Don’t kill the messenger, but summer is coming to an end. You probably don’t need me to tell you this because you know how a calendar works. Still it’s never easy to say goodbye to summer and get back into the more serious vibe of regular life, which is devoid of abbreviated Friday hours, beach days, and BBQs. But if there’s a silver lining to the changing seasons, it’s that the arrival of fall means you can flex your sartorial muscles a bit more.
Summer style is great, primarily because it’s so simple. White T-shirt, shorts, and some fresh kicks and you’re good. Fall is a chance to mix things up a bit more. That starts from the ground up with the right shoes. You may be able to get away with rocking flip-flops when the temperatures hit triple digits, but you you’ll need more coverage come September. To get you ready, here are the five shoes every guy needs this fall.
THE CHELSEA BOOT:
Popularized by the cool kids (e.g. the Rolling Stones) in the Swinging London days of the 1950s and 60s, the Chelsea boot is enjoying a revival. Kanye West has been stepping out in them recently, which is either a good or bad thing depending on your view of ‘Ye. Regardless, with its elasticized sides, the Chelsea boot has a sleek, pulled together look that pairs perfectly with a pair of slim (or tapered) jeans or pants.
THE PENNY LOAFER
Cole Haan, $140
The penny loafer has been a preppy staple almost as long as there have been prep schools. To give it a more modern and urban vibe, go with a black pair. They look great with a pair of beat-up blue jeans and a white oxford shirt. To update its classic design, Cole Haan added a Grand.OS cushioning system and a rubber outsole (with a clever lobster logo) to make them way more comfortable than the stiff pairs you may remember.
THE RUNNING SHOE
New Balance, $249.99
Just as the leaves change color as the seasons shift, so should your sneakers. Summer is all about pristine white kicks, but come fall it’s time to expand the palette to include earthier tones. These classic New Balance running shoes are made in the U.S.A. using leather from the Chicago-based Horween tannery and the colorway is inspired by the mid-century modern design movement.
THE BROWN WINGTIP
Johnston & Murphy, $155
The beauty of the wingtip is its versatility. You can walk into the most buttoned-up corporate boardroom and feel confident you’ve got the right footwear on. But a wingtip done up in a lighter brown leather also dresses down easily. Wear them without socks (you can still get away with that in the fall) and some pants hemmed to fall right at the ankle and you’ve got a sharp look for a Friday night out.
THE DESERT BOOT
*Clarks, $140 * The desert boot is another shoe that goes from work to whatever-you-do-after-work with ease, which is why it’s known as the first dress casual shoe. Clarks founder Nathan Clark discovered a version of the shoe while he was stationed in Burma with the British Army and created his own version of the shoe which he revealed at the Chicago Shoe Fair in 1949. With its comfortable crepe sole, it’s become an icon. The sand suede or beeswax leather versions are classic, but you can add a subtle pop of color with this wine suede version.