This picture has been sitting in my queue for months. From both a casual and a detailed observation it’s pretty easy to see that this guy nails every aspect of dressing well. Dark, slim jeans that appear to have a natural fade, brown desert boots, perfect fit in the cardigan, the tones and colors are all great with each other and his complexion, top two buttons are undone, his hair cut is clean and frames his face well, etc.
But still this picture bothers me. This man looks to be the epitome of a cubicle jockey, the beta male who takes orders from everyone else and has a hard time building any real attraction from women. That may not be the case, but that’s the impression his overall appearance gives.
If he had even the slightest affected detail – like a gold pinky ring or a more aggressive haircut he would have a more masculine presence. Instead, he looks like the everyman.
The thing about all these style rules I talk about is that you need to learn them to learn how to properly break them. You don’t want to be so put together that you end up looking too safe.
Look at this picture. His shoes don’t match his belt, his jeans are extremely light, the small blade of the tie is twisted in the knot so it sits parallel with the large blade instead of behind it, the shoulder pads are way too big. All of these are broken rules, but since he does well with everything else, he can get away with it. It helps that he’s young so he can break more than one rule at a time, but even older guys can follow this advice : don’t look too neat or too clean.