BBB, Gosh, I like these type of questions, but its just so hard to make a blanket statement of what every guy needs. If you're talking about the specific shoes pictured, then only you can make a final determination...you know what your own budget is, how they fit in with the clothes already in your closet, what your work environment is like, etc. But I got from the tone of your question that you would like opinions on the style or content that should fill out the initial, basic shoe wardrobe of someone starting from scratch. I think you have established a good starting point for the average guy. I would get dressy black lace-ups to start...cap-toe for myself, but a plain toe, Norwegian, or even wing-tip might work best for others....and make them the best that you could afford. You have got to have that one pair that you can start with that are rock-solid-last you more than a decade-no doubt about it-I am dressing up-shoes. From there, if you wear suits to work, the next purcase should probably be a brown or cordovan lace-up that are also seriously dressy. If work is casual, then a nice loafer might be in order. But you would want something substantial to rotate with your black pair. As an aside, when it comes to dress shoes, you are either a slip-on guy or you're not. I'm not much of a slip-on guy. I have one pair of tassel shoes that I would ever consider wearing with a suit, for instance, and I usually only wear them with sportcoats. I'm more of a lace-up guy when it comes to wearing suits. After that, personality really has to take over. Casual shoes are really directed towards whatever the casual activity is, if I may state the obvious. If you go clubbing a lot, then you'd probably go with a funky slip on, or Chelseas, perhaps sneakers if you are more the active type. The rugged among us may select something like the lug soles you pictured, or a boot, maybe chukkas. I do think its a good idea for most everybody to have something of an all-weather shoe, whether Paraboot, Timberland, Rockport, etc. with comfort and durability being paramount. I think that particluar pair of Ferragamos will look dated before too long, but the horse-bit style in general is probably a good casual shoe for most guys. I've been looking for the right pair myself for a while now. Possibilities become endless, but suffice it to say the prepsters will gravitate towards penny loafers. Athletic types will want more trainers. Bad thing about it is, you really can get hooked on buying shoes, especially the high-end types that the clothesies around here tend to favor.