While I do love a guy who can rock a suit or a tuxedo, I realize that it is simply not possible to dress up every single day. Sometimes it has to be jeans. That said, despite the fact that a pair of jeans is just about the most uncomplicated garment out there, it is amazing how many ways people (men and women) find to screw it up. Tapered jeans... Baggy jeans... Baggy tapered jeans (shudder)... Jeans worn with stinky sneakers... Too-tight jeans... The list goes on and on.
Folks, please, I beg you - take some time and find jeans that fit. Yes, that means actually going out there and trying them on, instead of grabbing three pairs in the size you think you are off the shelf and just hoping they will fit when you get home. They don't have to be designer. They don't have to be trendy. But they DO have to fit you. Going casual need not mean being sloppy. In fact, looking great is not at all a factor of the level of formality of your outfit - it's how you wear it and how it fits you.
Here is Gerry in one of his most laid-back incarnations. The jeans are Tommy Hilfigers - bought at an outlet for half the price - in a very basic denim wash and classic fit. Tommy sizes do run kind of weird, so Gerry had to try on several pairs - grabbing a range of waist and inseam sizes - until he found the one that was right.
The shirt is Champions but also from a discount store (I think it's from Ross but could be T. J. Maxx). It's light and comfortable, but a lot classier than a t-shirt, and besides - it's wrinkle-free. These come in a variety of colors, travel great and dry fast. So, if you are a casual dresser, consider getting several of these in the colors that suit you and retiring your college t-shirts for good.
The shoes and belt are light brown leather. The shoes also happen to be designer - Steve Madden - but also from a discount store. Don't scoff at those places, guys - you can seriously beef up your wardrobe for a fraction of the cost by shopping places like Ross and Marshall's as well as your local outlet malls. Back to the shoes - they are what the British call "trainers". I call them an awesome alternative to sneakers. They are just as comfortable, but don't scream, "I belong at the gym but my owner wears me EVERYWHERE else, because he is too lazy to invest in decent shoes!"
Because he is nearly always on the run, Gerry always wears a watch. However, he understands that the same watch is just not going to work across the board, so he has more than one: a formal one, a business one, and a casual one, like the one shown in the photo. It's still a cool watch, but it works with the outfit and looks like it belongs. The devil, indeed, can be in the details...
P.S. The cat is optional. :-)