Eyeliner and mascara is good enough. You can start light with brown and gold eyeshadow and concealer under the eyes. Also definitely use chapstick regularly; my boyfriend always comments about how soft my lips are. I do have other makeup tricks like add a little shimmery white eyeshadow at the inner corners of your eyes and always always apply moisturizer to your face in the morning (with SPF) and night. When you have good skin, there's little need for makeup.
As for fashion: check out a magazine or just browse online at sites like Pinterest. Then go to your closet and try to make an entire outfit with each item. Remember, even if you have really basic stuff like t-shirts, tanks, etc...ACCESSORIZING IS KEY! Personally if I'm feeling lazy, I just put on flashy earrings and suddenly I look more put together.
For shoes: switch it up. Try wedges, low heels, flats etc. I recommend Shoedazzle.com.
*I was also not a fussy dresser until recently when I got a boyfriend too haha.
A little black dress or a print summer dress from forever 21, asos, topshop, WeddingCountdown , shopbob etcwould be better for you, more than shirts and jeans, pants, covering all skin style. You need something like necklace, a tasteful ring, bracelet, earrings, not statement but very suitable for you. What's more, heels is needed to show your legs and adds beautiful elements to you. xoxo
have confidence! having confidence can really change the outlook people have on you , especially men. I would say choose your favorite feature and focus on that. If it's your eyes, use a complimentary eye shadow color to make your eyes stand out even more. If it's your waist , then incorporate belts into your outfits to put around the smallest part of your waist to define it more. Anything you like on your body, you can always find fun easy ways to enhance it !
Hmm, I don't know if you like heels, but maybe buy a unexpensive pair of kitten heels, or just very low heels (not too high!) and see if you like them. Heels instantly give you that "oomph" in my opinion... it makes you walk different, (learn how to walk with them first before going out in public though), they give you good posture, etc etc...
Maybe also try out some cute jewelry, think of pearl studs, or diamond studs, a nice simple ring, heart necklace, just very simple but cute jewelry! Nothing too over the top!
Maybe try out a different hair style too. Wear a ponytail, or wear your hair half up/half down, it's very cute and sophisticated looking.
i'm not really a girlie girl either but one day decided to surprise my boyfriend by wearing a skirt with tank top and cardigan when we hung out and he was SO excited about it. he LOVED it. I just don't feel comfortable wearing dresses and skirts that often but every once in a while I will and he really likes it. so I think you should try finding a skirt/dress you're comfortable in and wear that :). also maybe do a different hairstyle once in a while? I usually just wear my hair which is curly/wavy down but whenever I straighten it or put it in a ponytail or a nice bun, he really likes it.