A generally good overview, but you got a few things very wrong. “Step 3: Is it stylish?” I think you misunderstand the meaning of “stylish”. Style is an individual construct, not a quality that an object possesses. “Stylish” might be a man in his 70s wearing Jack Purcells with a seersucker suit, or a college student wearing his father’s old tweed sportcoat over a turtleneck. So your question is impossible to answer, because whether or not something is “stylish” will depend entirely upon the wearer’s individual style. You may have confused “stylish” with “fashionable”, and fashion is *not* for grown men. “5. Holey and unnaturally faded jeans are deal breakers.” No, JEANS are deal-breakers. Jeans were originally created for mucking out stables; i.e., cleaning horseshit out of where the horses shat. They were then adapted for gold-mining. You’re not doing either, so stop wearing jeans; you look like a teenager trying to look bad-ass. Jeans are also the most utterly impotent signifier of youth and rebellion in common use today. You might as well wear a sandwich-board that reads “please think I’m a tough rebel!” LAME. Grown men wear trousers, be they cotton twill, moleskin, flannel, tweed, whatever, but NOT indigo denim. “12. Pocket squares are meant to complement, not match.” I quibble, but a pocket square shouldn’t look like it was an origami project. The more studied and fussy and geometrically regular it looks, the more suspect the wearer looks. It should literally look like it was picked up as an afterthought and tossed into the pocket. The best way to achieve this effect is to pinch the square in the middle, pull that middle through your other hand’s fingers formed into a circle, and when you get to the point where equal lengths are sticking out of each side, fold the extended half over the 4 open points, and stuff into your pocket *without looking*. You can always check out the effect in the mirror afterwards and tweak it if needed, but it really must look uncontrived. “13. Cuff links can make or break an outfit.” So can a watch, and the watch depicted is an embarrassment. A watch is first for telling time, second, for your enjoyment and gratification and third, for impressing others. A watch is NEVER for shouting “I can time three different sprinters with 1/5th second accuracy while determining the phase of the moon!” Such watches are only worn by three kinds of men: technodweebs, the nouveau-riche, and coke dealers. Are you one of those three? Knock yourself out. A grown man wears a watch he’s inherited from his father (or better yet — his grandfather) or, if he isn’t so lucky, he buys the simplest and most discreet wind-up watch he can from a centuries-old company like Breguet or Vacheron-Constantin. (Yes, I realize that the watch pictured is a Breguet, but it’s neither discreet nor simple.) You get extra points if your watch was made before you were born. Extra-extra points if it’s white gold or platinum; minus-points if it’s yellow gold. Carry on, then.