I really wish you'd post a picture of yourself. I'm not a man, but all of my clients are, so maybe my post can help. In my line of work, it's important for me to look my best.
You said that you look like a clown or drag-queen when you apply make-up? Well, the important thing to remember is that cosmetics are meant to enhance your appearance, not mask it.
~If you're going to use foundation, mix it with a good moisturizer. That will make it thinner and easier to spread, and will help keep you from accidentally using too much.
~When using eye shadow, keep it simple until you really know what you're doing. Even something close to your skin color, but slightly lighter or darker, can make a big difference.
~Use lipstick/lip gloss that is clear or close to the color of your lips.
~Most people don't actually need blush, or don't need much of it. You could probably skip that and look fine.
If you're normally a tomboy, you probably aren't going to be comfortable in skirts and heels. I recommend wearing nice dress pants. In the summer, you could get a skort (shorts made to look like a skirt). You could wear flat dress shoes or a pump. One of my favorite pairs of shoes is a boot that goes to my ankle. It has a thick sturdy heel that makes me feel safe, but lifts me about two inches.
Monochrome (all one color) outfits are more flattering than multiple colors, and dark colors are usually more attractive than light. You could use a pretty necklace and bracelet to brighten it up, and by changing accessories, you can make an outfit look different the next time you wear it.
