3 pairs
1) Brown balmoral oxford with straight captoe. No brogueing. This will function as the cornerstone of your shoe wardrobe. Same functionality as a conventional brown gooseneck captoe oxford, but I have always found balmoral oxfords particularly elegant. And it'll be a different design compared to the conventional black captoe oxford.
2) Black captoe oxford. Well, most Singaporean men still find that they want a pair a black shoes. Nothing wrong with that.
3) Adelaide oxford. Brogued. Brown. Just to add variety to the collection. Adelaides are a very balanced design imo.
If extended to 5-8 pairs
4) A "dress" chukka. Dark brown. 3 eyelets. Sleek last. Topied sole. Incredibly versatile. To wear with jeans, on travels (because you can wear it with casual and formal wear, reducing number of shoes to pack). And the topy allows you to wear it in rain and mildly wet weather.
5) A dress derby. Also dark brown. Smooth calf. 2 or 3 eyelets. Single leather sole. For days that you want a formal pair of shoes but oxfords bore you.
6) Brown double monks. Just for variety and for days you are just too irritated for laces.
7) Loafers in brown suede or calf. I prefer penny or string. Tassel loafers might be a little "dandy" for some. Just for dress down days, shorts, jeans.
8) A chunky ba***rd. Brown suede or grained calf, dainite soles, derby, semi or full brogue. For bad weather dress down days.
