something once or twice...or not at all.
2) Outfits or separates? I have a horrible time putting together interesting outfits, so I'm drawn to buying things that are put together online or in stores, but then I feel like I can only wear the shirt with the particular skirt that I bought it with...
3) Lifestyle - I'm a college professor (in the arts and humanities - definitely a dress-down profession), but I look really young for my age. For work, I tend to dress up most of the time because otherwise I look like I'm a student. Even when I'm wearing a full suit, I sometimes get asked if I'm a student. In any case, I'm more concerned about my casual wardrobe - non-teaching clothes are especially lacking in my closet.
4) Style - I would like to be trendy, modern, urban...but I'm just not. I'm drawn to classic, feminine shapes (no ruffles, but figure flattering shapes), but I tend toward looking boring and safe. I'd like to look more artistic and less like a conservative person on her way to brunch, since that really doesn't reflect my personality. Most of all, I have discovered that the clothes I wear again and again are the ones that are comfortable and easy. For me this means skirts and dresses in knits and cottons. (I'm an hourglass and have a hard time with fit sometimes, and I hate pants, shorts, and capris. I would love to never have to wear another pair of jeans ever.). But I don't want to be boring; nor do I want to stand out too much.
I'd love any and all advice!