It doesn’t matter what the weather does, the first days after Labor Day just feel different. The temperature can still exceed 90 degrees with 90 percent humidity, but mentally you cross the threshold into fall—and there is no turning back. The concept of “back to school” is so deeply ingrained in our psyches, even if it’s been decades since we stepped foot in a classroom.
That mentality carries over into style. While the days of buying a new Trapper Keeper and protractor with your mom have passed (do kids these days even use paper?), you can still cop some back-to-school clothes. The only difference is now you have to pick up the bill yourself. The best way to transition into fall style is from the ground up. It’s time to put the sandals away (please don’t try to prolong the season by wearing them with socks!). And there’s no better pair of shoes to replace them with than a pair of Chelsea boots.
Originally created by Queen Victoria’s bootmaker in the mid 1800s, the ankle-high, elastic-sided Chelsea boot evolved into a mod rocker staple favored by members of the Rolling Stones and the Beatles a century later. The Chelsea boot even made an appearance on the feet of Stormtroopers in the original Star Wars trilogy.
The slip-on design gives the boots a sleek look that is as polished as a dress shoe, all while retaining a cool, downtown vibe. They can dress up a pair of faded, broken-in jeans or add a cool factor to a traditional suit. And because they aren’t as chunky as work boots, they work well with slimmer pant silhouettes.
To help you adjust to fall, here are six pairs of Chelsea boots that will make you less sad that summer is over.
Jack Erwin has carved out a nice niche for itself, producing classic men’s dress shoes with the same quality and style as those from luxury houses for about half the price. Jack Erwin’s Chelsea boot is a perfect example. It has the familiar slim lines and suede upper, and sits atop a rubber sole for added comfort.
If ever there was a shoe that could rival Common Projects’ iconic Achilles sneaker, it’s the brand’s Chelsea boot. After they quickly sold out when first released, Common Projects only stoked demand by releasing fresh new colorways. They have the gold foil stamp on the heel and feature a crepe sole that is ridiculously comfortable (and keeps the boots from becoming too formal).
Dr. Martens’ original combat boot needs no introduction. Docs have been popular among creative types, from musicians to artists, for decades. The brand kept the soul (and the sole) of those originals but transformed the upper into a Chelsea boot for a clever spin that stands out from the pack. No animal products are used in constructing the vegan boots, which have the famous AirWare Bouncing sole. The oxblood color is about as punk rock as things get.
Looking at A.P.C.’s Grant boots from the outside, you would never know that the person wearing them is as comfortable as he is in his favorite slippers. The calfskin uppers are lined in fluffy sheepskin that makes them extremely cozy. But unlike the Hollywood celebs we see in sheepskin-lined Ugg boots, these maintain a polished look that is appropriate for every occasion.
If you want the look of a pair of Chelsea boots but can’t bear to be without sneakers, Zara has the perfect hybrid option. The elastic sides on the upper are less pronounced and the vulcanized sole is reminiscent of a pair of skate shoes. Every guy needs a pair of “dress sneakers” and these fit the bill well.
Prada’s take on the Chelsea boot is best described as “modern mod.” The foam soles are thicker than most, which gives the shoes a more futuristic feel while the leather on the upper is incredibly smooth, which adds to the sleekness.