General Rule of thumb with ties: Big with small, small with big and medium with medium. Let’s explain: If you have a very graphic tie with a large pattern/design, you need to pair that with a small-patterned shirt (or even a solid color). If you have a very graphic shirt, you need to pair that with a solid or subtly-patterned tie. And, if you have a medium-sized pattern for shirt and tie, they will match perfectly.
Since the tie is the easiest way to show character and personality in dress, don’t be afraid of bold colors or graphic prints.
Socks of dark colors should be preferably worn because whites look too stark.
Pinstriped, dark-colored pants will make you look taller and thinner. To flaunt a broader upper body team them with a light colored shirt.
When buying straight-leg pants, buy them a size larger than usual so they hang on your hips.
Don’t ever wear head-to-toe labels.
When pairing pinstripes – pinstripe suits can be paired with pinstripe shirts, you just have to pair a different stripe (black and white pinstripe suit matched with blue and white pinstripe shirt).
When buying a button-down shirt, you can tell if it’s the right length by measuring it against your suit sleeve. The shirt cuff should protrude about 3 quarters of an inch from the jacket sleeve.
Rules for undershirts – Never wear a tank top under a linen shirt – it’s too obvious. Never wear a crew neck undershirt with a button down if you plan on unbuttoning it at all – in that case, wear a v-neck undershirt. Never wear a dark undershirt or shirt with lettering with a light-colored shirt – it will show through.
Sandals — only Hercules could get away with this. Flip flops are acceptable for summer.
Only wear shorts if your legs are tanned – and please throw away the “jorts” (aka, jean shorts)
According to fashion stylist Robert Verdi, only Ralph Lauren models can get away with black belts and black loafers in the summer. Get yourself a pair of saddle shoes or white bucks.
Ties should go with but not be of the same fabric of a pocket square/handkerchief.