Bill Weld: the latest in Libertarian chic

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Bill Weld

Quirky, idiosyncratic and one-of-a-kind… just a few of the adjectives that have been used to describe the former Governor of Massachusetts, Bill Weld. He may be unusual in his approach, but for this Libertarian politician, it’s simply all in a day’s work.

He’s known for his curious – some would say unpredictable – behavior. Take the build up to the 2008 presidential election. In his time as the Governor of Massachusetts from 1991 to 1997, Weld was a well-known Republican. Then, in October 2008, came an unprecedented move – Weld went on the record to publicly endorse Barack Obama, a Democrat, as his choice for president. Fast forward to 2016 and Bill Weld would make a dramatic exit from the GOP to join the Libertarian Party. What was his reaction? “Free at last. Free at last!” he said to an expectant crowd from his new party.

That was the beginning of what turned out to be a historic but roller-coaster first year with the LP. In the 2016 election, As the running mate to Gary Johnson, the duo became the first presidential pairing since 1948 to consist of two former governors. The Libertarian ticket garnered four and a half million votes as the party’s vice-presidential nominee – a record result for the third party.

An unexpected accomlishment, but hardly surprising from a man who has been known to write thrillers and historical fiction in his spare time. Another fun fact: Weld’s first wife and mother to his five children just so happens to be the great granddaughter of Theodore Roosevelt.

Bill Weld certainly is a man in a million and, we’ve come to realize, no slouch in the fashion stakes either. We’ve dug up some stylish shots from his time in the spotlight and rate our best picks.

Gary Johnson and Bill Weld – A Dapper Duo


Snapped in the build up to the 2016 election, Bill Weld and Gary Johnson would certainly get the vote for best style. Weld in particular shines in a pinstriped navy blue suit and a contrasting bright red tie. Johnson, on the other hand, took the title of running mate literally – seen here in his finest sneakers for the shoot.

A Meeting of the Minds


For a TV appearance alongside his Libertarian running mate Gary Johnson and Starbucks CEO Howard Schultz, Weld pulled out his suave Sunday best. Kitted out in a suit of dark navy blue, he cuts a dashing figure alongside his equally sophisticated fellow guests.

Comfortable Chic


Listen, it’s not difficult to make a suede leather jacket look good. Weld posted this throwback picture to his Instagram feed of his time at Freedom Fest, a meeting of independent free thinkers held in Las Vegas each year. In this easy-going outfit of blue denim jeans, a white button-down shirt and a leather belt, he certainly fits the easy-going bill.

Tour de Force


What a stylish team they make! Here Weld is seen exploring the streets of Boston with Gary Johnson back in 2016. The running mates share similar ensembles of dark blue jeans and easy blue button-down shirts. Understated and effortlessly suave!

Talk Show Triumph


The dashing duo strikes again – this time as guests on Stephen Colbert’s political talk show. Primed and poised in style, Weld’s choice for the event was a faintly striped suit in deep midnight blue worn with a pale blue shirt and a polka dot tie. Johnson meanwhile stayed committed to his comfortable footwear choice: running shoes. Quirky and just a little eccentric – we’d expect nothing less!

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