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The countdown is on. Labor Day has come and gone, and summer is more or less in the books. That means it’s time to start thinking sweater weather—and trading your flip flops and sandals for decidedly more practical fall-friendly footwear. This year brings with it plenty of styles that are both approachable and fashionable, two often mutually exclusive concepts that can trip up anyone who wants to emulate something they spotted on the runway. We’ve rounded up a handful of shoes that aren’t just comfortable, but also easy to wear and integrate into your cool-weather wardrobe.

Thursday Boot Co. Scout

If you’ve never met a chukka boot you didn’t like, you’ll be smitten with the Thursday Boot Co. Scout. It’s the epitome of the iconic style known for its rugged-gone-refined appearance. Available in an array of colors ranging from dark olive suede to brown, this handsome shoe is made with durable leathers and suedes that are designed to stand up to regular wear. The interior is lined with glove leather for a smooth feel, while shock-absorbing insoles make your trek from the train to the office a little more manageable. Style them with anything from dress pants to jeans for an easy choice all season long.

Nike Air Force 1 Crater FlyKnit

The definition of sporty, modern style, the Nike Air Force 1 Crater FlyKnit puts a fresh spin on an old favorite. This legendary kick is no stranger to basketball enthusiasts, but the newest iteration is more than worthy of becoming the ultimate crossover. Its eye-catching Crater foam contributes to its light-as-air feel, while the lightweight upper offers a smooth finish. So effortless and relaxed that you might forget you’re wearing it, it’s a great choice for your weekend b-ball game, your errand run, or your morning workout.

Converse Jack Purcell Leather

Some shoes are so classic, they deserve all the accolades they receive. That’s unarguably the case with the Converse Jack Purcell Leather, a sleek and stylish shoe that made its debut in the mid 1930s. For Converse devotees, the shoe’s history is legendary: badminton player Jack Purcell teamed up with B.F. Goodrich, the former rubber manufacturing giant, to create a sturdy and durable court shoe. The result was what was dubbed “the big shoe” thanks to its bold wedge designed to provide greater stability and shock absorbency. Those traits remain today, making it a true icon for both sport and street wear.

Nisolo Cortex Mid Top Sneaker

Sometimes you just want a little extra coverage. You’re all about that sporty sneaker, but you don’t necessarily want to wear a pair of high-tops either. Nisolo Cortex Mid Top Sneakers offer the perfect middle ground—with a dressier edge. These striking shoes capture the laid-back appeal of your favorite kicks, giving them a more refined spin courtesy of a waterproof leather upper and a smooth-like-butter lining that’s sure to make every step a dream. Durable materials, like a sturdy rubber outsole and robust laces, contribute to a shoe that’s flawless inside and out.

XTRATUF Men’s 6 In Legacy Chelsea Boot

When temperatures start to plummet, the winds pick up, and the forecast begins to look decidedly less pleasant, you’ll be glad you snapped up a pair of XTRATUF Men’s 6 In Legacy Chelsea Boot. They live up to their name, promoting the kind of stability you desperately want when you’re sloshing through puddles and making your way to your destination in the middle of an unpredictable storm. The waterproof boot is made with smooth leather and features a slip-resistant outsole that will keep you safe while you’re en route. It’s even suitable to wear in factories and other professional environments thanks to its acid- and chemical-resistant design.

Astorflex Patnoflex

This is no ordinary loafer. The Astorflex Patnoflex is the type of shoe that appeals to true sartorial types—and those who simply appreciate good fashion. The shoe, handmade in Italy, is made with leather that’s aged for at least a month in a combination of water, oak bark, and powdered mimosa (the root, not the brunch beverage). The natural concoction lends the shoe its incredibly handsome finish, while exquisite workmanship sets it apart from other dress shoes in your closet. It feels so soft you might think you were wearing a pair of slippers, and it’s so versatile you’ll want to wear it with everything from khakis at the country club to corduroys on dinner dates.

ON Cloudnova Shoe

Pavements can be unforgiving at the best of times. When fall comes around and wet weather is more of a possibility, it’s important to protect your feet with high-quality sneakers that are durable, flexible, and supportive. Enter the ON Cloudnova Shoe, the ultimate running shoe for avid workout enthusiasts who appreciate the feel of plush clouds underfoot. You don’t have to log multiple miles a day or hit the gym to make good use of these kicks, though. A walk around the neighborhood or an errand run is just as good an excuse.

Whether you’re seeking an athletic shoe, an all-weather or a wet-weather boot, or a dress shoe, you’ll find plenty of flattering choices this fall. Each makes an easy companion for your wardrobe throughout the season.

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