Can you wear a fedora with cowboy boots? (Explained)

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Can you wear a fedora with cowboy boots?

The short and most direct answer to the question of whether someone can or can not wear a fedora with cowboy boots is simply put, yes.

There is nothing about the act or decision of wearing a fedora on your head and cowboy boots on your feet that necessarily defies the laws of physics or is otherwise regarded as unfeasible within the scientific community.

It is completely within the realm of realistic possibilities as well as human abilities.

Should you wear a fedora with cowboy boots?

In the case of whether someone should stylistically entertain the idea of combining a fedora and cowboy boots in the same outfit, it all depends on intention.

While the short answer to this question may be no, that sounds insane and is deeply conflicting in terms of intention, let’s indulge ourselves if only for a moment in time, into the circumstances that would permit such a style choice.

Let’s say you are at the airport, on your way to a sunny Cancun vacation, you have on your fedora and sunglasses and are ready for a good time in the sun.

Unfortunately, at the airport check-in, it appears you have overpacked your suitcase by roughly three pounds.

Instead of shelling out between $100-$200 for the outrageous overweight baggage fee, you for a second entertain the idea of kicking off those beach-ready flip flops, or super comfortable airport slides, and instead, throw on your ready to party cowboy boots. If this is the case, then sure.

Wearing the combination of a fedora and cowboy boots is not only a fine money-saving device, but certainly, a conversation starter and story rolled into one.

Let’s say it’s Halloween, and you are going for one of those conceptual costume ideas such as “a walking contradiction” or “under compensating for something” or going for comedic relief to break the ice, like “the washing machine shrunk my ten-gallon hat and left me with a fedora” then yes, this will surely garner at least a few chuckles and put you in the good graces of those light-hearted spirits at the party.

The important thing, however, is to keep in mind that you have now committed to the character of the absurd, never forget your gimmick, and you are going to look very strange to a lot of people you have not had the chance to meet.

This can be great because, now to not appear crazy, you must meet as many people as possible.

The trick here, however, is now you must stay in the absurdity of this character you have created for the entirety of the night.

Other than the two scenarios outlined above, men who want to be taken seriously by their peers should not wear fedoras with cowboy boots.

Do cowboys wear fedoras?

Not unless they are also undercover cops, infiltrating deep within the hive of outlaw drug traffickers in South Beach Miami, Florida, playing cards and smoking Cuban cigars while awaiting shipments to arrive at the fishing port.

But even then, it’s risky, because the combination of fedora and farmer’s tan alone would surely come across as wildly suspicious to the rest of the crew.

Or, perhaps, let’s say they are on vacation with their families on the outer banks, down along the palm trees lining the eastern coast of the Carolinas, and their wife got it for them as a part of some sort of surprise present package week-long get away from the farm, and now they are stuck wearing it just out of pure love of their wife and family and pure avoidance of conflict and unadulterated fear of altercation during an otherwise relaxing time.

What should men not wear with cowboy boots?

Anything outside the realm of jeans and flannel should be avoided when wearing cowboy boots, but it’s all up to preference after the point of commitment to something such as wearing cowboy boots while not doing cowboy activities or actively working on a farm.

Anything that has not been seen in a country-western music video, movie, at a rodeo, or is local to the midwestern to the southern United States, should typically be avoided in combination with cowboy boots.

This includes things like bathing suits, shorts, athletic attire, comfort wear such as sweatpants and sweatshirts.

What do you wear a fedora with?

One of the most important things to wear with a fedora is an attitude.

You must commit to the fact you have something between a children’s cowboy hat and a visor sitting atop your head.

This unique combination requires a fun personality who is down for anything.

You must be ready to adopt this attitude and hold on to it tightly for the duration of the time the fedora is atop your head.

Some things that are frequently put in combination with a fedora are Hawaiian shirts, shorts, sunglasses, flip flops, swimming trunks, and the occasional suit if you are going salsa dancing.

The most important thing is to make sure your clothing is light and airy to let in all the fun you are about to be having.

Final Thoughts

Ultimately, the decision to wear a fedora with cowboy boots comes down to intention, personality, and attitude.

However, for most of the population, this stylistic choice and combination should mostly be avoided.