So I've dabbled in cakes but have my 1st request for a cupcake tree. This is for a 60th birthday (female) & they would like each cupcake to mark a year (i.e. 1951, 1952). I originally thought something like a "baby" one the first year & then something for each following but they would prefer something more "elegant" -they suggested maybe a small flag with each year on it stuck in the cupcake? I don't know how elegant that would look. Any thoughts/ideas?

How about a little of both? You could make a banner for each cupcake/year, written in elegant calligraphy surrounded by some small flowers. Then, add a small embellishment on the milestone years, such as a baby on the first year, a diploma on the HS and college grad years, a pair of rings on the wedding year, etc.

a nice swirl with the number(s) on alittle plaque on top... like bumpy circle, circle, number... sorry the only way i could think to explain it! No flags..... lol

What type of icing are you planning on?

I think piping in dark chocolate on soft looking (not fondant) icing looks quite elegant (piped on greaseproof paper or similar using a nice script and transfered to the icing when set). Using silver metallic wrappers (or the lacy looking covers) with a few silver dragees could make them look quite elegant.

It would probably be possible to make the flags look elegant but quite difficult with a lot of scope for them to just look cheap, I would think.