While browsing the Allen Edmonds website in search of a reasonably priced pair of brown suede loafers, I stumbled across these Randolph Verse Penny Loafers sitting quietly in the sale section. My first thought was, Well, that’s different. I’ve never owned a two-tone loafer, and the question immediately presented itself: am I stylish enough to pull these off, or am I about to become the cautionary tale at the next dinner party? Unsure of my own judgment, I did what any self-respecting gentleman in the age of artificial intelligence would do—I consulted AI and asked it to build a few outfits around them with clothes I already own. To my surprise, the silicon stylist delivered a compelling case. Before common sense had a chance to intervene, the order was placed. The shoes are now en route. Whether this turns out to be a masterstroke of sartorial courage or a valuable learning experience remains to be seen. Stay tuned.

What does everyone think of wearing hats on a regular basis? I recently went to a local hat store on a whim and decided to try on every type of hat they had, hoping to find one that didn't look awkward. Much to my surprise, I found one. A bowler/derby hat! Now its just a matter of getting comfortable wearing it out and about. What do you guys think? Is there a hat you wear regularly? Attach a pic!

I'll be turning 42 soon, and needing to maintain a professional appearance. I have curly hair (like coily curly), and in college, I started learning some care and styling tricks to allow some length for curls without simply a frizzy fro. I could use some help in two areas: (1) What are some professional hairstyles that are a little bit longer, to leverage the curls, but are also fitting for my age? (2) What are some care and styling tips for someone with really curly hair?

Is there a right or wrong way to wear a cowboy hat with a t-shirt? I don’t feel like wearing a long sleeve tomorrow it’s hot. The theme is cowboy. I was thinking my suede cowboy boots, jeans, tshirt and a cowboy hat.

I want to understand about men's bag as a fashion item. It is surely the most utility item a man can carry. But, often, due to lack of awareness, I just carry my back pack (which has very traditional looks). And I am beginning to realize that back packs are too old school and lack that oomph. Please help me here. What kind of a bag would you carry? If you already are into this, please post some pics and details.