Hi E.,
I love dressing up, and I always pay attention to what I wear even if I am home all day with my son. I used to get my nails done every two weeks and wear high heels everyday, but since I had him I can't really do that anymore (well I guess I could but it would be horribly inefficient and painful!)
So basically I just wear jeans, t-shirts, and sweaters most of the time with flat shoes. However, I choose a cute fitted graphic tee over a baggy sportswear t-shirt all the time. Likewise, I choose a pretty cardigan or pullover sweater (all washable!!) instead of a typical hoodie, or look for a semi-casual hoodie in a lightweight jersey. For jeans, I really like fitted wide leg--there are lots of great jeans at Kohls department store that are not expensive at all. Otherwise I find that H&M carries wide leg jeans for $40--also not that bad, but definitely more of a splurge if you are on a budget like me. I also have been wearing skinny jeans--they look great with a longer fitted tee or with a babydoll top. Forever 21 has great skinny jeans for ~$14 a pair. Kohls and Forever 21 also have really great sweaters that are comfortable, washable, hip, and pretty (and not to expensive!). I buy a lot of tee's at Forever 21 and H&M. I usually shop sales, and I almost always find great deals on everything. I'll shop the sales at J. Jill to find beautiful stuff that is not old lady, but also not to teenagerish. I try to stay away from stuff that is too trendy--no glitter or trendy skulls- because although I'm still pretty young, I don't want to look like a teenager. I find shoes all over the place, online, at Target, everywhere. I love little booties--super comfortable and super hot with skinny jeans. Blowfish and Rocketdog usually have super cute shoes for pretty cheap. I really like mary janes with wide leg jeans, or ballet flats. I try to find cute shoes with kitten heels (very, very, very low high heels) to feel a little sexy. I also have a few pairs of mid-calf or knee high boots. Essentially, I wear jeans or cargo pants, t-shirts, and sweaters everyday, and I almost always feel like I look fancy but not in a too fancy way, and I am always comfortable! I wear lots of skirts and dresses with tights and legwarmers too, even in winter, I just wear boots instead of ballet flats.
Basically you just have to find a style that you like and explore ways to make it work for you. Look through a few magazines and find pictures of clothes you like, or looks you like. Then go through your closet and see what you already have that may be dressed up, or dressed down to get the look you want. Then go shopping to find a few things you can wear on an everyday basis that fit really well and are comfortable and washable. Second had stores are a great way to go for accessories like scarves, necklaces, etc. Even just adding a necklace and a great belt to an otherwise plain outfit can give you an instant updated look! Then you can add other items slowly. I let myself but one or two new things a month. Get outside your comfort zone and try on things that you would "never" wear. They just may look great on you! Remember that the style you had prior to kid life is not you anymore!
Sorry this is so long. I really like clothes. I feel so much better when I think I look nice, and I think it's awesome that you are taking care of yourself and defining yourself outside of being a mother!
M.
P.S. Cute or sexy underwear is also an instant was to feel way better about yourself :)