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.
Oxfords/Balmorals: Oxfords (British), or balmorals (American) are lace-up dress shoes with closed lacing (the pieces of leather joined by the laces are sewn together at the bottom). Many Oxfords have an additional piece of leather sewn over the toe section, known as a toe cap. If it is missing this piece it is called a plaintoe. Oxfords are your most formal option.
Bluchers/Derbys: These are similar to Oxfords, but have open lacing. They are a little less formal, and are often worn in brown and can have the same embellishments as oxfords.
Wingtip/full brogue: These are characterized by a pointed toe cap with extensions that run along both sides of the toe, ending near the ball of the foot. When viewed from above this style is “W” shaped. A shoe with a wingtip-style toecap but no perforations is known as an “austerity brogue”, and a plain-toe shoe with wingtip-style perforations is a “blind brogue”. Wingtips can be found as sleek, formal balmorals or as chunky casual bluchers.
Semi-brogue of half-brogue: This style has a perforated captoe with a punched medallion in the center. They are most often seen as oxfords.
Quarter-brogue: Just like a semi-brogue but without the medallion on the toe cap.
Longwing: These are like wingtips but with the wing extending all the way around the shoe. Unlike the above styles, they are a predominantly American design. They are almost always seen on bluchers and are commonly made in shell cordovan. Alden is the quintessential longwing producer.
Monkstrap: What, have you been under a rock all these years?
Calfskin: this is exactly what you think it is. Most high-quality shoes are made from calfskin.
Shell Cordovan: this material comes from a horse’s rump and is known for its toughness and durability. Shell also drives a much higher cost than calf. Don’t confuse it with the color cordovan.
Suede: it can be made of any leather but this refers to leather with a napped finish.
“Exotics:” anything outside of the normal materials – croc/gator, ostrich, stingray, and so forth. These are not part of a basic shoe wardrobe.
Last: the shape that the shoe is formed around. Like I said earlier, any respectable shoe company will have products available on a variety of last to cater to a range of foot shapes and styles.
Goodyear Welt: the gold standard for shoe construction – another way to determine if a shoe is of respectable quality. The goodyear welt process is a method of attaching the shoe uppers to the sole and allows for multiple resolings in the shoe’s lifetime.
As always, do your best to match the formality of your shoes to the rest of your dress. Closed laced shoes are more formal the open. Plain toes are more formal than cap toes, which are more formal than brogueing. Sleek lasts are more formal than rounded lasts. Calf is more formal than suede. Leather soles are more formal than rubber.
4. Ebay is your friend.
Although the price of secondhand shoes has gone up in the past year or two (I blame Put This On’s ebay roundups and increased overall demand), the best deals will still be on slightly used pairs. With a bit of knowledge and some patience you can find great shoes with very little wear (often floor models) or shoes that have been lightly worn but are still in great shape. If you’re not already using a saved ebay search to find good deals you should start right now. Aliotsy has a great one here.
Tip: make sure your search also includes stores that carry high-end shoes made by external manufacturers. For example – shoes “made by” Peal & Co. for Brooks Brothers or Ralph Lauren will usually be cheaper than equivalent shoes made by Crockett & Jones, Alfred Sargent, or Edward Green (all of which make shoes for these companies).
5. Make a long-term plan and buy when the price is right.
I generally don’t suggest buying several pairs of shoes at once like I do for shirts and slacks. The high price of good shoes makes buying in bulk cost-prohibitive, so it helps to have an idea of what you need in the long-term; that way you can buy when the right shoe is available at the right price. I could go on about what an ideal business casual shoe collection might look like but I’d probably just be re-hashing Put This On’s 7 Shoe Wardrobe. Read it and embrace it. My day-to-day collection shown above is another great example of a versatile business shoe collection (well, at least I think it is).
6. Take care of your purchases.
This can’t be stressed enough. High-quality shoes that are neglected will not stay pretty for long. Invest in shoe trees and keep them in your shoes whenever they’re off your feet. Use a shoe horn. Maintain your shoes with conditioner and polish (I recommend Allen Edmonds or Saphir). Don’t wear the same pair two days in a row if you can help it.
“Accessible” ($300 and under at MSRP):
Expensive ($300-$800 at MSRP):
Look but don’t touch:
Above, from top to bottom: Peal & Co. Loafers, Allen Edmonds McAllister, Grenson Bert, Sid Mashburn Suede Balmorals, Loake Pimlico. Before you think I dropped 2.2k on shoes – most were bought used and I paid an average of 30% retail costs. Patience is everything in shoe shopping.