1. The Brown Brogue
The brown brogue will quickly become a staple in any man’s wardrobe. It’s as versatile as it is stylish. Ready for this? The term “brogue” is derived from bro, the Gaelic word for shoe. Brogues are characterized by the unique punching or decorative perforations along the shoe’s leather uppers.
Did you know that brogues were originally added to leather shoes to serve as drains for muddy water?
I recommend a semi or quarter-brogue in a dark brown for your first pair. If you’re feeling sartorially inclined, go for a full-brogue (wingtip) in a tan/cognac shade. Keep in mind a pair like this is sure to turn heads, so if you’re not that comfortable with the attention, stick with a darker brown with minimal broguing. This will ease you into the wonderful world of brogues and give you limitless options to pair with jeans, chinos or wool trousers.
2. The Suede Chukka
Surprised it’s number two on the list? There’s a good reason why.
Though not as dressy as brogues in the formality spectrum, it does land above the sneaker. It’s been said that the chukka boot is the first dress-casual shoe, which allows for tremendous versatility. Chukkas can play nicely with a suit, and can easily be worn casual with dark wash denim and a white t-shirt.
The chukka is a simple shoe with open lacing and two or three pairs of eyelets. You’ll typically find this ankle-high boot in suede or leather.
Did you know that a form of chukka, popularized as the desert boot, has its origins in the British military? Because of its comfortability and durability in harsh desert conditions, chukkas became many soldiers’ leisurewear of choice.
3. The Brown Loafer
Casual, comfortable, cool. Dress them up, dress them down. Loafers are your summer go-to. Heck who says you can’t wear them year round?
Though not recommended to wear with a full on suit, loafers look great paired with a sports coat and denim or chinos.
Did you know that tassel loafers originate from the same design found today in boat shoes?
Less formal than lace-ups, the loafer comes in a myriad of colors of black, navy, and even green or red for the bold. I suggest a brown pair for maximum versatility. Leather or suede, it’s up to you.
4. The Canvas Sneaker
Sometimes even the most dapper of men like to go casual. And with the casual aesthetic popular as ever, it’s good to have a go-to casual footwear option. The canvas sneaker is great for all types of casual outings from ballgames to backyard BBQs.
I suggest going for a pair in a neutral shade of beige, white or gray. That way you won’t have to think too much about what to wear them with.
5: The Oxford or Derby
A black Oxford or Derby is typically the first formal pair of shoes a guy owns. I know mine was. But it was of the square-toed variety which I do not suggest. I recommend a more classic rounded toe Oxford or Derby.
You may be wondering what’s the difference between the two. In short, Oxfords have closed lacing whereas Derbys have open lacing. As for which is more formal—the Oxford.
Did you know that the Oxford is named after Oxford University in the UK? Before this, the Oxford has its origins in Scotland and Ireland, also known as Balmorals.
I recommend a quality pair of Oxfords. The two main factors that comprise a quality shoe are price and make.
6. The Brown Leather Boot
A brown pair of leather boots makes the cut, and for good reason.
Depending on the style, you can easily add a bit of sartorial sophistication or rebellious ruggedness to your look. You’ve got dress boots, casual work boots, chukkas, chelsea boots, and even cowboy boots.
You can opt for a more casual work boot or stylish dress boot depending on whichever your preference is. Whatever the case, there’s a certain character about a well-worn pair of boots. Some guys go as far as to intentionally beat the hell out of their boots just for that much desired worn in look.