How do I dress like a successful man who gets laid a lot...

This. It doesn't matter what you wear as long as you are decent looking and know how to talk to women. Women are attracted to confidence. Of course money and status plays into it but casual sex is easy as long as you can be moderately funny or charming without spilling your spaghetti and have your shit together.

Wear whatever style you're comfortable in, but get in shape. If you're fat, nothing will look good on you regardless of where you shop. If you're fit, everything will look good on you. Beyond that:
1. Wear clean clothes. Don't wear the same damn jeans everyday for two weeks without washing them.
2. Wear stuff that fits decently. You don't need to wear ultra tight jeans, especially since you'll look like a huge faggot in them, but wear something that's at least close to your size. Anything way too big or too small will look ridiculous.
3. Wear clothes that look like you bought them within the last year. Don't wear anything beat to shit, faded, or torn.
In other words, look like you at least give somewhat of a shit about yourself.

Also, women care a lot about shoes for some stupid reason. It's one of the first things they notice about your clothes. Nice shoes go a long way in women's eyes.

Wear pants.
Shirt optional
Shoes optional but nice to keep feet from getting soar when walking on rocks.
Also socks keep feet warm.
If it's one of those days, wear a hat.
If you like to know the time wear a watch.
If you have bad eyes glasses.
Also always wear sunglasses whenever possible because life is too short.
How is this even hard?

I prefer clothing-optional preschools, myself.

Your unwarranted self-importance is showing.

Rainbow flag cape and tie-dyed tightey whiteys. Bonus points for dragon dildo-tipped spear.

Did i leave my unnaturally-elongated turgid member hanging out of the bottom of my trousers again? Oh dear!

Oh yeah, also dress fly af

Literally the only correct answer