Thank you all for the great tips and suggestions! I don't have a lot of button downs or pullovers but the ones I do could get more wear if I could feel more comfortable doing this. I've also found that I like layering patterned shirts to let only a little of it show. And at work it is usually either too hot or too cold so it's nice to have the option of removing or adding layers and feeling like my outfit still looks nice. I think pic #1 was my first ever semi tuck! And I would usually pair with black shoes and belt but upon being inspired by some of your pics went with the cognac/brown and like it so much better and it's opening to way more options! It's also the first time I didn't wear the purple pants with any other purple. I've always felt like I had to match it. So this was nice.
Tr3kkie9rl - actually the shirt in #2 and 3 are both the same sleeveless top. Probably only the second and third time I've worn it and I've had it a few years. I can see it's gonna get worn alot more now!
KKards - what is a BR?
Joy - I'll try that flannel shirt idea. How did you work your collar when you layered with the turtleneck?
Carter - Yes! Exactly! That's what I would always feel like! : )
Lisa - Yes it's "library". I work at an architectural firm and that's our Resource Library.