President’s Day Style, part 1 – Teddy Roosevelt

Gabe Alonso Style Editor

In honor of President’s Day this weekend, I thought it’d be fun to honor some of our most stylish Presidents. It takes a lot of work to be the POTUS and looking good while doing it is an added bonus. Who has the honor of being featured first? The OG Rough Rider, Teddy Roosevelt.


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As a lieutenant colonel during the Spanish-American War, he led the charge at San Juan with his famous band of Rough Riders. Upon his return to the States, Boss Tom Platt needed a hero to place in the elections for Governor to draw attention from scandal in New York. Roosevelt accepted and running on the Republican tickets, he won At 43 years old, Theodore Roosevelt was the youngest man to ever hold the Presidency. He stepped into office in 1901 after the assassination of President McKinley. He was an energetic and passionate leader. During his eight year reign as President, he vigorously fought for progressive reforms and continued to expand America’s influence abroad. He was the epitome of one of his favorite proverbs, “Speak softly and carry a big stick.”

Roosevelt’s contributions to American history are numerous. However, one thing he doesn’t get enough credit for is his fantastic sense of dress. Roosevelt was a outdoors-man. He hunted big game, drove cattle, and apparently even captured an outlaw once. The guy was a bad ass. But just because he was the manliest of men, it didn’t mean he skimped on dressing to the nines every day. Admittedly, the early 20th century was a different time, a time when men every where dressed in suits more often than not. Roosevelt was no exception. He could almost always be found in a 3-piece suit with his signature glasses perched atop his nose and that diesel moustache. In honor of him and his Presidential style, I give you an outfit inspired by the former Rough Rider. There’s a bit of refinement with a bit more of rugged.

Dockers Never-Iron Essential Khaki Straight Fiton sale $50, orig. $75

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J. Crew Pinpoint Oxford Club Collar shirt – $69.50
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Lands’ End Canvas Silk Wool Buffalo Check Tieon sale $14, orig. $39.50

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L.L. Bean Signature Bean’s 1947 Field Coat – $185

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Palladium Baggy II Boots – $85

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