While not exactly divided, our house is in a quandary over shoes for my husband, I found these Calvin Klein black shoes for $45 at TJ Max that I was instantly drawn to for John. He says that they are not too uncomfortable for dress shoes (probably the best I'll ever get from him on any shoe in this category) and he isn't strongly opposed or drawn to them and prefers to just trust my judgement. The problem is, I don't fully trust my judgement when it comes to men's fashion. Enter almost 14 year old Ethan onto the scene. He is extremely opinionated about his own style (our pocketbook is $60 lighter due to his most recent shoe purchase - white converse). Ethan is not happy about the slightly squared off toe (even though over all it reads more pointy than square) and he feels like they look like a cowboy boot style, and "Dad is SO not a cowboy!" The new shoes are in photos one and two. Other than work boots for work, and a vaireity of sneakers for causal/play, John wears dressier shoes very infrequently. It's possible that if we keep these shoes, they will outlive him. Because of this, he has two pair of shoes that I'm sure are not very stylish anymore, although I felt good about them back when we bought them.. Once or twice every year when he needs to dress up for a wedding, funeral, or dressy party, John looks as these two pairs of shoes (photos 3 and 4) and bemoans his lack of appropriate shoes. The new shoes would nicely fill that hole, but none of us are confident enough about the purchase to decide. The last photo is of the one shoe that John wears to every single semi-dressy outing (church, date night, etc). He loves those shoes so much! I've just included these for reference on what he likes and what he has in his shoe collection. So... over to all of you, what do you think? John was quite happy with the idea of letting you stylish ladies (and men, if any want to weigh in) help us know wat to do. The clothing he would wear them with are black dress pants and button down shirts (sometimes with a tie) - maybe a jacket, but unlikely, and dark jeans with button down shirt and sometimes a jacket. I am also curious about the proportion of the long narrow shoe with his body type being thin and angular (he is 5'10" and very thin). I've included an old photo of John in what he typically wears to church and going out (what he wears with his favorite "driving" shoes, not what he would wear with these new ones). Thank you in advance for all opinions and advice!