There is some confusion among men today as to which shoes are really necessary in a well-dressed man’s wardrobe. Here we bring you classic shoe models for men that have been around for generations.
Below we showcase a complete men’s shoe collection from the iconic fashion magazine Esquire Apparel Arts – a magazine that had its heyday in the 1930s.
The shoes are from top to bottom, left to right:

- Patent leather opera pumps
- Brown calf monk front shoes for spectator sports wear
- Reversed calf shoes on a town last for spectator sports, country, or very informal town use
- Brown calf Norwegian brogues for country and spectator sports
- Black calf town shoes with undecorated toe cap
- Brown wing tipped brogues with overhanging tongues for golf or country wear
- Brown calf town shoes on the new square lasts with perforated toe caps
- Black calf shoes with cloth button tops for formal and semiformal day wear
- Patent leather evening oxfords
- Buckskin house slippers
- On the floor Norwegian peasant shoes for lounge wear at club, home or resort
- Brown calf field boots for country and park riding.
Classic shoe models for men
There are hardly many of us who can match this range of shoes in our wardrobes. While many certainly have a large number of shoes at home, we often end up running into a bit of the same type of shoe styles within which we have our favourites.
Without claiming to be a complete guide to different shoe styles, here we take a look at some classic shoe styles for the gentleman based on those mentioned above.
1. Opera pumps

Here is a pair of classic opera pumps in patent from venerable English company Bowhill & Elliott, founded in 1874, The shoes are handmade in Norwich, England. This shoe model dates back to the Victorian era and is the most formal shoe for tuxedos – something that few think about when choosing a shoe model for this festive outfit nowadays.
2. Monk shoes
Here’s a pair of monk shoes from Loake 1880, handmade in their factory in Northampton, England with calfskin uppers and welted leather soles.
3. Suede Brogues
A pair of suede brogues from Loake 1880 and the British shoe manufacturer’s premium collection where the production time for a pair of shoes is 8 weeks.
4. Derbies
Derbys from British Edward Green, which are handmade from calfskin with a welted leather sole. They provide a durable construction and extend the life of the shoe. This model is very similar to the shoe model called “Norwegian Brogues”.
5. Black oxfords
Black calfskin oxfords are one of the more versatile models among shoes. Here a pair from Crocket & Jones.
6. Golf shoes

As golf fashion has evolved to focus on more functional garments, it has also become increasingly difficult to find old-fashioned golf shoes. In the past, a common model was Brogues with a well-fitted “tongue” with fringes. An exception to this is the Italian company Nebuloni, which still produces high-quality golf shoes in the old-fashioned design.
7. Brogues in brown leather
Here we have the ultimate shoes for winter use from Crocket & Jones. Brogues that are made from “Country Grain Leather”, the finest quality calfskin that is coarsely embossed. Here a Wing Tip model, unlike the picture pictured at the top.
8. Button Boots

It is extremely rare to find this type of damask-looking “Button Boots” on the market at the moment. Italian Enzo Bonafé has some really nice models in its range though – something we noted earlier in the inspiration post about the Orient Express.
9. Oxfords for evening wear
In the 1930s, when style rules were still stricter, more stylish oxfords were common for evening wear. Here are extremely stylish oxfords from Crockett & Jones, which can be seen being worn by James Bond in the film Skyfall. We can also recommend the Parliament model from Loake 1880 and their Export Grade line for those looking for stylish oxfords of the highest quality.
10. Indoor leather slippers
Here we have a pair of handmade slippers in embossed reindeer leather for indoor use. Something for the nostalgic! You can also find these in slip-in style.
11. Penny Loafers
Classic penny loafers from Norwegian Aurlands. The original model was made back in 1926 by founder Nils G. Tveranger and is still a favourite today thanks to its timeless design and high quality.
12. Boots
As horse riding has become increasingly rare as a leisure activity for men, distinctive riding shoes with high shafts have also declined in number. Instead, we now see more and more Chelsea Boots and jumping boots in use, both for riding and for everyday wear. Here’s a pair of welted leather Chelsea Boots from R.M.Williams, made from a single piece of leather.