1.  Franklin D. Roosevelt (third row, second from left)

Before he became the first and last person to run win the office of president  4 times, Roosevelt was a child of privilege sheltered in his family’s home along the Hudson River Valley and later attending Groton and Harvard (Class of ‘04…the other ‘04). He was known as a loveable playboy doning white slacks and straw hats.

Roosevelt (left) as a candidate for vice president, 1920

His preppy style would last well into his presidency. While dining with stationed troops, Roosevelt would wear his pinstripe suit and v-neck sweater and skinny tie. He never pretended to be something he was not.

 ”Be sincere; be brief; be seated.”

2. Arthur Schlesinger

Arthur Schlesinger may appear as the universal stereotype of an egghead, but he was 2nd most gifted historian of the 20th century. The first was his father, Arthur Schlesinger, Sr.

Jr didn’t do so bad himself. He would not only follow his father’s footsteps as a Harvard professor, but would also go on to advise Democratic Party leaders Adlai Stevenson, John F. Kennedy, Lyndon Johnson, and Robert Kennedy. He is the premier historian recounting the policy and politics of the New Deal, Fair Deal, the New Frontier, and Great Society programs.

Known for his bowties, tweed blazers, great taste, Schlesinger could be found in his New York pentouse or a Georgetown drinking parlor. He made it hip to be square.

3. Martin Luther King, Jr.

This iconic leader was the standard for early 60s style. Pocket square neatly folded in the presidential ‘continental’ style, tie clasp, and shined shoes, MLK would’ve made anyone’s top fashion list today. He roughed through the terrains of the 20th century’s biggest challenges with class and style.

Not bad for a guy who graduated from college (Morehouse) at the age of 19.

“I have decided to stick with love. Hate is too great a burden to bear.”

4. George H. W. Bush

The former U.S. President, Vice President, RNC Chairman, CIA Director, UN Ambassador, Envoy to China, Congressman (he’s held every position of power possible, even his son became president)…is no stranger to the Ivy Leagues. A baseball star at Yale (awarded his MVP trophy by Babe Ruth himself) after he served as one of the youngest Navy pilots in WWII, Bush was a member of the secret skull and bones secret society. Most of all, this guy new how to use his prepster and  secret insider connections.

“I’m going to be so much better a president for having been at the CIA that you’re not going to believe it.” 

Club Relaford and George H. W. Bush

5.  Robert Kennedy (bottom right)

Bobby in polo with brother John

This former attorney general, senator and overall Democratic political operator was not known as the most intellectual or athletic in his famous family (he did play defensive end on the Harvard football team), but when it was all said and done, he had escaped the shadow of his older brothers (Jack -above, and Joe Jr.) and was quoating Escalus in his speeches and a force to be reckond with during backyard football games.  And although he was not Mr. GQ, he always wore crisp white dress shirts to the office and despised button down collars.

“I was the seventh of nine children. When you come from that far down you have to struggle to survive.”

6. Bill Moyers

Bill Moyers was not only Lyndon Johnson’s press secretary and chief of staff, but the muse of the hipster movement (even if  he or they know it or not). This native Texan started out in the mailroom in Sen. LBJ’s office and worked his way up, the old fashion way.

“Creativity is piercing the mundane to find the marvelous.”

Club Relaford and Moyers

7. Clarence Page

This stalwart of The Chicago Tribune has been writing for the paper since 1969. He was drafted into the military 6 months into his first gig with the paper. Armed with a journalism degree from Ohio University, Page’s ‘real talk’ writing style and tortoise shell circle framed glasses make you feel a little smarter after picking up the paper.

8. Roby Penn, IV (left)

Ok…so oil executive and foundation head Roby Penn, IV is not a politician per se, but before this Texas native left for the lone star state just recently, he was a business, charity, and all around mover and shaker in DC circles. Always attending or participating in the hottest polo matches, Penn does it in authentic prep style.

9.  George Will (right)

The conservative columnist and Washington mainstay is known for his great taste and love for steroid free baseball.

“Baseball, it is said, is only a game. True. And the Grand Canyon is only a hole in Arizona. Not all holes, or games, are created equal.”

10. Tucker Carlson

The Republican talk show host and strategist attended St. George’s School in Newport, RI. Rocked bowties until he made the life changing decision to switch to neckties full time in April 2006.

“I just decided I wanted to give my neck a break.”