I love cufflinks; all but one of my dress shirts have french cuffs. As a matter of fact, unless I absolutely love the rest of the shirt, and I’m buying it at a discount, french cuffs are a prerequisite. I covered the different types of cuffs in my Guide to Collars and Cuffs, but as a quick refresher, this is a regular button cuff:
And this is the french cuff:
When in doubt stick with the basics.
My favorite cufflinks are a pair of plain silver-coloured ones that I bought on eBay years ago for about $7; I wear them most days, they are simple, elegant, formal, and match with my other accessories.
For more formal occasions I have a pair of black and gold cufflinks (similar to the pair pictured) that I picked up for $10 at a thrift store.
What they have in common is that they are both subtle, and simple designs; things that don’t stand out or draw attention, but will still work with most outfits or occasions.
A bit of subtle flair
The basics are good, but cufflinks are a perfect way to add a bit of flair to an outfit, without being over the top. I’m fond of adding a bit of colour with glossy enamel cufflinks; I like a Fleur-De-Lis motif, but you can also show off your patriotism with flags, or your school pride (assuming you went to a school fancy enough to have its own cufflinks). Old coins can also be turned into unique cufflinks.
A Little Novelty
Novelty cufflinks are a great way to subtly show off your interests, and can work as good conversational pieces (just don’t be the one to draw attention to them). I have three sets of novelty cufflinks; a pair of playing cards, dominoes, and a pair that are actually 8GB flash drives (so that I can pretend to be a spy).
These types of cufflinks are fine for everyday office attire and more casual events, but I wouldn’t bring them out for formal occasions or first dates (the second or third date should be fine). If you do have a formal occasion, your best option is…
Black and White (and Gold)
When it comes to black tie events, your best option is either Mother of Pearl, or black Onyx; the setting should either be Silver or Gold. I prefer Silver with Mother of Pearl, and Gold with Onyx.
Notice the cufflinks in the image above are double-sided, and joined by a short chain; these are considered the most formal type, and are the best option for Black Tie.
When To Wear Them
French cuff shirts are generally perceived as more formal, but the truth is they are acceptable in every situation that regular button cuffs are; the degree of formality would be determined by what else you are wearing (suit, sportcoat, blazer, etc), and the cufflinks that you choose. Ultimately, wear them when you have the desire.
If you are looking for a more in-depth guide to cufflinks, check out this article by Real Men Real Style; it goes into great detail about the different types and styles of cufflinks, and I recommend reading it. It also has lots of pictures.