I'm 25, but nearly all my life treated/dressed like a boy (not choice, poor family relied on hand downs) but as I got older I still dressed like a tomboy as this is what was 'normal' for me. I have relationships where I obviously want to look a little sexier at times, but feel REALLY uncomfortable with dresses/make up. I feel I look hideous if I try! I'm not ugly, nor fat, just not into change!
I don't want to be like this.
I don't want to be like this.
Seriously. You sound just like me. :O
I am much like a tomboy and my appearance is not very feminine. I'm not overweight, and from what I understand I am not unattractive. I know exactly what you mean about not being into change. While my outlook has changed to a 'degree' my dress code has not. And I feel like a moron when I try.
In my opinion make-up does constitute femininity but you don't need it to look feminine and you shouldn't wear it unless you absolutely need to. Like for dress-ups and special occasions; it can be nice, but it is still not needed. The only time I wear it is when I Masquerade.
Having clean clear skin is better than make-up and is always more attractive {to me}. However, wearing a little bit of lip-gloss and slightly tinted cheeks and eyelids is acceptable in most cases. Layering your face with make-up has two downsides.
[1] you have to touch up all day.
[2] it's not good for your skin.
If you do decide to start wearing it make sure it is all organic.
One thing I have learned is that you don't need to wear dresses to look more feminine. A lot of the times you can express sexuality through fabrics and you can get the same effect as you would if you let it all hangout.
Try tender/romantic looking blouses with unique cuts and details, ones that expose your back, short sleeves, puffy sleeves and classy looking V-necks. Make sure they are softer colors like pastels or bright colors that make you skin tone pop. As I mentioned before, fabric and texture makes all the difference. Like cashmere and chiffon or anything that has a flowing effect. I like the way silk feels but it does not look as nice as it feels most of the time. As for other details, I like lace and prints around sleeves and collars. Beads and sequins are okay sometimes as long as they don't look too juvenile. Oh! And button up tops with pretty buttons go a long way to making you look feminine, and are simple enough to not make you feel uncomfortable. These blouses don't have to be over the top either, they can look very simple.
Jeans are good. As long as you have the right cut and fit you'll look nice. I hate back pocket details because I feel like it will draw attention to my bum cheeks and I don't like it when people look at me. But if you like if you don't feel that way you should buy jeans with details. Leggings and stockings are fun and girly you should wear them with dresses.
Jewelry is another option. Bangle bracelets, necklaces and earrings can make a plain T-shirt and jeans look feminine. Any accessories can have this effect like belts purses and shoes. If you are not feeling up to some of the other suggestions, then I think accessories are your best bet.
I also think it would be best for you to start out with subtle changes. Change a few things at a time. As you get more used to it you, it will come more naturally. Don't force or you won't like it and you might give up all together.
You could cut your hair or try going to a salon. I know when I get a hair cut I feel more willing to change other aspects of my appearance but I never do. Maybe you would, though.
I feel like I got of topic, so I'm going to stop now. :}
I don't like wearing dresses other than for special occasions.
I am in love with jeggings. You could try those if you'd like. I think they make me look more feminine and if you have the right body type they'd probably look good on you too. I honestly think I can wear any type of top and look feminine if I'm wearing jeggings or skinny jeans. You might not like shoes with heels, but you could try regular sandals with heels or sandals with designs and whatnot.
I don't like wearing makeup all the time but I'll either use mascara, eyeliner, &/or eyeshadow. I love eyeshadow because it doesn't take long to put on (although I'm probably not putting it on right XP) and it comes in any color you can think of.
Accessories go a long way. You could wear a watch, or a bracelet or necklace. Earrings also, I love hoop earrings. I actually only own one or two of each type of jewelry. XD
If you want to start dressing with more frilly or "girly" stuff, go for it! But first, be sure you really want it. Do it if you like it better, not just because you think your gender requires it.