There’s a few cycling items that you should never cheap-out on. The one thing that will enhance the enjoyment of riding more than anything else is a good set of cycling shorts.

There are a few premium brands out there. The ones that I particularly like are Assos. These shorts are unbelievable.Your jaw may drop when you first see the price but let the folks at Assos tell you a bit about them and you’ll immediately recognize their true value. It’s a thankless job being a good set of shorts. If you don’t notice the discomfort of sitting on your ass for hours on end, then they’re doing their job perfectly. I just did a 299km ride in my Assos shorts and I didn’t come out with one saddle soar or any of the usual discomforts.

I’d recommend that you first buy what fits, then determine their "value" taking into consideration the expected longevity of the shorts. An awesome pair of $250 shorts over five years has much more value than a crappy pair of $50 ones that lasts one year.

A few things to consider when buying a good set of shorts:

Bibs. Bib shorts can’t sag. They keep the chamois snug against the crotch to limit movement and irritation. They should feel a bit tight around the shoulders when standing straight up, but bend over into a riding position and they’ll loosen up.   I think that buying bib shorts goes without saying for any self-respecting cyclist.