Alfred Sargent


Business Casual Basics, Part III: Shoes

Previously: Part I, Part II. This is the third installment for my fellow white collar ballers.

If you’ve spent any time learning about men’s clothing (be it from family, friends, or the internet) you’ve probably heard a disproportional amount of talk about shoes. Shoes are a huge part of what dressing well is about (both in cost and importance), even though they take up a fairly small amount of space on your body. It can’t be stressed enough; shoes are often what separate the men from the boys, and business casual workplaces are notorious for bad shoe choices. A little bit of knowledge here will go a long way. Shoes are also the foundation of your outfit in stylistic and structural terms; if you buy well and take care of your purchases they will in turn keep you comfortable and stylish for decades.

1. Save up some money.

This one has the potential to get expensive. Accept the fact that high-quality shoes will be expensive if bought new, and can even be pricey when bought secondhand. Thrifting can be a good option here as well.

2. Learn the differences between “real shoes” and bad shoes.

High-quality shoes are expensive for many reasons, but the biggest two are material quality and construction. These qualities are much more important with shoes than they are in a shirt or pair of pants because shoes need to stand up to a tremendous amount of wear. Read Kiyoshi’s post and Put This On’s article to get a sense for what I’m talking about. If you buy a high-quality welted shoe that fits well and is well taken care of it will last for decades. Trust me.

Need some help finding out which brands can be trusted for high quality shoes and which can’t? I’ve included a short list at the bottom of this post, but my rule of thumb (toe?) is this: don’t buy shoes from any manufacturer that can’t tell you what last their shoes are made on. Any respectable shoe maker will have products on a range of last choices and will be able to tell you about them.

3. Understand the different styles and their applications.

Ready for some shoe terminology? This should be enough to get you started.

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The In-Between Wardrobe, Part II: Shoes

The “In-Between Wardrobe” is a series of articles aimed at helping men find items that will play a versatile role in their closet. It is written with the idea that most men don’t wear extremely formal or casual clothing on a regular basis; they usually need items that are somewhere in the middle. See all articles in the series here.

Shoes are a critical element of in-between dressing, and are one area that is constantly being messed up by men that don’t know any better. The core idea behind finding an in-between shoe is balancing casual and formal features to achieve something that can be worn with a large variety of clothes. 

First, it is important to understand what makes a shoe a “good” shoe and how to look for high-quality materials and construction in footwear. If you’re not familiar with these concepts, read my previous post on that topic. Once you’re on board with that, join in below.

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A Summertime Favorite: Penny Loafers

Once the weather warms up and the days get long, I often find that the best shoes are either sneakers or slip-ons. I typically wear sneakers with jeans and casual outerwear, and slip-ons with dressier trousers and sport coats. Styles can really range, but most of the time, sneakers tend to be white and minimalistic, and the slip-ons tend to be penny loafers.

The penny loafer is often thought of as a quintessentially American shoe — a style that’s most at home with tweed jackets and Shetland sweaters, as they were originally worn on Ivy League campuses in the mid-20th century. Today, however, you can safely wear them without any preppy connotations (although, you can also wear them as such, if you wish). With a sleeker pair of European pennies, for example, you can combine them with a soft-shouldered sport coat, wool trousers, and an open collared shirt for a very dégagé Continental look. With some beefroll loafers, jeans, and a light jacket, you can go back to looking like an American, but in a way that doesn’t feel too preppy. 

If you haven’t yet got yourself a pair, consider some of these:

  • Highly expensive at $750+: JM Weston’s 180 moccasin and John Lobb’s Lopez are pretty iconic, with the first having uniquely high walls around the toe that help distinguish it from the pack. My favorite loafers in this price tier, however, are all from Edward Green – an English firm known for its tasteful designs, quality construction, and beautiful finishing. Check out the Piccadilly, Montpellier, Sandown, and Harrow to start.
  • Pricey options between $350 and $500: Less expensive, but no less well-made, are loafers from all of your usual suspects. Carmina, for example, has something that looks very much like Edward Green’s Montpellier, while Alden has a wide range of handsome American designs. More recently, Wildsmith (a bespoke shoemaker once famous for their unlined loafers) relaunched as a ready-to-wear brand, and although their loafers aren’t as close to their originals as Edward Green’s Harrow, they’re priced competitively. Shipton & Heneage will also have a nice range of options, and they’re made a bit more affordable through the company’s Discount Club. Additionally, Crockett & Jones is very much worth a look, as are Alfred Sargent, Sid Mashburn’s house line, Kent Wang’s antique calf loafers, and the newly launched Paul Evans.
  • A bit more affordable at $350 and below: Of course, for more affordable shoes, there’s always Allen Edmonds’ factory second store, where the company heavily discounts shoes that didn’t pass quality control. Flaws are often very, very minor, if even visible at all. Loake’s 1880 line is also worth a look, and they sometimes produce for Charles Tyrwhitt and Herring (just note that some Loake-made shoes aren’t of terribly good quality, so use good judgment). Similarly, Ralph Lauren and Brooks Brothers will have some nice models, even though their quality can really range. Stick to the stuff that retails for $350 and above, and wait for end-of-season sales. In addition, Meermin offers some of the best price-to-value ratio right now in footwear, especially once you take into consideration their made-to-order program, and Jack Erwin is the best I’ve seen in the sub-$200 price range. For more American styled loafers, check out Rancourt and Bass’ Made in Maine collection.
  • Shell cordovan: Lastly, shell cordovan loafers are worth highlighting. Although shell cordovan is traditionally a workboot material, it works wonderfully today for slightly dressier styles (think wingtips, tassel loafers, and penny loafers). Alden’s Leisure Handsewn is a really beautiful American model, while Carmina will be more European. Meermin may also be able to make you something through their made-to-order program.

(Pictured above: Hooman Majd in his fifteen year old Edward Greens)