From time to time, I cut-and-paste real questions entered into search engines that drive visitors to my website. I thought for this post, I would post the answer before the question. Read on (and pardon my bad attempt at humor.)

ANSWER: ON YOUR FEET.

Questions:
How are guys supposed to wear cowboy boots?
How do guys wear cowboy boots?
How do men wear cowboy boots?
How should guys wear boots?
How should men wear cowboy boots?
How to properly wear cowboy boots?
How to wear western boots?
How to wear cow boy boots men
How to wear cowboy boots & not look stupid
What is the proper way to wear cowboy boots?

… I am not making this up — I get about 200-300 visitors to my website every day from questions just like this. The above list were questions entered within a one-hour period.

ANSWER: YES

Questions:
Can a man wear brown boots and black jeans?
Can cowboy boot be worn over pants leg by men?
Can men wear cowboy boots with slacks?
Can men wear straight leg jeans with boots?
Can you wear cowboy boots with a tux?
Can you wear harness boots with a suit?
Should guys wear cowboy boots to work?
Should you wear cowboy boots while doing business in Texas?
Should I wear western boots for guys?
Should men wear cowboy boots?

More info here.

ANSWER: DON’T CUT JEANS. BAD ADVICE.

Questions:
How to cut jeans to fit over cowboy boots
How to cut your jean for boots
How to cut your jeans for cowboy boots

Seriously, if the ends of your jeans are to narrow to fit over boots, get regular straight-leg or boot cut jeans. DON’T cut your jeans. They will fray and be ruined in a few washings (that is, provided you wash your jeans.)

ANSWER: ALWAYS WEAR BOOTS

Questions:
When is a man too old for cowboy boots?
When should men wear boots?

A man is never too old to wear boots. Older, confident men learned long ago not to worry about what other people think.

ANSWER: CLOTHES

Questions:
What to wear with cowboy boots for work?
What to wear with black cowboy boots for men?
What can I wear with brown cowboy boots?
What looks good with cowboy boots men?
What looks good with cowboy boots on men?
What to wear black cowboy boots with men?
What to wear cowboy boots with men?

These questions indicate ongoing self-imposed concern and confusion about wearing boots. Get over it — don’t make it harder than it has to be. Wear boots. No one really cares or notices if your boots are a different color from your pants, belt, or shirt. Who really cares? No.big.deal. Be a guy — wear boots.

ANSWER: IN JEANS, IN A SUIT, IN BUSINESS CASUAL CLOTHES… WHATEVER YOU LIKE

Questions:
How to dress with cowboy boots for men
How to dress with cowboy boots men

I may also have answered a bit more tartly, but you get the point. Dress in clothes that help you feel confidence, then express it in how you walk, behave, smile, and interact with others.

Life is short: wear boots and don’t sweat the small stuff.