Let's will explore the history and symbolism behind rings as well as the rules behind wearing multiple rings at the same time.
Men's Rings: Beyond the Wedding Band
Men's rings are making a comeback, but you may still not be sold on the idea of wearing anything on your fingers other than a wedding band. Aren't rings for girls? What finger do I wear them on? Can you wear more than one at a time?
Aren't ring for girls?
Rings are worn by both men and women. And in fact, men have worn rings for centuries, especially men in power. Even the pope wears rings. This is because rings can be worn not only to signify your marital status, but they can also represent professional affiliations (signet rings) or be precious family heirlooms. Men's rings are accepted in almost all parts of the world, although male designs tend to be more minimal and simpler than women's styles.
What finger(s) should I wear a ring on?
As with all fashion choices, the final decision is ultimately up to you, your personality, and the look you're trying to achieve. It is also dependent on what's socially accepted or recognized within your culture or geographic area.
The Ring Finger
Before advancements in medical science, it was thought that this finger contained a vein that linked directly to the heart, so of course, it made sense to wear your wedding ring on the finger with the closest tie to your heart full of love for your spouse. Science has instructed us differently now, but the tradition has stuck.
Wearing a ring on your wedding finger really didn't gain a lot of popularity until the mid-20th century. With men going off to war, rings were kept as mementos of their loved ones at home and were often changed to official engagement or wedding rings once the soldier returned.
Right or Left?
It depends on your culture. In American culture today, married men are expected to wear the wedding band on the ring finger of their left hand. It's often the first place a woman will look when attracted to a man to gauge his marital status. Men have been known to remove their wedding rings to deceptively attract other females, but you must always be careful of the tell-tale tan line where the ring once was.
In other parts of the world, for example, South America, Germany, men wear their wedding band on the right hand. In others, men wear the ring on their left hand while engaged and then move the ring to the right hand once married.
Pinkie finger (or Little Finger)
Symbolizes: Historically, the wedding band was worn on this finger, sometimes stacked with a signet ring. In American culture, pinky rings are oft associated with criminals and thugs (a la "The Godfather").
The most common rings men wear on their pinkies include rings representing professional or trade affiliations, or signet rings, which are often treasured family heirlooms.
Middle Finger (also known as Tall or Long Finger)
Symbolizes: responsibility and balance
Because of the commonly-associated obscene gesture, many men don't wear a ring on their middle finger. It also feels too obvious and often gets in the way. Because it is a less-common and bold choice, it is more noticeable and can even be a conversation starter.
Index Finger (a.k.a. Trigger or Pointer finger)
Symbolizes: power, authority, leadership
If you want your ring to get noticed, wear it on your index finger. Because this finger is often the biggest finger, you'll need a ring with substantial size to keep it looking proportional. Biggest downside is how frequently a ring on the index finger can get in the way of tasks.
Symbolizes: wealth and influence
Because the thumb is the most-used finger in general, it's easy to see how a thumb ring would easily get in the way by restricting movements and affecting your grip. This is precisely why the thumb ring symbolizes wealth -- those in the upper class didn't need to do any work where it would be in the way.
Nowadays, it is a bold fashion choice for men, and again, since the thumb is quite large, you'll need a solid piece of metal to maintain proportions.
Can I Wear Multiple Rings?
How many rings can I wear?
Frankly, it's up to you. You can wear one on every finger, even stacked, which gives off a very specific image. Generally, less is more, so 1-2 rings are ideal. If you already have a wedding band, an additional ring on the right hand provides balance without being too "blingy."
Do they have to match?
Rings generally match best with rings of the same metal -- gold with gold, silver with silver or platinum. But don't go exchanging your wedding band to match your favorite new ring just yet. Wearing different metals on opposite hands are a good way to avoid any clashing, and bonus points if the other ring matches your cufflinks.
Can I wear more than one ring on the same hand?
Yes of course. Although, having rings next to each other-- for example, a pinky ring and wedding band-- can result in uncomfortable scraping or pinching. Often times, men will stack their signet ring and wedding ring on top of one another on the same finger. However, note that too much stacking or too many rings on a single hand might make you appear more gypsy or pirate than well-accessorized.
So much like any fashion choice, the decision is yours alone. Some men may find that rings are more nuisance than nice, or maybe too impractical for their needs. Knowing yourself and what image you want to portray will help in deciding if rings, and how many of them, are right for you.