from what you currently wear i am going to assume you are a pretty casual person. some clothes that are comfy and stylish and tend to run low on the price are leggings. which are both warm and close fit. babydoll shirts. these tend to be girly but i find them quite comfy. iz byer and candies are both great brands with a great selection of clothing. sweat pants can be cool if they are a light color and they have a great shirt with them. and they CANNOT be baggy sweat pants they have to be fitted.
another look that is in where i am is dark (preferably black) fitted jackets. I don't recommend baggy baggy shirts but i also don't recommend skin tight shirts. and don't have a ton of the same type of shirt in different colors. try to change it up. oh and on the pants thing it depends on if you want to enhance anything like your hips or thighs or what not. and different types look different
a straight or boot-cut leg. A straight leg falls straight from the hip to the hem; a boot cut flares slightly (to give jeans room to fit over boots). Both cuts are slimming and make you look taller and leaner. Avoid tapered legs, as they give an unbalanced silhouette and make hips and rear end look big.
Pick big pockets. The smaller the pockets, the larger your derriere will look. Choose jeans with pockets that nearly fill the space between the rise (the length of jean between your crotch and waistband) and the edges of your rear.
Stick to a dark wash. Dark denim jeans always look polished and are most flattering.
Try a low waist. In the past few years, waistbands have steadily lowered. While an ultra-low waist is better left to teenagers, jeans labeled "low waist" are actually flattering to women of all shapes and ages. Avoid jeans that come all the way up to your waist, as they make your lower half look pear-shaped.
Add some stretch. Jeans with a touch of Lycra or spandex are flattering because they hug your curves, and they're comfortable because they move with your body (instead of pulling or tugging).
also try this site
http://www.associatedcontent.com/article/385232/how_to_buy_jeans_for_my_body_type.html
but all in all if you don't feel comfortable in it DON"T WEAR IT
and you should take a friend or sibling or mom with you so you can have a second opinion on how things look
hoped this helped