How to Choose Better Shoes

In the last ten years, the internet has exploded with innumerable sources for high-end shoes. What used to be a small market of Goodyear welted footwear has become an electronic bazaar with virtual stalls from around the world. In the past, if you wanted a pair of good shoes, you had your pick of two American brands, a handful of Northampton makers, and some Continental labels that were hard to source. Today, dozens of specialized dealers offer MTO options, adjusted lasts, and handwelted shoes made in the Austro-Hungarian tradition.

When shopping for shoes in this environment, it can be easy to get sucked into the endless number of options, especially when you’re scrolling through Instagram accounts and dedicated shoe blogs for inspiration. The photos that catch our eye tend to be of shoes that are sleek, interesting, and creatively designed. So people pause on photos of shapely oxfords in gleaming museum calf leathers, two-toned button boots, and chukkas in jewel tones such as sapphire blue and ruby red. And since footwear blogs tend to be so singularly focused on shoes — the leather types, construction techniques, and historical origins of some style — it’s also easy to find yourself thinking about shoes as standalone objects, disconnected from a wardrobe and be to be collected like Pokémon. I found myself doing this when I first got into fountain pens. The more I learned about filling systems and specialized nibs, the more I wanted certain pens, even though my time would have been better spent practicing my handwriting with the pens I already own.

Such internet-driven shoe shopping doesn’t always lead to good results in a wardrobe. In classic men’s dress, the cynosure of an outfit is typically the triangular area formed by a jacket, shirt, and tie. When done well, this area should lead a viewer’s eye upwards toward the space that deserves the most attention, your face. This is why it can be hard to wear patterned trousers or shoes in unusual colors: they draw the eye downwards. But when shopping online, we tend to be drawn to shoes that catch our eye, which is the opposite of what you want in an outfit. This doesn’t mean you have to get the most boring shoes possible (“They are not cheap; they are also an investment,” Hardy Amies wrote in The Englishman’s Suit. “So design is of the plainest”). Dreadfully boring shoes can sometimes signal a kind of conservatism that suggests you’re too self-conscious and afraid to have a point of view. Instead, get something that complements the rest of your wardrobe and builds towards a style you want to project. Here are three friendly suggestions on how to shop for better shoes.




The overriding theme in this guide is how to create a harmonious outfit, such that no single item stands out on its own. At the most basic level, this means coordinating things according to color, seasonality, and formality. Each item should help complete a scheme or send a message. To stress: this guide only applies to classic men’s dress and specifically outfits that involve a tailored jacket. Casualwear runs on a different rubric.

The best way to start thinking about coordination is through color. Plenty of style sites these days recommend tan footwear as your third or fourth footwear purchase. They’re cheery, bright, and seem like a smart way to diversify a shoe wardrobe that’s already heavy in black and dark brown. Plus, tan is the natural color of spring and summer, and it’s good to have seasonal items in the closet. Supposedly pairing tan shoes with a dark worsted suit is a Southern Italian thing, an old trick that stylish Italian men use to liven up their business uniform. But I’ve never seen anyone in Southern Italy do this, only Americans who fancy themselves to be Italian.

While tan shoes have a place in a larger wardrobe, most men don’t have the kind of wardrobe necessary to support tan shoes. Under a dark worsted suit, tan shoes shine out like a beacon, dragging the eye downward and ruining what should be the focus of the outfit. Depending on the specific shade of the tan, they may not even work with grey trousers and a navy sport coat. Instead, tan shoes should be reserved for brighter and lighter colored outfits. Some examples below of how they’re best worn.



Lighter colored suits: In the photos above, you can see how Niels in Berlin and Yukio Akamine wear tan shoes with lighter colored suits, such as dove grey and tan. Since the entire outfit is light-colored, the shoes don’t stick out. Notably, most men find they only have few occasions to wear lighter colored suits, as suits are typically worn to formal or somber events these days, while brighter, cheery colors are considered more casual.

Lighter colored sport coats: This same trick works with lighter colored sport coats, whether paired with trousers in a lighter or darker color. The jacket’s brightness helps prevent the eye from being dragged down (or, by the same token, the shoes from visually standing out). See how Mark Cho of The Armoury above wears tan loafers with a beige sport coat and mid-grey trousers, Greg Lellouche of No Man Walks Alone pairs tan monk straps with a grey checked sport coat and off-white pants, and Yukio Akamine wears tan shoes with a yellow sport coat and beige trousers.

Similarly bright items: Most of the jackets above are unusually bright, but you can also wear tan shoes with slightly darker colors. In one of the photos above, you can see how Mark pairs tan loafers with a mid-blue sport coat, but his bright white jeans help balance out the shoes. A proper navy jacket here wouldn’t work, nor would mid-grey trousers. Think of this as a brighter version of a navy jacket with khaki chinos and mid-brown shoes. When you brighten everything up one or two shades, the entire outfit has a kind of summery feel that harmonizes with tan footwear.

Casualwear: Again, this guide is mostly focused on classic men’s style and specifically outfits that involve a tailored jacket. It would be too much to try to cover casualwear here, but it’s worth noting that, even in classic men’s dress, tan shoes can go with certain casual ensembles. Tan boots or derbies, for example, can be worn with waxed cotton Barbour jackets or the sort of outerwear you find at Private White VC. Softer, less saturated shades of tan are also very versatile, particularly in the summer.

