Ever since I was a little kid, I’ve been drawn to male-friendly accessories. These days, I’m like two bracelets and an ascot away from being on Johnny Depp’s level, which is the highest level.

But accessorizing can be tough. Here are a few guidelines I’ve picked up since I got my first Timex in first grade.

• Watches are probably the most prominent male accessory (excluding wedding rings), and the accessory that was most pragmatic until everyone became attached to their cell phones, thus making watches a non-necessity. However, wearing a watch is something that will never really go out of style, and it gives you the opportunity to pull out your phone less often than you already do, which is probably not a bad thing. Since watches are less useful than they used to be (and as such garner more attention), you may as well get a little bit weird with it if you’re going to wear one. I own a Casio calculator watch that functions very well as a conversation starter and as a quick way for me to flesh out what equals a 15 percent tip without using my phone or mental math. Also, if you dress casually, a Rolex is a good way to show people you’re monetarily successful (and/or don’t have children you need to spend a great deal of your income on). The contrast is intriguing when you see a person in jeans and a T-shirt wearing a Rolex.
• Don’t wear a pocket watch. There’s no way to not seem pretentious if you do.
• Baseball caps are fine in certain situations, like if you are wearing one that touts your favorite sports team while you are at a sporting event, or if you are a bald man who does not like people to know that you are bald. Otherwise, use baseball caps sparingly. A general rule is that you will look better without a hat than with one, unless you’re a man who can pull off a snow hat or a fedora. (Women are just better at pulling off hats. It’s the way it is.)
• I type this while wearing a thin brown leather bracelet on my right wrist, but you should be very careful with products made chiefly from leather. Keep away from thick leather cuff bracelets, and be wary of the gaudiness of your watch if it has a leather band. Otherwise people might mistake you as a woefully out-of-shape ultimate fighter.
• Avoid yellow gold rings unless you’re married, at which point you should wear that ring on your left-hand ring finger. Don’t wear a ring on your left-hand ring finger unless you are married. If you’re looking for a conversation starter that is not so gaudy, go with a subtle claddagh ring. As soon as a woman sees that you’re wearing one, she’ll want to see which way it’s facing, to know if you’re single or taken. I wear mine on my left index finger. Sometimes people confuse it as a wedding ring and I get to tell them I’m the furthest thing from married a person can be and by the way are they single?
• Don’t underestimate the power of symmetry when it comes to earrings. You don’t want to be wearing an earring in only one of your ears (unless it’s cartilage). Billy Idol could do that, but you can’t.
• If you’re questioning an accessory choice, it’s either a horrible idea you shouldn’t go with or a great idea. Best way to find out is to give it a shot and see how people react.
• If an accessory has personal meaning to you, you can pull it off no matter what. Accessories are like tattoos in this way, except more temporary. I’ve been wearing rubber bands on my right wrist since sixth grade (because they represent the struggle, man). I’ve worn the same rope anklet for three straight years because my mom gave it to me when she came to town for a visit. I have a rope bracelet with an anchor clasp because anchors have a personal meaning to me.