For those of you who are just getting into dress shoes a question that you may ask yourself is ‘What do I need to make a well-rounded wardrobe?’ And it is a valid question too as there are a lot of options out there and knowing exactly what to get can be quite daunting, like when I have to pick a cloth for a MTM suit. The more options and availability the harder it can be to actually lock down a choice. So, allow me to let you know what you actually need for each amount of shoes one could possibly have.
For the sake of argument, let’s say that you have to wear dress trousers and a jacket each day. It doesn’t have to be a suit but has to be dressy.
So, if you could only have:
1 pair, then what would it be?
- This will be greatly debated but in the modern day of dress and not having to wear a suit each day, I am going to say that the shoe that can take you the most places from semi dress casual to a formal event is a black wholecut oxford. The reason being is that it can go with nearly any dress attire, can be dressed down as well but more importantly can allow you to not have to buy a new pair of shoes solely for the occasion of needing to attend a black-tie event. That means, it is pretty much the one shoe that can take you through every scenario possible when having to dress smart.
2 pairs, then what would it be?
- 1. The Black Wholecut
- 2. The Brown Brogue. For me, never having to attend a black tie event make the brown brogue the most versatile shoe there is. One could in theory argue that a burgundy brogue could be more versatile but as more people are prone to wearing brown I will stick with that as it can nearly go with everything
3 pairs, then what would it be?
- 1. The Black Wholecut
- 2. The Brown Brogue
- 3. The Brown Suede Loafer. For nearly every outfit that is not a suit, the brown suede loafer will be your best friend. It looks good with nearly everything and is just so easy to want to put on….with everything!
4 pairs, then what would it be?
- 1. The Black Wholecut
- 2. The Brown Brogue
- 3. The Brown Suede Loafer.
- 4. The Apron Toe Derby (does not have to be a split toe). This can be in any color but black and can be in either leather or suede. It is a shoe that simply adds another element to your wardrobe and goes well with separate piece outfits (think non-matching trousers and jackets).
5 pairs, then what would it be?
- 1. The Black Wholecut
- 2. The Brown Brogue
- 3. The Brown Suede Loafer.
- 4. The Apron Toe Derby
- 5. The Smart Chukka boot. While a chukka boot can be seen as more casual if you get on that is on the dressier side (i.e. thinner soles) it can be one of the most versatile pieces of footwear that you have, like your brown suede loafer. A snuff suede version is my personal favorite but this is not a concrete rule for color.
After 5 pairs you can really just start going crazy and it will most certainly depend on the type of climate that you live in. I personally love loafers and boots, mainly because I am getting lazier as I age and like to be able to slip on and off my shoes, not to mention the amount of traveling that I do nowadays. But if you are confused about your first 5 pairs, stick to this guide and you will have all of your basis covered and a good range of diversity for nearly any outfit you can conjure up!
Happy Shopping!
Justin, ‘The Shoe Snob’
Been enjoying your blog for some time now, and appreciate your thoughts on show design, construction, quality and the state of the current shoe world. Wonder if we could fit a good set of dark blue Oxfords on the equation (range 5 to ten pairs perhaps?). They seem to be relatively off the beaten path yet work well with all manner of grey, blue and black suits.
Kind regards,
Just got rid of a gorgeous pair of dark brown suede George Cleverly loafers, similar to your photo above. The last was elongated (like Cleverly is known for) and seemed to dressy for the mid-west. I like the rounded toe last of Alden and Ralph Lauren marlow loafers in shell cordovan, somewhat casual and versatile. I also own the Ralph Lauren marlow shell wingtip, similar to the brogue you recommend. I always enjoy reading your blog and have enjoyed reading your personal stories too. Keep up the great work!
Just got rid of a gorgeous pair of dark brown suede George Cleverly loafers, similar to your photo above. The last was elongated (like Cleverly is known for) and seemed to dressy for the mid-west. I like the rounded toe last of Alden and Ralph Lauren marlow loafers in shell cordovan, somewhat casual and versatile. I also own the Ralph Lauren marlow shell wingtip, similar to the brogue you recommend. I always enjoy reading your blog and have enjoyed reading your personal stories too. Keep up the great work! Hope to someday own a pair of Stefano Bremer.
Great article. Keep it up
Hahahaha black wholecut oxford shouldn’t be in top ten. Hell maybe not even in top twenty. (Which for most normies means – should never be bought). Let alone 1st shoes you buy.
Its formal. Funeral formal. Strict and boring. It creases and looks like cheap crap after half-a-dozen wears and as a general rule a wholecut oxford would be more expensive (rightly so as its harder to make), it will also usually come on a leather sole (which means you can’t go outside in it for the fear of: rain, stones, tarmac, mud, dirt or anything else).
The rest of the list is… generic. Brown brogues, some derbies, those ugly chukkas that won’t become the fashion despite all of the attempts at selling them as such.
I have to agree regarding black wholecut oxford. A black cap toe oxford would be much better for office wear and only couldn’t be used for black tie (although in a pinch most people probably wouldn’t care as long as you get them nice and shiny). I’m 41, and the only times I’ve needed to wear black tie were being in someone’s wedding party where I was wearing rental anyway. If you happen to be in the 1% of population who gets invites to other black tie events regularly, you likely have way more than 5 pairs of shoes, and might want patent leather as well for your black tie outfit.