If we ever meet in person, and I am not wearing a suit, chances are I will be wearing jeans with black boots.
Back in 2012, I got my first pair of Cole Haan boots, similar to this pair, for a February trip to New York. I didn’t purchase them to wear in the snow, but when an unrelenting storm blew through the city, I had no choice.
Needless to say, I wore them out. But neither the snow nor the messy streets of NYC could damage them. They were indestructible.
Ever since then, I’ve been obsessed with boots—particularly black ones—for their resilience to wear and their infallible versatility. And these days, I have a collection of them that I wear almost daily.
Now that Fall is upon us and boots are widely available in every store, it’s time to check out the best options for the season.
Here are my picks—and why.
Round toe, two-tone pull loop, soft leather. If ever you were to wear black boots with something other than an all-black outfit, these would be the boots to break the rule. Pair these with some navy cotton trousers and a light gray sweater for a modern feel.
These boots were made to wear with denim. Everything from the distressed suede to the Cuban heel to the serious point on the front makes these bad boys the equivalent of a middle finger to traditional boots. Pair these with some stone-wash denim and a loose, long t-shirt, and you’re ready for some underground music and trendy gin.
When I think of Chelsea boots, this is what I see. Sleek, buffed, classic. Saint Laurent is hands-down the very best in the game, which is why it appears twice on this list (see number 4). Pair these with virtually anything, and they’ll hold their own.
Yes, that’s correct. Saint Laurent has multiple versions of the same boot, however unlike the previous version, this one is a bit higher and includes a criss-crossing ankle strap. I would live in these boots if I could. Pair these with shredded black denim, a new white shirt and some killer rings. Because, why not?
Yes, I know these are “a look,” and I agree. But to be fair, when is Versace not a commitment? In order to rock these, you cannot wear anything other than all black. No exceptions. I recommend you wear these with this discontinued Bodaskins leather jacket in oil black.