Pablo's guide to straddling the line between a tool and an asshole edit disclaimer: this guide leans towards asshole
1) Wear a belt that matches your jeans, and wear a belt that matches what you're wearing with your jeans. Don't wear a polished leather belt with a t-shirt, and don't tuck a dress/fancy button-down into your jeans under the age of 30. You may tuck a button-down in if your jeans fit you perfectly and you have a great ass, granted the button-down is appropriate for the belt and you're in a semi-formal situation where you can't not wear a button-down. I love love love love Lucky Brand Jeans and nobody makes better belts to fit than them, at the price range. Note, their prices are high, catch 'em on a clearance. I think their price range is perfect if you can afford it, because anything more is generally a waste of money, anything less may not get you a quality, quality pair. 2) Better have jeans slightly longer than shorter, but the width should be perfect. Don't compromise size, ever, you will always look stupid with or without a belt. You can always do a cool and presently-trendy roll-up of the bottom of your jeans if they're long-- bonus points to show off the selvedge sewing if your jeans are selvedge denim. I roll up all my jeans at the bottom cause they look cooler that way and I can make them fit the length of my leg perfectly, and this show off shoes a little more too, which I arguably value the most in an outfit. 3) Dark wash unless you're hot, trendy, and hipster enough to wear light wash. 4) Absoutely zero rips/tears unless you're on the set of Sons of Anarchy, you've sold your soul to Hollister, or you wear your jeans explicitly to build orphanages in the jungle. 5) OK to buy slightly faded/worn-ish jeans especially if they're dark wash otherwise you'll look like Steve Jobs. Not to be confused with destroyed/torn jeans. Don't be Steve Jobs, but don't be the neighborhood crackhead either. 6) ... Freezer thing? 7) Wash your jeans folded inside-out to avoid unintential fade. But wash your jeans. 8) ...........Freezer thing?
Edit notes: 9) Don't be afraid of button-up flies, they're edit: not sexy, but not weird either. They're only weird if you make them weird. Lucky Brand Jeans has a hilarious habit of sewing the words "Lucky You" vertically down the length of the fly where the buttons are. If a friend decides to go down on you, you take the hilarious risk of getting a great laugh or a slap in the face.