Men who buy tan shoes typically do it because they want to diversify their wardrobe, but the style only works for wardrobes that are already diversified. Before you buy a pair, ask yourself if you already have a few lighter colored suits or sport coats in the closet, or the right casualwear. If not, stick to mid- and dark browns. They go with everything.




The basic idea above is that you should avoid shoes that visually stick out from an outfit. Tan shoes are the trickiest; unusual colors such as red, green, and blue should be approached with a lot of caution. But even safer colors such as mid-brown or dark brown can have a lot of variation.

There are many subtle things that go into whether a color harmonizes in an outfit, including shade, hue, and saturation. The trickiest, and perhaps least obvious, is temperature, which is about a color’s cast or undertones. Warmer colors have a reddish cast, while cooler colors have hints of blue or green.

The first photo above shows a pair of mid-brown suede Edward Green boots, which are fairly neutral in terms of temperature and thus will be easiest to wear. However, in the two photos below that, you can see how a reddish undertone makes the chukka on the left look warmer. The other chukka has a hint of earthy green, which will coordinate better with the other cool colors that tend to dominate men’s wardrobes — earthy browns, stone grey, and navy blue. You can see this dynamic in this Instagram video by Mark Cho, where he wears toffee suede monk straps with a pair of Nigel Cabourn blue jeans and an ivory linen Liverano sport coat. If his shoes were redder, the combination just wouldn’t work. But in that earthy toffee color, the outfit comes together very nicely.

This distinction can be taken further in the second set of photos. Although these two Edward Green Chelsea boots look similar, the one on the left has just a hint of red underneath that dark brown (it’s the company’s mink suede color). The boot on the right, however, leans cool and thus will be easier to wear (that’s Edward Green’s mocha suede). To be sure, not everything is about temperature. Sometimes things work simply because of a social convention or message. Burgundy shoes with deep red undertones look terrific under navy suits because there’s a convention for that pairing. White bucks, while neutral in terms of temperature, also stand out in an outfit, but they work with preppy ensembles because of tradition. That said, next time you’re shopping for shoes, consider the temperature and whether the color works with your wardrobe.




Someone interviewed me a few years ago and asked if I had any personal style rules. I struggled to think of one. Most rules around men’s dress draw from a time when clothes were bound to ideas about propriety and etiquette, not just aesthetics or personal identity. So we get rules such as “no brown in town” or “no white after Labor Day.” Few people observe those things anymore, let alone know them. I say wear white whenever you feel like it — nobody is going to be offended.

The one rule I follow, however, is about dress shoes. Oxfords are for suits and suits only.

As many readers know, oxfords are a type of dress shoe defined by a closed lacing system, where the facings (i.e., the eyelet tabs) are sewn underneath the vamp. Derbies, on the other hand, have an open lacing system, which means the tabs sit above the vamp. Today, both styles are known as “dress shoes,” which is a technical term for “your fancy shoes.” Oxfords, however, have traditionally been more formal than derbies. Sometime around the turn of the 20th century, oxfords slowly supplanted “high shoes” and boots in most men’s wardrobes (some at the time even fastened with buttons). Before that, formal dress shoes often looked like balmoral boots or button boots, before they eventually transitioned into what we today would call oxfords. Before World War I, such oxfords were called “low shoes,” partly to distinguish them from the more common boot. See this guy below, who got married in boots.



You can see the similarities. Formal shoes at the time had very clean, sleek lines, often uninterrupted. Oxfords (or “low shoes”) were in keeping with that tradition, which is what made them suitable for the sort of formal business suits men would wear into London (or, before that, with frock coats).

Derbies were also worn with suits, but they were more common with relatively more casual suits — a tan gabardine wool suit, a suit with a bolder pattern, or a suit that would typically be worn out in the countryside. They were also worn with sporting clothes, such as sport coats. With something like a plain navy, worsted three-piece, you’d more likely find men wearing something like a simple, black, plain toe oxford. With a chunky herringbone tweed suit or sport coat, it might be a brown suede derby.

Few people know these conventions today, but they understand them intuitively. When shopping for shoes, many men are drawn to oxfords because they look sleeker and dressier, and many equate dressing up with dressing well. But oxfords only really work with suits, and most men, even those who are clothes mad, don’t wear suits often enough to justify having more than one pair of oxfords. Instead, they live in jeans, chinos, or sport coat and odd trouser combinations, all of which call for more casual shoes.

This doesn’t mean that suits can only be worn with oxfords. There’s a rich tradition of men pairing more casual shoes with their city suits, including everything from Chelsea boots to tassel loafers to Norwegian split-toes. It’s only to say that oxfords should be worn with suits. The bigger the gap between the formality of the shoes and the trousers, the more discordant the outfit. Perhaps worst of all is seeing fine leather oxfords being worn with blue jeans. 

To be sure, some men get away with wearing oxfords with sport coats, perhaps because their oxfords are a slightly more casual variant, such as brown suede semi-brogues, or perhaps because their tailoring is exceptional. Bruce Boyer often wears suede punch-cap oxfords with sport coats and he’s one of the best-dressed men I know. But most people would look better if they just stuck to the rule. Instead of buying shoes as though you’re checking off a list of menswear essentials — black oxfords, brown loafers, brown derbies, etc. — consider what works for your lifestyle, wardrobe, and needs. If you wear suits only once or twice a year, you’d be fine in a pair of brown derbies, which can double as your daily shoes if you’re mostly in sport coats. Oxfords, on the other hand, should only be worn with suits.