It's very easy to pop on that solid tie and solid shirt and solid suit... I know the President does it every day, but you aren't that guy shackled to a desk and followed to the bathroom by two men in sunglasses, so you can dress a little more boldly like they did when Fred Astaire and James Stewart were gracing the big screen.
When putting similar patterns together, ensure the patterns are of different scale.
Big stripes - small stripes
Big dots - small dots
Big windowpane - small windowpane
Ray Milland wearing a fine striped shirt with a broad striped tie. The bolder tie takes the attention and the similar patterns in different scales don't fight.
It's not always advisable to mix three stripe patterns, unless you have one that is subtle and very much part of the background (the shirt) and two that are bolder. The two remaining stripe patterns must be of different scales or the look will be very distracting.
When putting different patterns together, ensure the patterns are of similar scale.
Big stripes - big dots
Small plaid - small stripes
Big paisley - big stripes (or wide enough to balance with the paisley)
The scale of the pattern on the tie is in scale with the double stripe pattern on the jacket. Different patterns, same scale (I was on assignment that day, hence the press pass).
The broad stripes of the tie match the scale of the plaid on the jacket in the above outfit. Ideally, I'd have paired cream flannel trousers with the heavier jacket, but I thought the linens worked fine for this warmer day in L.A. The white cotton hanky shows I'm ready for anything.
If you're trying to match plaids with plaids... don't try to match plaids (unless you are really confident the outcome looks grand).
In this case, the little stripes in the shirt flow with the small lines in the broad plaid.
I like how focus goes to the bolder pattern on the jacket.
Outside of pattern matching, here are a few things you should keep in mind when putting it all together.
Socks don't need to match your pants. If you want to make a statement and wear something flashy that's fine; however, if you don't want your socks to own your outfit, your socks should echo the color of your pants. Don't wear black sock or white socks unless you are wearing black pants or white pants.
I have seen on several occasions where men have attempted to pair a solid color sport coat with a pair of trousers that is near to the color of the jacket, in effect, trying to create a pseudo suit... DON'T DO THAT. A suit is always a matching material jacket, vest, and trousers, and you can leave the vest behind at times. When you wear a solid sport coat, always wear trousers that are complementary to the jacket's color, far enough away from the jacket's color so as to not be confused with being a suit.
Light beige jacket with brown trousers.
Oatmeal colored jacket with british khaki colored trousers.
Light brown sport coat with dark brown trousers (ignore the ankle skin, it was a bad sock day for me).
Follow these basic rules and over time you won't end up blinding your friends with pattern confusion when you run out of clean white shirts and are forced to pair that windowpane with those polka dots.
We'll discuss colors and hues at greater length in a later post... they are much more important to get right yet much more confusing to explain. Until then, a brief teaser.
A classic Hollywood jacket paired with a subtle arctic blue striped shirt, fine striped silver and red bow tie, the color not too red as to steal the show, and a Fair Isle sweater with a pattern bold enough to take the attention but coordinating in color enough to not ruin the show.