The Playboy’s Guide To Cufflinks

One of my favorite accessories when suiting up, is cufflinks. It adds that final touch and takes your style from solid to swag. Whether you’re a veteran or a newbie to rocking I Gemelli da Polso (French for cufflinks), I break down exactly how to wear them, what to wear them with and I even give you some extra style tips.

If you’ve been searching for a cufflinks guide, you can stop now, pour a drink and read the most comprehensive cufflink guide on the web: The Playboy’s Guide To Cufflinks.james-bond-cufflinks-1

How To Put On Cufflinks

Odds are you have regular cuff dress shirts which already have a button attached, but if you don’t, this chart also shows how to do it. Generally though, you’ll almost always be rocking cufflinks with a French cuff shirt. These are essentially double cuff shirts without an attached button and are designed to be worn with cufflinks. I personally am a huge fan of French cuff shirts, and almost always wear them.

Note: the side of the cufflink that has the design goes on the OUTER side of your cuff facing away from your body.



When To Wear Them: “Whenever you feel like it”

Like the cat mentioned in the video, I too wear different cufflinks based on my mood.

Some nights I’ll rock some like these:


And on another night where I feel like being more flashy and perhaps I’m celebrating an occasion, I’ll rock something like these:


The key is to not wear cufflinks that don’t reflect your personal style. If you’re not a flashy cat, then get a pair of classic conservative cufflinks. If you get a pair that you don’t like, then you’ll never wear them.

Remember too, that you don’t have to break the bank. One of my favorite pair of cufflinks I bought for less than $10 at a vintage store. They struck me as telling a story, so I bought them.

Different Styles Of Cufflinks

There’s a million different types of cufflinks, in a myriad of colors, shapes and sizes, but err on the side of classic when selecting a pair. Here’s a few pictures to give you an idea of what to select when you get your first pair.

Here’s a pair of new cheapass links that sell for only $3 on Amazon. Now don’t be surprised when they snap off after some wild night on the town, but this gives you an idea of how cheap they can be bought for.


I would suggest stepping it up and getting a mid-range pair ($55) like the ones below. The pearl and rose gold is a nice touch as well. Note: match your cufflinks with your watch. Don’t wear a silver watch with gold cufflinks. Gold with gold. Silver with silver. If you have a leather band watch, then match with the face. 


If you have cash to flash, then drop some more coin on these. Coming in at a cool $250 you can tell the quality pops more, as does the price tag.



What To Wear Them With

Suits and nothing but suits. You should obviously rock em with an outfit like this…

Monsieur Jerome

…and even this…

David Gandy M&S Summer 2014 (12)

…but never wear cufflinks without a suit coat. Never. You’ll look more like a waiter, than James Bond, I can promise you that.

Cufflinks are a great men’s accessory just like pocket squares, so have fun with it. Use common sense when matching colors and patterns. Match dressy links with dressy suits/outfits and more casual links with sport jackets and like the outfit above.

Style is in the details, so if you skimp on the details, you’re skimping on your swag.

If you’ve never worn a pair, drop $5 on some and try them out. I guarantee you’ll get hooked, just don’t be surprised if your one night stand success rate skyrockets.

Confused about fashion? Get the men’s guide to playboy style here.

Read More: How To Pick A Cologne

8 Replies to “The Playboy’s Guide To Cufflinks”

  1. I personal love the steampunk cufflinks. However, I been experienced for few times by buying those steampunk cufflinks with non-working watch movement.


  2. Absolutely no exceptions to cufflinks without a jacket? Don Draper does it all of the time. Obviously it’s just a TV show but it got me wondering if there was an exception to this.


  3. Great post. I started wearing cufflinks two years ago and find them to be very classy. They are a great conversation piece especially since no men seem to wear them anymore. There’s a few antique stores that sale them in my area that I’ve bought from. Some of the upscale jewelry stores sale 24K ones that go for about a grand or higher. Definitely a great way to stand out.


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