For men who wish to dress better, the first cardinal rule anyone learns is to avoid black. Black suits are for morticians and Model United Nations representatives. Black shirts are for magicians and cruise ship DJs. Black shoes, at best, are for suits and eveningwear. In fact, giving up square-toed black shoes in favor of more anatomically correct brown ones became something of a rite of passage for well-dressed men twenty years ago. And in binning those shoes, many have learned to avoid black entirely.

The thing to remember is that color has a rich and complex social meaning outside of traditional rules. Throughout the 19th and 20th centuries, black has come to signal arrogance and evil thanks to its association with anarchists, motorcycle rebels, and fascists. At the same time, it’s the color of humility and discretion. Think of how Quakers and Orthodox Jews have wrapped themselves in black in order to show their religious devotion. Additionally, writers and poets during The Beat Movement made black an intellectual color; designers such as Givenchy and Armani made it cool and cultivated.

This nuanced appreciation of color is natural in womenswear, but it can take a while for more traditionally minded guys to think outside the box (or, at least, it did for me). Black footwear is de rigueur with navy and grey suits, and you wouldn’t want to wear anything else with a tuxedo. However, black can also be great for casual days. Black nicely complements colors such as navy and green, largely because of how those combos are associated with the military. With other black pieces, black can also look austere and chic. And in certain styles, such as Gucci’s horsebit loafer, black is simply iconic.

For casual footwear, I find black works great in boots. Especially for this time of year, when you’re pushing your way through slush and rain. Some suggestions on how to wear the color across a range of wardrobes styles, from classic to rugged to contemporary.

The Classic Black Boot

If you have a more classically rooted casual wardrobe, black military and field boots can be surprisingly useful. The style goes easily with military inspired outerwear such as naval pea coats, olive field jackets, and anything you might pick up from brands such as Nigel Cabourn. Air Force men, naval officers, and army recruits, after all, all wear black footwear as standard issue. Classic brands such as Alden, Edward Green, and Tricker’s can be perfect for this sort of thing. I also have a pair of Heschung Panax boots that I find goes with nearly everything except tailored clothing. It looks like they’re almost sold out at the moment, but these Carlos Santos field boots look similar.

The Beatles also helped popularize the Chelsea (or rather, their version of it, which had a higher and forward pitched heel). You can wear a pair of elasticated Chelseas with everything from navy suits to grey flannel trousers and charcoal topcoats. Black chukkas and jodhpurs can also be used for the same effect, although I find I reach for Chelseas more often (at least in black). For a pair of solidly built Chelseas on a handsome last, check RM Williams, Crockett & Jones, JM Weston, and Carmina (the last of which is an advertiser on this site).

The Rugged Work Boot

Brown seems like the more natural color for workman boots, and it is, but black here can also make a rugged outfit feel heady and dark. Punks, after all, adopted black Doc Martens in the ‘70s and ’80s as part of their rejection of the corporate class. Black boots make for a terrific pairing with jeans and black double riders, French chore coats, and ranch-inspired outerwear.

For a classic and time worn style, see Red Wing’s Beckmans and engineer boots, as well as the more affordable alternatives from brands such as Blundstone and Thorogood. All four are great for a more basic version of workwear that make you look good without necessarily attracting too much attention. If you’re up for a splurge, Viberg also makes really nice WWII-style service boots, which take after combat boots the American government used to issue to soldiers. You can find black versions of Viberg’s flagship boot at End, Division Road, and the company’s own site.

There are also more re-imagined styles, such as the combat boots you can find from Visvim and Neighborhood, as well as the mid-century camp boots at Yuketen. Some of my favorites right now are from Preziada, which are modeled after something shepherds used to wear in Sardinia. The uppers are made from a matte, full-grain vachetta leather, while the flat rubber sole is thick and chunky. The facings overlap, which gives the boot a unique appearance, while the tongue folds over the top. I love how they look, but the overlapping facings can make the boots a bear to put on. To help, ask the company to send you a longer pair of laces. That’ll allow you to open up the boot a bit more easily and slip your foot in. A video of Preziada’s boots can be seen at the end of this post.

The Contemporary Black Boot

Black shoes can be limiting if you mostly take style inspiration from Southern Italy and 1960s college campuses. That said, they’re incredibly useful if you have anything in your closet that leans a bit more contemporary – lambskin leather jackets, trim grey wool trousers, slim black jeans, and loose topcoats. I mostly wear my black Margiela side-zip boots, but the quality of their shoes leaves a lot to be desired (so it goes with designer footwear). That said, I love their shape and design, and you can find the current season’s Margiela boots at Totokaelo and SSENSE.

Alternatively, you can work around the build quality by getting something in black suede, which won’t crease as badly as cheap smooth leather. Those can be had through Common Projects and Lucchese. Black Chelsea boots, such as those mentioned above from brands such as Carmina or RM Williams, can also be great. The quality on those will be heads and shoulders above from anything you’ll get from a designer brand, although the elasticated sides will give the boots a slightly different sensibility. For something a little chunkier, try Common Projects’ Combat lace-ups.