Four Shoes to Own

Shoes take about the same place in my clothing priority as they do on my body: the bottom. Shoes are very important--beyond just no shirt, no shoes--but I prefer other items in my wardrobe like ties, and to a lesser extent suits. So for a gentleman like me, the collecting of shoes is an exercise in efficiency. The goals are (1) always having the right shoes for the day while (2) having as few shoes as possible.

The principles I followed require two brown because shoes always deserve a day of rest between wears to fully recover and one black because brown is the go-to color. To meet that first goal, I add a summer pair, and, in the name of the second goal, I omit a second pair in black at the risk of wearing them on back-to-back days. There is also a balance of formal and causal wear, that fits my professional endeavors and personal proclivities: you may have to make some adjustments depending on your needs. Finally, it is important to remember these constitute the minimum four pairs a gentleman may have to be elegantly dressed. Unfortunately, I own only one of these pair. Nonetheless, here they are.

1. Black Plain Toe Balmorals

These are shoes with closed lacing, meaning the part of the shoe that forms the laces almost closes on itself, with an additional piece of leather sewn beneath to form the tongue. I selected plain toe because this is the only shoe that can be worn with both a dinner jacket and a black suit. The other dinner shoes, pumps with silk bows and velvet slippers, are completely inappropriate for business pursuits and suits; meanwhile, the addition of a toe cap, even a straight tip, renders them too casual for evening dress.

However, if you are the type who will never wear a dinner jacket, you might freely add a toe cap or even some minor broguing with my blessing. And if you wear black tie so often you can afford special shoes, by all means get one of the above or these in patent leather.

2. Cordovan Wing Tips
These are my favorite shoes that I will feature today and will surely be the next pair from this list that I purchase. These are shoes of the country and of Scotland, but the days of men changing their suits upon entering the city and again upon leaving are behind us, so they are perfectly appropriate for any business suit that is not black. As such, they will get the most wear and might as well be the very, very best. Cordovan leather should come from Alden, the Rose Bowl of its cordwaines, and is the most distinctly American aspect a gentleman can add to his business footwear. They are universally distinguished and, despite their immense difference from plain toes, are equally acceptable for all but the most serious of business. While black may be necessary to seal-the-deal, brown is much more stylish and should be your go to. They are also quite dark, adding to their formality.

Gentlemen who are not willing to pay a premium can get the same style in brown, and can go much lighter as well if they are looking to be more casual. But certainly, the 50% premium that cordovans command is well worth it.

3. Brown Penny Loafers

Penny loafers provide support that other types of moccasins do not while still maintaining a casual slip on nature. These will be a gentleman's go-to shoe when a suit is not required, and I prefer a pair that can stand up to some serious walking. Because of the pounding, however, it seems like a pair that a gentleman can save some money on, so I turn to Bass to get welted shoes from America at an affordable price. Alden and Allen-Edmonds are out because theirs are significantly more expensive and drift too far toward driving shoes.

Alternatives include horse bit or preferably tasseled, but I prefer pennies by far. I currently have rubber soled loafers as an even harder-wearing alternative, but this list places elegance above the added rebound of synthetics. A pair of cap toe lace-ups could be in order instead, or in addition for gentlemen whose life demands a great deal of laces. But there's little wrong with wearing these with a suit

4. Boat Shoes

Of course, this shoe must be from Sperry Top-Sider. My AOs are somewhat brighter than this, but they come in a cornucopia of colors. These are for the gentleman to show his whimsical side without going so far as showing his toes. Just as chinos are the gentleman's jeans, Sperry's are the gentleman's sandals. And please, no socks.

If you're not the beach and boat type, the other classic American, casual, summer shoe is the saddle shoe. Get some in white on brown and wear them everywhere from the golf course to the museum. Even further along is the white buck.

With these four shoes, you will have the right pair to look elegant at any occasion that requires a gentleman. If you like shoes, don't stop here. (All images courtesy of the named manufacturer.)

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