I recently lost alot of weight and am in the process of getting a new wardrobe, and I am trying to get a bit more stylish. I am an attorney, 34 years old, but work for a County, meaning our office is relatively casual, and I do not get to court that much. I typically wear a shirt/tie/slacks to work, no suit. Nobody at the office really dresses more formal. I got a whole bunch of dress shirts and slacks which FINALLY seem to fit me well. (15 neck, trim fit, 34"w, 42" jacket size). The shirts I got are not sports shirts, but are the regular dress shirts, but I decided to go a little more stylish and get some stripes and checkered shirts. I found plenty on sale at Lands End for about $18-25 a pop, so I figured I can't go wrong with those. The solid shirts have the non-button collars. Later on, I will branch off into the fancier shirts, but I want to establish servicable clothes first that don't cost me a fortune. For $18-25, I can't go wrong with Lands End shirts, right?? This might be a dumb question, but I am curious whether there is anything wrong with wearing a dress shirt (not sports shorts) with the buttons on the collars? All the high end shirts I saw at Nordstroms had the non-buttoned collar. Am I committing a major blunder here? I have some shirts without the collar buttons. Also, I am trying to go a bit bold with stripes and even some checkered patterns. While I am not doing anything insane I think, they are a bit more loud than the more muted shirts I saw at say Nordstroms. Given my age and work culture, am I OK with going a bit bolder? I am careful not to have the tie clash with the shirt. Before, all I really wore were solid shirts and boring ties and boring slacks, which certainly didnt clash and looked fine and professional, but of course were boring. I want to venture into some checkered pants...not madras, but ones a pattern and even checkered pattern. It does not appear "loud". I am sure I can wear a solid shirt with the checkered slacks, but what about a striped or checkered shirt with those pants? Also, to confirm: if I am going to court or wear a suit, should I only wear the non-button collared shirts? I am assuming for something like that, I should stay away from a checkered shirt in general, right? Last question---I am wearing $18-25 shirts, $50 100% wool slacks (everything I buy is clearance and I think is at least serviceable quality) but I have a thing for ties, and have some $50 ties and want to get a $100 tie. Is something wrong with having a tie that costs more than a shirt and pants? Is this, for a lack of a better word, dumb? Actually, I have a final question about shoes...I don't like penny loafers, but I have two laced dress shoes, black and brown. What else can I do other than having black and brown? Are there any real options here?