My job does not require me to wear a tie, but I often opt to wear one simply out of preference and my love of Kent Wang's grenadines and knits. I order all my shirts through Proper Cloth, and I'm planning on trying the Roma cutaway collar for my next order due to advice I've received on this site regarding its versatility with or without a tie.
Kentucky is a true four-season state. Our summers are in the 90s and our winters' snow. Most likely, I'll eventually need a handful of seasonal shirts in my rotation, but currently my closest is lean enough I haven't set that as a priority.
I almost always wear jackets and trousers as opposed to a suit. I've been considering introducing a fully suited look into my weekly rotation, but I'm already the only person besides my boss who wears a jacket or tie to work.
My main concern with shirts is patterns, colors, and versatility. I'm not sure where to start regarding stripes, checks, ginghams (I'm sure a few people just shuddered), etc.
Thanks for inquiring/reading!
The reason I asked about the tie and the jacket is that your answers will give us some indication of how formal your usual dress is (the reasons for the climate question is obvious, I assume), and that matters when discussing patterns.
As I’m sure you already know, other factors being equal any pattern is less formal than a solid. How much less formal depends on how vivid the pattern is, among other things. I wear a suit and tie almost all the time and when it comes to patterns I find widely spaced pinstripes against white to be the most consistent with that level of formality. If I owned any checked shirts I’d probably reserve them for odd jackets, although in my experience many bolder checks are best left tieless altogether.
For someone who does bolder stripes consistently well in what would be in many places business-appropriate fits, @EliodA comes to mind.
Edit: Here's an example of what I mean by "widely spaced pinstripes against white." The shirt is from Luxire.
Edited by Academic2 - 8/26/15 at 1:52pm