Fall/Winter Style Guide: Boot Up

Title: Fall/Winter Style Guide: Boot Up Welcome to the Unhemmed Fall Style Guide! Dressing seasonally and prepping for cooler temps doesn’t have to be difficult, and with our help you’ll be looking stylish and feeling confident just as the leaves are starting to turn.

First, it’s time to boot up. No, no, we’re not talking about cowboy boots. Don’t get us wrong, there’s nothing wrong with ‘em, but let’s just say...it takes a man with a particular look (and a special set of courage) to pull them off properly. No, we’re talking about boots for the everyman. Not just for mountain ranges, campfires and construction sites, boots come in a variety of stylish flavors and are the perfect step outside of the (shoe)box when the weather cools.

Before we discuss options, let’s start with a few guidelines to get you off on the right foot. (See what I did there?)

  • Invest in quality. Great boots are a pair of shoes that can last you years if you find the right ones.
  • Patience my friend, patience. Heed the words in the Guns ‘N Roses song, it takes time to break in a good pair of boots. Stick with it, your patience will be rewarded.
  • Learn how to properly care for you boots. Suede and leather need a little extra TLC, so waterproof them for those rainy and snowy months. There are several ways to do this, just be sure to do it regularly (that means every few months if you live in extreme weather conditions).
  • Don’t be afraid to beat them up, they can take it, the patina and scuffs that develop add character and look great.

With that in mind, we recommend looking at three types of boots as you start to build your collection. They all have their individual merits but most importantly, they’re all very versatile. They all can be dressed up or down with ease and any pair will get you through the season in fine form.

Desert Boots Just dipping your toes into the boot pool for the first time? Welcome. We recommend starting out with a pair of Desert Boots. Originally designed for the British Military to be worn on (you guessed it!) desert battlefields, they commonly feature a crepe rubber sole and are lightweight and very comfortable. Available in suede or leather options, this is an outstanding boot to start out with because of it’s immense versatility. Wear them with jeans and chinos and dress them up or down to your liking. Add a button up and a blazer for the office or a night out, or just throw on your favorite selvedge, a cardigan, and a t-shirt, it all works with your desert boots. (Caveat: We cannot guarantee the badassery of a British soldier will come to you just by wearing this shoe.)

Work Boots From the factory floor or work site to your closet. Work-style boots are strong, long-lasting and definitely a step up in the style department. Embracing America’s rich manufacturing heritage and a rugged outdoors-y sensibility, you’ll typically find them with two different sole variations, a lug style (like tire treads) or wedge style (a single wedge shaped sole piece). They also come in both round toe styles and moc toe styles with a two-piece, stitched toe. The perfect style of boot for everything Mother Nature can throw at you, these boots, when properly broken in and cared for, are the stuff of legends. I mean, our country was, and still is, built on the backs of these sturdy shoes, it’s almost your damn patriotic duty to own a pair. That you’ll look super stylish in them is an added benefit. While not as dress up-capable as a pair of desert boots, a work boot pairs equally well with denim, chinos and a variety or casual wear.

Dress Boots Boots with dress clothes you say? Indeed my good man, indeed. Featuring many of the characteristics of your favorite pair of wingtips or captoes, a dress boot adds an interesting mix of elegance and character to your dress clothes. Things to keep in mind when considering a dress boot...you want to avoid any that are overly round, chunky or “outdoorsy”. That means anything with a lug or tread sole; you’ll want something a sleek profile and the polish of a dress shoe. We recommend starting with a wingtip boot, it’s a great middle ground and can just as easily be worn with your favorite suit and an overcoat as it can with a crisp pair of selvedge denim and your favorite sweater.

That’s it, your boot game is on lock and you’re ready to face the mean streets of fall and winter like a well booted gentleman. Expect compliments.

Shop