Boots On The Ground - Finding Boots For Every Season

As winter bears down, we’re hoping you’re not left out in the cold when it comes to exploring the merits of boots. Sure, they’re the perfect footwear for the cold and weather but there’s also a style for every season. With dozens of different types of boots out there, it serves as an advantage to know which ones will best suit your style, while providing the longest shelf life for your wardrobe.

Let’s break down your best bets for each season, and supply you with some primo advice on taking care of your footwear, from shoelace to sole, and everything between.

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. 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.
- Don’t be afraid to beat them up, they can take it, the patina and scuffs that develop add character and look great.

With the cold weather and snow/rain in the forecast, it’s a natural time to lace up a rugged pair of boots. In terms of function, stick with a boot that provides a solid grip and waterproofing (existing or applied by you) to help navigate the slushy city streets. Depending on the look you desire, a rugged hiking-style boot or heritage-style work boot are what you need. Rugged and ready for the seasonal punishment, it’s no wonder this flavor of boot is popular with mountain climbers, site workers, and urban adventurers alike.

Pro Tip: When preparing your boots for a season of storage, be sure they’re completely dry, oiled, and deodorized beforehand. If you have the space, store them upright, in a plastic bin, with your heaviest boots at the bottom.

Depending on when the snow officially stops falling in your neck of the woods, more rugged varieties of boots can still be worn well into early and mid-spring. In warmer climates, the Chelsea boot and captoe boot are great choices when slimming down (and lightening up) your wardrobe for the season. In terms of wardrobe, match the sleeker style of boot with equally trim suits, denim and chinos. These less-rugged styles of boots also take well to a dressier level of attire, so don’t feel like you need to pull out the flannel every time you’re thinking about rocking your boots.

Pro Tip: The dressier the boot, the higher level of difficulty so put some thought into the look. That doesn’t mean you shouldn’t wear them with everything from denim to a suit though.

Depending on where you fall on the map, it’s hurricane season, the average temps feel like standing on the surface of the sun, or a punishing combination of both. (Ok, fine, it’s a perfect 80 degrees in SoCal.) Regardless of your situation, now is the perfect time to don a boot. We recommend your lightest boots, something with a rubber sole and a sleek design. A classic desert boot in a soft suede is versatile enough for all varieties of dress and can even be paired with shorts.

Pro Tip: Stick with lighter colors, as well as softer leathers, suede and canvas (if possible) to beat the heat. Also invest in a good deodorizer or foot powder, especially if you’re prone to walking a lot.

Arguably the best time to break out some boots, because it’s neither too hot nor too cold, fall is the time for boots that are a mix of chunkier and sleeker soles and styles. Chukka and desert boots are the perfect transition as the weather cools as they provide a good balance between style and substance. In fact, if there is one season in which you can truly wear all styles of boots, Fall is it.

Pro Tip: This is the time of year when your boots are probably going to get the most use, so be sure to take extra care of them, from periodic conditionings to lace and eyelet replacements, if necessary.

A Word On Wingtips
Think of a well-constructed, leather wingtip boot as you would the navy suit, Oxford shirt or tailored chinos: an instant classic. Known for the ornate stippling, or “broguing”, found around the toe and vamp, styles vary and some can be as dressy as your office wingtip while others with a rugged lug sole can dress way down. As we discussed in the past, these boots work exceedingly well with all types of suits. Of course you can also dress them down considerably with denim or cords and a comfortable sweater, or a crisp t-shirt and selvedge jeans. The key point to keep in mind is the brogue detailing is going to give them a bit more of a dressy feel than your other boots, that’s what makes them so versatile. Your options are virtually endless. Just remember to treat them with the same care you would any other leather shoe, and they’ll last you a long time.

Hopefully we’ve shown you that boots don’t have to be treated as merely a utility that you dust off every time the rainy season comes around. Consider this proof positive that boots--of nearly every style--should have a prominent place in your closet’s roster, all year round.

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