“I care not what others think of what I do, but I care very much about what I think of what I do! That is character!” – Theodore Roosevelt

In the last few years, particularly with the hipster crowd, there has been a resurgence in manly dress and overall appearance: flannel shirts, beards, suspenders, sturdy boots, vintage clothes (or at least vintage looking) and antique accessories. What’s more, is we find it doesn’t stop with clothes but moves on to vehicles, the restoration of old axes -- which have the look of wear and use though that wear and use is not usually attributed to the current owner --, hand drawn and hand painted signage, slow brewed coffee, and of course local everything. There are a number of detractors of the cultural shift who would say this is just a materialistic trend which does nothing more than show the vanity of the generation. There may be some truth there, but aren’t we often vain about the things we pride? If so, I think we are taking pride in a number of right things. But I also believe that dressing the part, or playing the part, often comes before the real thing, and, I believe Theodore Roosevelt may be the best example of this in recent history.

The Dakota Dude

Dakota Dude

A Young Theodore Roosevelt all duded-up for his frontier excursion!

Before Roosevelt was the “Badlands Cowboy” or the leader of the Rough Riders, he was a spoiled, rich kid at Harvard. Though he had suffered physically as a boy, he knew luxury and privilege like few in his day. While he spent a good deal of time with the upper-class, his true draw was to the rough and tumble life of the frontiersman. 

An avid lover of the out-of-doors and budding hunter, Roosevelt pounced at the opportunity to head to the South Dakota Territory to kill a buffalo “while there were still buffalo left to shoot.” His heroes being Daniel Boone and Davy Crockett, he paid a small fortune to get gussied up for the trip: a deerskin hunting suit, a custom engraved Tiffany’s knife, ornate rifle, silver spurs also engraved with his initials, and a broad sombrero (not pictured). It did not take long for the hardened men of the Badlands to give him nicknames such as “the Eastern dandy” or simply, “that damned dude” -- a dude being the name for a man ornately dressed. However, in true Rooseveltean style, he proved himself to be worthy of the garments of his boyhood heroes. By the time he had returned from his excursion he had won the respect of the Dakotans and bore a physical change that matched the character of the man he had suited up to become. As one newspaper reporter writes upon his return to New York:

“[Roosevelt] was rugged, bronzed, and in the prime of health. There was very little of the whilom dude in his rough and easy costume, with a large handkerchief tied loosely about his neck…The slow, and exasperating drawl and the unique accent that the New Yorker feels he must use when visiting a less blessed portion of civilization had disappeared, and in their place is a nervous, energetic manner of talking with the flat accent of the West.” – The Rise of Theodore Roosevelt, Edmund Morris

The Badlands Cowboy

Badlands Cowboy

Roosevelt (centered) with two friends who managed his Elkhorn Ranch, years after his initial visit to the Badlands.


Roosevelt fell in love with the West, and over the years made many return trips, eventually beginning a cattle ranch (Elkhorn) in the territory. The ranch was more of an excuse for return hunting trips than a financial investment. Roosevelt had become one with the territory, but his penchant for ‘dressing the part’ was never lost. He always saw that rough wilderness as a place of adventure, and over the many years, adventures were had! From punching out a rude, drunken cowboy in a bar, to a boat trip down the river in the dead of winter to catch a band of boat thieves, Roosevelt not only dressed the part, but he played it as well and he certainly honored his wild.

Final Thoughts

I believe for Roosevelt, dressing the part he intended to play was akin to scaffolding; having a frame of what it was he was trying to become before becoming it. And really, I believe it is the most natural way for us to go about it. Warriors of old wore their masks, headdresses, and terrible colors, often mimicking the fierce animals of the wild in hopes it would provide them courage when the moment of battle arrived. Hopeful athletes, the couch to 5K crowd and the like, are spurred on by a new shirt or pair of shoes. Often, what we wear, the things we buy and keep about us, says a lot about our intent and direction, which speaks volumes about our character. The question we should be asking, then, is not whether we should buy the old axe, the tough boots, the rugged shirt, but how we will become the type of person worthy of such things.