Thundermarch and others, read and re-read all of your responses, got it, thanks for the really useful advice.
Almost the same question but this time for a dress down office where jeans, cotton trousers, fleece and polo shirts are standard. What would you recommend us to buy to start our shoe collection for this environment?;
- just 3 pairs
- 5-8 pairs
Intrigued ..............
I think my choices would be quite different for this list:
3 pairs:
1) Suede chukka
- mid to darker brown, rubber soles, round toed
- Again, because of the incredible versatility, this should be the first pair
- goes with blue denim, grey denim, khaki, cotton chinos, casual linen trousers, and if you were willing to take a risk, you could even wear it with a lighter coloured, casual suiting
2) Suede or textured (embossed) calf loafers
- scotch grain / pin grain
- this pair can be lighter if you already have a darker coloured pair of loafers
- take your pick, tassel / penny / round / wholecut
- again, goes with many things, and in addition, they also go with shorts, and arguably, the only footwear you can wear sockless without looking like a fool
3) A casual / clean derby
- either a simple 3 eyelet derby or even a wholecut 4/5 eyelet derby
- plain toe
- rounded last
- suede or textured calf
- especially great with jeans
Extended to 8 pairs
4) A full brogue wingtip oxford
- either in smooth calf or something subtly textured
- round toed, mid to dark brown
- I haven't mentioned this in my earlier list but the full brogue is really versatile too.
- I think an oxford gives a smart edge to an otherwise casual outfit, and a full brogue complements it, and otherwise keeps the outfit congruent
5) A jumper boot
- If you can accept the idea of wearing a boot in SG, then you'll love how they look with jeans or chinos
- If you don't like the jumper boot style, you can consider a Galway-esque type design and use to opportunity to play with two toned leathers
- rubber soles
6) A split toe derby
- a lot of guys like this model
- casual, easy on the eyes, a million permutations possible
- goes with almost everything from jeans to standard office attire
7) A suede double monk
- many people might not agree, but amongst all the derbies and loafers and chukkas, this just adds a bit more variety and is easier to put on than a lace-up. And easy to put on is one key requirement for casual attire
8) A lazyman
- The most popular designs would be a full brogue of some sort
- again, this is for variety, and for ease-ness of putting on