Everyone likes a good boot and with Spring on the horizon, now might be the right time to pick up a new pair with end of season sales. I think that it’s safe to suggest that boots occupy a special place in the hearts of those with a deep shoe obsession. Among the most dedicated shoe aficionados, developing a profound fondness for boots – or maybe addiction is a better word – is perfectly natural. As one becomes enlightened and learns to invest in attractive quality shoes, building a top notch boot collection will eventually become the foundation of your fall/winter wardrobe.
Indeed, there's a strong argument for the supremacy of boots, beyond saving your ass when you forgot to do laundry leaving you with white gym socks. When you think about it, the additional construction complexity and design details create more space for eye catching styles and unique details. Or maybe for someone who really just loves shoes, the math adds up: boots equal more shoe. I for one like to believe that the passion for boots comes from a sense of function tied to the past. Historically, boots are purpose built; you've got riding boots, hunting boots, snow boots, and even moon boots. This means that putting on boots can be a somewhat transformative experience, changing the way you feel, similar to putting on a nice suit.
Since boots aren't usually regarded as a replacement for regular dress shoes and are more expensive, you probably won't add them to your collection as fast as your other footwear. So it's important to put some thought into how and when you might wear them. To that, read more about some key boot styles below and how to style them.
The chukka definitely takes the podium for versatility, and may be a perfect choice if you had to pick one style to start a collection. While the few and high up lacing eyelets create an elongated classy effect, the derby lacing keeps them a bit fun. The result is that they work just as well with blue jeans and a flannel shirt as with a suit and tie.
Chukkas are right at home when something smart is called for, but you don’t want to come across too formal. My suggestion is to try them with white jeans, luxury knitwear and subtly patterned sportcoat. Or to add some character to a classic business vibe, go with a finely tailored navy suit, gingham shirt and knit tie.
Bold desert boots
While this may not be your first choice if you're looking for an office worthy boot, a playful desert boot in a bold colour is a great addition to your boot game – especially for those casual Fridays. A boot like this will show you're not afraid to stand out.
A unique coloured suede boot is a bit quirky, so try something a little less serious, like neutral chinos, a denim shirt and a waistcoat or a chunky cardigan. The trick to tastefully highlighting a bold colour boot is to avoid aggressive clashing or too much colour. For example, green chinos would not be a wise choice for the Burgundy boots I’m wearing here.
Chelseas are definitely the most popular boot style out there and for good reason. Most types of boots have some lineage to the past, and Chelseas are no different, yet they are somehow always modern and never out of style.
This one is a no brainer - a sharp black Chelsea will back up any look so pair it with a henley, a well fitted leather jacket and blue jeans or grey chinos.
Easily distinguished by the angular lines and the buckles, and as the name suggests, this boot was supposedly developed in Jodhpur, India after the invention of the Jodhpur pants, which eliminated the need for knee high riding boots.
A boot like this is an understated classic boot with Equestrian history, so step back in time and dress them up with a timeless jacket and tie - we've all had more than enough of skinny jeans and "invisible ties".
There’s nothing worse than someone else showing up to the party with the same boots – gasp! Luckily and easy way to avoid said catastrophe is go buy a pair of monkstrap boots, unless James Bond is at the party. One thing I really like about the pair pictured is how they are rather dressy and elegant, but also distinctively masculine.
A special boot like a monkstrap deserves some airtime to show off, and what better way to showcase it than a simple mid-grey flannel suit and white shirt for a minimalist dressed down suit look that will ensure the boots get the attention they deserve. Lighter tone grey against black shoes creates a sharp contrast while leaving you plenty of options up top.