I think my weakness is that I like classic items so much that even if I buy bolder pieces, I don't really wear them much. I want to be more "original" with my style, but am scared to wear more attention-getting pieces. And I work from home mostly, so I often feel like it's too much trouble to wear my nicer items when just going out and running errands, etc. One of my goals for fall is to make sure I am still dressing "up" a bit when I leave the house. It's too easy to fall into a totally casual routine and I'm tired of feeling blah.
NCshopper, you are not a mess. I've seen your closet and you have such cute things in there! Maybe you are feeling the end of summer blues? I often feel this way when transitioning from summer to fall, or from winter to spring. I feel like I'm tired of all my clothes for the current season (like right now) because they've been worn over and over again for the last several months. And I'm waiting very impatiently for fall to wear sweaters/tights/boots.
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"Good taste shouldn't have to cost anything extra." - Mickey Drexler
The holes in my wardrobe are different from season to season. Since we're heading into fall, I'll list those.
Basics- solid or printed, l/s and s/s t's that I can easily layer with other things
Skirts- I have tons of skirts for summer but only one or two for fall
Dresses
Shoes- I'm not exactly sure what the heck I've been wearing on my feet for the past few years, but I have about two pair of shoes that I deem acceptable for fall/winter
Blouses- Basically, the only tops I have for fall are sweaters, but many of them are cardigans and I love to layer. However, at the moment, I have nothing with which to layer them.
Tights and belts
And lynnie, I'm totally with you on the jewelry thing. I refuse to buy jewelry b/c I want to make all of my own. But I've been so busy with my day job and other freelancing projects that I've had zero time to make jewelry, so that's become a huge hole, which is awful, b/c jewelry is my favorite accessory.
My wardrobe weaknesses are similar to yours, atlgirl. I tend to buy more basics, plain tops and pants. I want to be more inventive and unique with my style, but I have a hard time justifying something that is either:
a. very memorable (can't wear it often)
b. very trendy (might only like it for one season)
So I often end up buying and wearing safe but somewhat boring clothes.
Another problem area is weekend wear. I have tons of work separates to mix and match, but when it comes to the weekend, I seem to have only ultra-casual stuff, and I still want to look cute! I tend to rely on my jeans every weekend because I can't wear them to work. But I want to come up with some more creative ideas.