For some guys, it was fumbling through a sweaty, anxious prom night. Some late bloomers even wait until their wedding day. Whenever you had your first experience, you probably cherish the memory as a meaningful step towards becoming a man. We’re talking, of course, about the first time you put on a pair of cufflinks.

Cufflinks, more than any other accessory a man can wear, stand out even when you try to hide them. Like that rug in the Big Lebowski, a pair of cuff links can really tie your look together. So how do you find the links that match your style? ? In the words of ancient Greek philosopher Epictetus, “Check yourself before you wreck yourself.” Wait…that was Ice Cube. Epictetus said, “Know first who you are, and then adorn yourself accordingly.” Either way, the point is the same, start by looking at your personal brand. Are you The Boss Man, The Manager, The Creative or The Upstart?

You’re one of the new breed of entrepreneurs, young, ambitious, and cutting-edge, yet always mindful of the old-school fundamentals of success…like good old-fashioned hard work. Your style reflects your hard-charging attitude. When you walk into a room in a fine suit and place your briefcase on the desk, revealing an elegant pair of cufflinks everybody knows you’re running things.

Your Cufflink Collection
As the boss, you can wear a French cuff shirt and cufflinks whenever you damn well please. Our suggestion?  Have at least five pair of links and five French cuff shirts. That’ll get you through a work week without ever dipping below the high bar you set for yourself when you show up on Monday looking fly as hell.

How to Wear Them
The key word is refinement. Nothing says nouveau riche more than a pair of overly flashy cufflinks. Look for understated handcrafted links that reflect your “I got this” personality. Hefty metal cufflinks are just what the doctor ordered.

Shopping Tip
On your best links, both sides are designed. You don’t do anything half-ass, so don’t do anything half-wrist either. Vintage cufflinks, like the gold-toned hourglass link in the title image above, can round out your collection.

As a middle manager you are the conduit between the top brass and the less experienced young’uns. Perhaps you always deal with the tougher customers or you’re just damn good at juggling an ever shifting landscape of priorities. Your style echoes your personality, so when you rock the French cuffs and the cufflinks, it’s not about putting on airs, or “dressing up” but about showing a little spirit. It means you woke up in the morning and said, “let’s do this!” For you, wearing a pair of cufflinks says, “I’m not to be trifled with…” Wearing the right pair of cufflinks says, “…but I do enjoy a good joke.”

Your Cufflink Collection
Two or three pairs of cufflinks and French cuff shirts are sufficient. Wear them everyday and you begin to look like a social climber. Wear them only for special occasions and they begin to seem too precious. Instead, break these bad boys out a few times a month and they’ll give you a little lift that’ll rub off on everyone around you.

How to Wear Them?
The contrast in your French cuff shirt collection should match your intensity. While a stark white shirt is failsafe, a contrast collar and cuffs would be a bit much for Tuesday’s operations meeting. Try a blue or pink shirt to tone down the overall effect.

Shopping Tip
Look for color. With a neutral palette, a pair of cufflinks with a color that is in the same family as your pocket square or tie, or even socks can bring some boldness and vitality to an otherwise low intensity outfit.

You express yourself through writing or design or some other creative field. Your job is to capture lightning in a bottle, over and over again. But as glamorous as it may sound, being a creative is hard work and takes practice, just like anything else. You must constantly remind people that you don’t just sit around drawing pictures all day, so your style must reflect professionalism. Still, your personal brand means you should express your creativity in everything you do.

Your Cufflink Collection
If you never wore one French cuff shirt in your life, nobody would be surprised. All the more reason to own at least one. Truly creative people are full of surprises and breaking the mold with your style is no different. Your cufflinks are like sunny days, wear them often enough to be appreciated, but not so much that people start to take them for granted.  We’re looking at you California.

How to wear them
Want an easy way to appear unoriginal? Wear the same and French cuff shirt and cufflinks over and over again. To stay fresh try a service like Freshneck that lets you check out accessories the way Netflix does with DVDs.

Shopping Tip
Tone down the irony. Cuff links as satire is a once-in-a-while move, not a sartorial standard. Your cuff links can be fun but they should never look like you’re wearing them to make fun of guys who wear cufflinks.

You, young man, are on the rise. You’ve got big dreams and a tiny apartment. Maybe you’re interning at a place you want to work at or own someday. An intern in French cuffs? Hell yes! You’ve noticed how the big dogs around the office are peepin’ your style and you want to make your mark.

Your Cufflink Collection
It may seem counterintuitive but wearing cufflinks more often will make it seem like less of a special occasion when you put them on. Now is the time to pick up a few French cuff shirts. Try mixing French cuffs into your routine once or twice a month, especially in the summer. Three or four pair of silk knots and one pair of metal links for formal events will serve you well.

How to wear them
Appropriate is the key word for you. Your sense of style ought to impress the boss, not upstage him. Your cufflinks should reflect your youthful exuberance with pops of color. Try convertible cuffed shirts with barrel cuff buttons and buttonholes on both sides (think single layered French cuff) that also allow for cufflinks.

Shopping tip
Even on an intern budget you can manage to pick up silk knot links by the handful. With so many color combinations and two-toned versions you can probably even find your school colors. Suddenly your wrists are an intro to your resume…

Boss Man: “Nice cufflinks.”
You: “They’re my school colors.”
Boss Man: “Where’d you go?”

Game on.

One Last Rule

Now that you know the rules of the cufflink game for any type of gent, go ahead and throw ‘em out. Pick a pair of cufflinks you love, snag them and rock ‘em. The truly stylish gent knows that style rule number one is “dress for yourself first, even if you gotta break the rules sometimes.”

Got a favorite pair you’d like to tell us about?  Have a question for us?  Leave a comment below!