Fall Footwear Reboot

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Fall's arrival signals an exciting time of year for your wardrobe. After months of T-shirts, shorts and polo shirts, the options suddenly become much wider. Shirts and pants become more structured and detailed, and interestingly textured sweaters and jackets make their debut. But no matter how well you plan your seasonal wardrobe, all could be lost if you don’t select the right footwear. Your feet may be at the southernmost tip of your body, but don’t make them your last priority: A great pair of boots is a valuable asset in any man’s wardrobe.

A simple mid-height leather boot would look perfect with a suit, or with nice jeans and a blazer.

Patrick Buchanan, social media coordinator at Creative Recreation

Rugged or Refined?

One of the most important factors in selecting the right pair of boots is familiarizing yourself with the different styles available. Within the abundance of options, you’ll find that boots mostly fall into one of two categories: rugged or refined.

“The treatment of the material is a huge factor,” said Brooke Hyden, style expert at Zappos.com. “If it's worn or distressed, it's more rugged. To be more refined, go for a pair that's more polished.”

“A rugged boot looks worn or broken in,” advised Patrick Buchanan, social media coordinator at the shoe company Creative Recreation. “Cowboy boots and combat boots always give a rugged look. Refined boots are defined by a nice, smooth leather and hard bottom.”

The thickness of the sole is also a major indicator. Thicker soles always denote a casual boot, while thinner soles are reserved mostly (though not exclusively) for more formal footwear.

Going Casual

When selecting footwear for use during your downtime, pay close attention to your dressed-down style. A casual boot will not automatically go with every casual outfit you own. “If you have a pair of slim jeans that you want to keep trendy by tucking messily into boots, make sure to look for a pair that lace up, so you can leave the top open,” Hyden suggested.

And aspiring rockers can go a little further. “For the ultimate rock-star look, pair your combat boots with skinny jeans,” said Buchanan. “They don't have to be skin-tight, just a great fit that not only shows off your figure but showcases your boots.”

Of course, some of us don’t boast the rock-star bodies – or tastes – necessary for skinny jeans. Rather than force a style that may not work for you, consider other options. “Boot-cut jeans pair well with cowboy boots,” advised celebrity fashion stylist Arturo D. Chavez. “(Additionally,) round-toe ankle boots are a great casual everyday boot. … They really go well with everything.”

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Smartening Up

Boots aren’t just for rugged types; the right pair also can prove to be a surprisingly sleek addition to a formal ensemble. “For a more formal occasion, you need a nice round-toe, hard-bottom boot,” said Buchanan, who cautions against wearing square-toed footwear. “A simple, mid-height leather boot would look perfect with a suit, or with nice jeans and a blazer.”

“A pointy or narrow ankle boot can be dressed up and paired with suits,” Chavez suggested, noting the universal appeal of the boot: “Tuxedos are the only time I don't see boots being appropriate.”

To achieve the best results, go for a clean, polished leather: “Look for a pair of loafer-type boots in a patent leather,” Hyden said. “This will look modern and stylish, but still formal and classic.”

If you want a boot that works well for the office as well as a night out on the town, find one that comfortably straddles the line between being somewhat smart and casual. For extra versatility and dress-down appeal, Hyden recommends the desert boot. “(Desert boots) have made a big comeback,” she said. “They're perfect with jeans for a more relaxed look.”

Maximizing Comfort

Consider how long you’ll wear your boots each day and what you’ll do in them. Outside of extreme situations, temperatures tend to be fairly mild during the fall season. As such, going very bulky, or opting for high-top boots, could well leave you with sweaty feet. Unless your personal style dictates otherwise, go for mid-length boots, although high-tops are proving popular in the boot/sneaker hybrid market.

And while your feet may have enjoyed a summer of partial exposure, fall marks a time when you should rekindle your relationship with a few good pairs of wool socks. Not only will they help prevent blisters, they'll also aid the fight against the smelly boot factor (which mitigates any style points you earn).

Boots: Year-Round Footwear

One of the biggest misconceptions about boots is that they should see light of day only during the fall and winter. While it’s certainly the case that footwear suitable for trekking in the snow has no place at a summer barbecue, there are still boots that deserve to make an appearance, no matter what season.

“Honestly, there is almost a boot made today for every outfit,” said Brooke Hyden, style expert at Zappos.com. “A great pair of chukkas can even be worn with shorts."

“For the warmer days, find a lightweight boot,” advised Patrick Buchanan, social media coordinator at Creative Recreation. “I always wear my boots for a night on the town, no matter what the weather. The only time I wouldn't wear my boots is during my weekend trips to the beach or hanging by the pool.”

“I have pairs of brown and black round-toe ankle boots that I wear year-round,” shared celebrity fashion stylist Arturo D. Chavez. “The more I wear them, the better they look and the more compliments I get. They go with everything.”