If you’re like me you haven’t spent much time on clothes. When I look around the office most guys don’t dress very well. Now that business casual and casual fridays are so prevalent, style for men has taken a step backwards.
I started in 2012 with the goal of upgrading my clothes and appearance. This is a huge change for me, so I decided to learn as much as possible and build up a new wardrobe slowly.
The two largest expenses are suits and shoes. I opted to start with shoes, as most men don’t wear a lot of suits anymore – unless you’re a lawyer or banker. I have not purchased a suit since starting this campaign. I will talk about it when I finally replace or supplement the two I have that get brought out at weddings and funerals.
DRESS SHOES
Everyone should have a pair of black and brown dress shoes. A good pair of leather shoes can set you back $200-$300, or more. The good news is that with proper care these can last you a lifetime. The style won’t change. All you need to do is have them re-soled for about $75. If you don’t have the money to buy one pair of expensive shoes, let alone two, you can search ebay. If you buy quality shoes from a good seller you shouldn’t have any trouble – just spray some disinfectant in them when they arrive. You can get a great pair for around $50 if you watch the auctions closely.
Know your size if buying online. Here is a link to measure this SHOE SIZE.
1. Oxfords – these are divided up into two subcategories; Balmorals and Bluchers.
Balmorals – These are more conservative and have less decorations on them. They feature closed lacing. Wear these with suits and formal wear. 
Bluchers – These can have more decorations on them like brogueing (the holes) and feature lacing on the outside. These are versatile and can be worn with suits, blazers and even jeans.
2. Slip-Ons – As the name implies, these shoes do not have laces. These are used for casual dress with blazers and dress pants, but can be worn with jeans.
3. Monk Strap – A casual dress shoe with a strap across the instep. Available in a single or double strap.
4. Saddle Shoes – This shoe is similar to an Oxford-type shoe, but having a band of leather in a contrasting color across the instep.
5. Boat Shoes – a moccasin-like shoe with a rubber sole that was originally designed for good traction on a boat deck. These have since been used by men as a casual summer shoe. They can be used with casual pants, like chinos, shorts, jeans or swimwear. Boat shoes are frequently worn without socks. If you choose to wear socks, you can use low-cut loafer socks.
6. Dress Boots – similar to a dress shoe, but with a taller profile. They are used mainly in the fall/winter, but can be worn year-round. They are versatile and can be worn with business casual wear or jeans.
7. Desert or Chukka Boots – These are usually made of leather or suede in the colors of brown, tan, or grey, but other colors are available. If you have dress boots you probably will not need these. If you’re on a budget, a pair of chukkas will usually be cheaper than a pair of dress boots.
8. Canvas Shoes – a classic style of shoe great for casual wear, especially in the spring and summer seasons. White is the most common color, but beige grey, and black are also seen a lot. If you wear your running shoes a lot when wearing jeans, try switching to something like these.
9. Running/Athletic Shoes – save these for the gym or for your run. Invest in a good pair, by doing some research on reviews. An even better approach is to find a store near you that will analyze your feet while you run and recommend a pair based on your foot shape and the way you move.
10. Sandals/Flip-flops, Crocs – summer-wear shoes that don’t require socks.
11. Work Boots, Hiking Boots, Cowboy Boots – more of a specialty footwear, but can be worn with casual wear.
SUMMARY – When building or analyzing your wardrobe pay particular attention to your shoes. People notice these more than you think. Start with a budget to add the basics (see below) and then gradually replace these with quality shoes that can last a lifetime with proper care.
BASICS
a. Black Balmoral
b. Brown Blucher
c. Brown Chukka or Dress Boot
d. White Canvas Shoe