Don't feel like you have to if you're not comfortable. Work your way up, getting used to dressing better is a process for most of us. The biggest part to pulling it off is confidence. If you don't feel natural with what you're wearing, then you're gonna come off as uncomfortable. Small steps is best. You came here, so you're clearly ready to take a step from where you are. After taking this step, you'll become comfortable taking the next one at some point, and you can make the jump then. But those wingtips are in a more casual leather, and as such are intended for more casual use. I wouldn't wear the natural ones with a suit. But with chinos? Hell yeah. On the loafers note, penny loafers are my go to, and I'm younger than you. Don't worry about the old man bit. Shockingly, things that come off as old mannish when worn by an older man take on an entirely different context when worn by a young one. I tend to recommend Bass. For the price, it's pretty hard to find a better shoe. http://www.zappos.com/bass-logan-tan-leather http://www.zappos.com/bass-gorham-dark-brown http://www.zappos.com/product/7505634/color/216 Give burgundy consideration for color as well. In regards to what shade of brown goes with mid and light grays; pretty much all of them.