Black shoes have gotten a bum rap over the years. As Pete once noted, switching to brown footwear has become something of a rite of passage for men who care about how they dress. Most guys start improving their wardrobes by throwing out the duck billed, black dress shoes they bought in the ‘90s – but in switching to brown footwear, they also give up on black entirely. And maybe for good reason. Brown patinates better and is easier to wear in casual settings. Plus, it’s said that southern Italian men favor brown footwear – and who doesn’t want to dress like a southern Italian man?
Lately, however, I’ve been finding that I reach for black shoes almost half the week. And not just the dressed-up, oxford kind that you might wear with navy or grey suits (although, black is a wonderful color for those more formal occasions). Instead, I like black for casual shoes.
The thing to remember about color is that it’s not just about formality or setting (e.g. navy suits in the city; brown footwear in the country). It can be about emotional and social language. 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 bit loafer, black is simply iconic.
The key to wearing black shoes is to avoid anything that could be mistaken for business dress (unless you are, in fact, wearing a suit). Some styles that I think are particularly useful:
- Black Combat Boots: Probably the easiest to wear. Pair them with olive field jackets or fatigues, or even with slim black jeans. I have a pair from Heschung that I love to wear with a slightly oversized Stephan Schneider coat. Just be careful with some fashion line versions – it’s still better if you can get these in a full grain leather, rather than corrected grain.
- Black Engineer Boots: Great with more traditionally styled workwear, such as the things you’d find at RRL or Self Edge. I wear mine with checkered flannel shirts, canvas chore coats, and fuller fitting jeans. Motorcycle jackets also work here, but can feel a bit costume-y if you don’t in fact ride a motorbike.
- Black Jodhpurs or Chelseas: Nice for a slick, rock-and-roll look. Take inspiration from Andy Warhol, who used to wear them with striped Breton shirts and skinny jeans, or black double riders and sunglasses. One of the upsides to going with a Chelsea here is that they’re a bit more versatile. You can wear them with slim suits for a 1960s throwback Mod look.
- Black Chukkas: A little more conservative the aforementioned options, and thus easier to wear with tailored clothing. Black chukkas can be worn in the winter months with a dark grey Donegal sport coat, white dress shirt, and pair of lighter grey flannel trousers. I also occasionally wear mine with a navy, chunky shawl collar cardigan for a casual, city ensemble.
- Black Slip-Ons: Another great choice for tailored clothing, whether in penny loafer, tassel loafer, or horsebit varieties. If you’re daring, you can try black Belgian shoes (Alan Flusser is reportedly a big fan). Consider black slip-ons with a sport coat any time you would wear a black knit tie. They have the same casual, but refined sensibility.
- Black Derbies: Black derbies can be surprisingly versatile with casualwear. Just get a chunkier pair and you can wear them with an olive or charcoal topcoat, white or black denim, and textured knitwear. One of the guys pictured above is wearing a nice pair of black double monks with a camel topcoat. Black derbies would work just as well here.
- Black Side Zips: One of my favorite styles of casual shoes, but in black, you need the right wardrobe. Think, minimalistic, austere outerwear with slimmer black jeans or grey trousers. Margiela and Lemaire make some nice ones, but you’re paying more for design than build quality (a few of the Margiela ones are made from corrected grain leathers, which is annoying). I mostly wear mine with black or grey leather jackets.