Golden Rules

1. No pleats or tapered legs

   You’re not a rock star, so no tapered or tight-legged jeans. Pleats are best left for your father to wear. Cowboys: your pants go over your boots - don’t ever stuff pants into a boot or shoe.

2. Make sure your pants fit

   A simple formula:

   1. Wear your pants 2-3 inches below your bellybutton. NO higher than that (unless you’re at a Steve Urkel appreciation party.) Also NO lower than that - you’re not a gangsta, and no one wants to see your underwear. Waist-size wise, seeing your butt is good, seeing your ass-crack is not good.

   2. With your shoes off, the pant legs should barely touch the floor. Leg length is very important - nothing looks goofier than pant legs that sit too high and your legs show above your sock. If you refuse to pay for the pants to be custom hemmed, err on the side of leg length being too long rather than too short.

3. Always wear a belt

   Pants have belt-loops for a reason. Use them. And no, wearing a belt is not an excuse to hang electronic gizmos off of it (see accessories.) If the belt matches your shoes (black or brown) so much the better. Minimal buckle size - avoid large intricate or cowboy buckles - keep it simple. One last thing: since you’re wearing a belt, you can put away those suspenders.

4. No funky colored or ripped jeans

   Keep ‘em blue or maybe dark black. No tie-died, no cheesy ripping, no stressed look. Definitely not tight and fitted, otherwise it looks like you’re wearing teenage girl jeans. The jeans are just background - they’ve got to be there, but your top will draw all the attention.

Standard “Can’t-Go-Wrong” Suggestions

Please note: the items listed below are girl-approved examples. Although each item is linked to a vendor that sells the item, we’re not advocating any exact make, model, or vendor. We highly recommend vendors which offer free in-store returns or free shipping on certain orders.

Jeans

Jeans are the staple of many a stylish guy’s wardrobe. With good reason - jeans can pretty much go with any shirt - except denim (unless you want to go with the Canadian Tuxedo). They are compatible with pretty much all footwear. Make sure you get a pair that is fitted all the way down. Try to avoid baggy jeans and also, don’t dismiss a pair of jeans because they have a button fly. Jeans should be extremely comfortable. I would avoid jeans where the denim doesn’t feel soft upon first touch.

Make sure they’re not too fitted/tight. Girls and skinny hipsters can pull that style off - leave it to them.

Khakis

For most white-collar jobs, the khaki will be your bread and butter. Again, avoid pleats and the dreaded taper. If you find a pair of khakis that fit you well, consider getting them in multiple colors. For example, a black khaki is a great choice for semi-formal events when you’d prefer a little more flexibility over a dress pant.

Dress Pants

Since you’ll be spending a fair amount of dough on these anyway, make sure you get them tailored for the actual dress shoes you’ll be wearing them with.