Last Updated on 10th December 2008

The Good

John Legend may have eschewed all levels of style etiquette by venturing out with a suit complete with Wellingtons, but please don’t let his missteps lead you to cast a finicky eye over the trend. Unfortunately Mr. Legend didn’t get the memo, but keeping one’s Wellingtons away from the red carpet is a no?brainer.

As a child I had that lone pair of Wellingtons I trudged to and fro to school in, but once the pitter-patter of winter’s rains dissipated, I never really looked to gumboots as a stylish auxiliary. My partiality to see Wellingtons as a silly trapping continued into adolescence and began to extend to all four seasons. Whether it was raining cats and dogs or, in the case of Mr. Legend, not even drizzling a lick (in southern California), I had arrived at place where you would never have caught me dead in a pair of Wellingtons.

Then Glastonbury came, followed by GANT, and I began to reassess my leanings on what seemed to be the highly sought after Wellington. Was I being over critical about John Legend’s get up? Not in the slightest. The mishmash was just too much of an insult to my visual senses as Legend un?heroically paired the outdoorsy with formal. Stay with that point.

On the contrary, as I clicked through Material Interest’s photo-documentary on Glasto fashion, I realized that the jaundiced eye that I had glaringly cast over Wellingtons, as a whole, was a tad presumptuous. Amid the backdrop of a marshy, rain?bogged music festival like Glastonbury, Wellingtons stylishly foot the bill. Even the recent Sartorialist?inspired GANT fall ad campaign featured a rather spiffy looking Brooklyn hipster decked out in wellingtons. As removed as a concrete Brooklyn stoop is from the pastoral terrains of Glastonbury, the Wellies don’t look one bit outlandish. Moreover, the fall/winter months are marked by the occasional downpour so, in retrospect, investing and strolling about in a pair of wellingtons may not be a stylish faux pas like some (myself included) may think.

I do happen to draw the line, however, when suits, blazers or other proper modes of dress are thrown into the mix. When a scruffy gumboot is mirrored next to a sports coat, the polarity is a trifle too much to take in….

The Bad

especially when one’s jacket is not even fitted….

The Ugly

And the moral of the story is this – when pairing Wellingtons for fall, rock them with understated outerwear like a cardigan, leather jacket or a hoodie and leave the blazer at home!


This page may contain affiliate links. We may receive a small commission when you click an affiliate link and make a purchase. This helps keep My Fashion Life running so we can provide you with high-quality content regularly. Thank you for your support!