There has always been something charming about things in my life that get better, more comfortable, more familiar with each use. I find that the same charm applies to clothing.
Sure, the excitement of a new shirt, or pair of jeans is a wonderful thing. But it doesn't relpace the feeling of slipping on that pair of jeans that have fit perfectly for years, and instantly make you feel like a million.
Designers are drawing on the nostalgic feeling that we all crave and recreating classics, and even wearing them in for us. I'm not talking the "Abercrombie" worn in, but a more graceful approach that doesn't make you look like a tween.
Most recently we have seen a resurgence of the chambray shirt playing into the whole Blue Collar trend.
Its not the easiest thing to wear, especially when paired with jeans,
the whole blue on blue can get a little confusing.

For ease, look for a lightweight chambray and pair with cuffed khakis-
or even a pair of linen pants.

Try pairing a chambray shirt, under your gray suit for a more 9-5 friendly look.