Well, It's obviously not, "don't talk about monogramming." So we did just that with someone who inarguably knows her stuff. "After 100 years in business, we’ve learned a thing or two," says Rhett Croghan of Croghan's Jewel Box, a Charleston, South Carolina, institution. "The most important rule to keep in mind is that there are no rules anymore!" she explains. Phew! That said, there are a number of things to keep in mind when taking the initial leap, whether designing for yourself, as a gift, or to commemorate a special occasion. Read on for her breakdown.