The first synthetic chamois was developed by Maurizio Castelli around 1980, says Steven Smith, brand manager for Castelli. Nearly every clothing manufacturer today uses synthetic materials—a mixture of open- and closed-cell foam and gel insets—that reduce both chafing and road noise.

Squishier doesn’t mean better.

Walk into any bike shop and you’ll see riders poking and prodding the chamois pads in various cycling shorts, looking for the softest, squishiest padding they can find. That’s a mistake.

“Pad density is the key,” Herlinger says. “Between eight and thirteen millimetres is an ideal thickness. Over time, pillowy padding is going to compress; it might not make it two months before it compresses down to almost nothing and is nearly unusable.” That’s because the more the padding compresses, the more pressure it places upon the exact area you’re trying to keep pressure-free.

While you’re at it, Herlinger suggests buying a breathable, anti-microbial chamois that will eliminate moisture and friction, the two biggest chafing culprits. You should also pay attention to the seams attaching the chamois to the shorts. Look for flatlock stitching that lays flat.

“You don’t want a raw edge (of the stitching) down below,” Herlinger says, unless you’d like to rip up some skin.

You can borrow women’s cycling shorts if you’re a man, and vice versa.

With advances in moulding techniques, companies are able to mold chamois to more anatomically correct shapes. Both a male and female chamois typically will resemble an elephant’s head, with the female chamois having wider ears to accommodate women’s larger hipbones, and a shorter, rounder nose. Many cycling shorts use multiple densities and thicknesses of chaomis padding specifically chosen for the unique demands of different anatomical locations, says Simon Fisher, cycling apparel store Giro apparel’s product manager.

“The contours between a saddle and the human body are incredibly complex and it’s impossible for a completely flat chamois to properly follow those curves,” Smith says. Noticeably, many chamois place higher-density foam underneath your sit bones, and thinner foam situated against more sensitive areas.

While there are significant differences between chamois, Smith says, men can still wear women’s shorts and vice versa, if need be. It definitely beats the commando-riding alternative.

You can tailor chamois padding to your riding style.

Club Ride offers chamois of different thickness and contours based on the number of hours you expect to ride, while protective bike gear developers POC Sports makes different chamois based on the type of riding you do.

“POC has six different chamois, and each is built to optimise comfort for different types of riders and riding,” says POC representative Patrick King. “POC’s Chrono chamois, built for TT racing, uses longer inserts of silicone padding to support an aero position, while the Fondo chamois has more silicone padding on towards the back of the chamois to support a more comfortable, upright riding position for longer, mellower rides.”

How much does the shape and contour of the chamois matter? A great deal, which Herlinger found out the hard way when he put his shorts on backwards by accident.

“It was early in the morning, and I was getting changed in the back of a dark van,” Herlinger says. “We’d just started our five-hour ride, and I knew right away that something was wrong. I finally figured out what I’d done and corrected matters, but it was a bit too late. There was a lot of rubbing happening in all the wrong places.”

Wash those shorts!

No one likes to do laundry, but you should rarely, if ever, wear a pair of shorts twice without washing them first.

“That’s a prime place for bacteria to grow, and with a bit of abrasion on the skin from riding, it’s an easy place to start an infection,” Smith says.

Although many shorts have some anti-microbial properties built into the chamois that might protect you when riding in the same shorts multiple days in a row, those properties eventually fade away after repeated washings.

Nothing lasts forever, not even your chamois.

So what’s the typical lifespan of a chamois? It really depends on the rider—how much saddle time they’re putting in, their weight—and the type of short they’re wearing.

“The best indication it’s time to replace your chamois is discomfort. Over time, chamois padding will eventually become ‘packed down’ and become unable to perform its function,” says Fisher. “But eventually even the best chamois won’t have that same supple comfort it once had. Basically, a good chamois should ‘disappear’ during your ride. If you’re actively noticing your chamois, it’s time for a new one.”