Reader Question – Which First Three Pairs of Shoes to Buy

I’ve been meaning to write specific articles answering readers questions for some time now. I receive them frequently and I’m sure that if one reader has a question, it’s probably applicable to at least a handful of others who make up the thousands of weekly readers of Timeless Man.

A recent message from a reader has prompted me to finally start properly addressing some of these questions more formally and in depth i.e. specific articles dedicated to certain questions.

Below is a recent question from Jian, which I felt was particularly relevant, as it’s something which I’m sure a lot of other men try to work out, particularly in the early days of building a quality wardrobe.

“As someone who’s starting out in the classic menswear world, and living in Australia, (Melbourne, in particular, where our winter isn’t as chilly as the European winter), what do you think would be the 3 best pair of shoes to start with, considering I already own a brown cap-toe oxford and a cordovan shell tassel loafer
I was thinking of acquiring a pair of suede chocolate tassels, and two more others.”

The essence of the question is about versatility. If you only own three pairs of shoes and need to make them work across the spectrum of situations you’ll find yourself in on a weekly basis, which three pairs will allow the greatest amount of flexibility to work across common situations.

If you’re on a budget, then this article on the best value entry level quality shoes will help.

The first consideration has to be of your personal circumstances. Do you work in a highly formal environment and attend a high number of formal after work events? In which case you need to err on the side of more formal, polished and darker footwear for, say, two of the three pairs. If you’re in a creative field where the dress rules are relaxed and you only need formal shoes for the occasional wedding, then two pairs which are more casual and a third which can straddle formal and less formal situations is the direction you need to head in.

My bespoke Cleverley’s
Some of Corthay’s more adventurous styles

The advice outlined below is designed to cover both ends of the spectrum (formal and casual) and something in between, along with some additional suggestions for each option, which can add or remove formality, depending on your personal circumstances. They are in no specific order, as your lifestyle will dictate which you should acquire first. They’re also influenced, in part, by my personal preferences and I’ll point out why, when it’s relevant.

The three major things to consider with any clothing acquisition aside from the shape itself are colour, texture and pattern (I really need to write an article on pattern). Darker colours with smooth surfaces and no patterns are the most formal, and become less formal as the colours lighten, surfaces gain texture and complexity of patterns increase. These factors should influence your purchasing decisions in terms of how they apply to your lifestyle.

Black Tassel Loafers: (personal preference alert number one). I’ll be crucified by some of the old hands of menswear for this, but you do not need black lace-ups among your first few pairs of shoes unless you work in a highly formal environment and you’re likely to be cut off at the knees for wearing anything other than polished black lace-up oxfords. A polished pair of black lace-up oxfords only work in formal situations and they struggle eternally to make the cross-over to even semi-formal environments. Black tassel loafers work in all but the fussiest of workplaces (particularly when polished and worn with a good suit), they go particularly well with stone-washed denim, they work with regular denim (as long as the denim isn’t very dark), look good with creme suits or chino’s, as well as white chino’s. You can also wear them to weddings, funerals and black tie.

Black tassels at a recent fitting with P. Johnson. Worn with Ambrosi trousers and Simon Crompton’s crew neck merino sweater

If you want something in between, go for black cap-toe oxfords with some brogueing on the cap, heel and throat. It takes away an element for formality, but they still can’t cross-over beyond formal. If tassels aren’t your thing, penny loafers will do the job. I happen to love tassel loafers, but I appreciate that some don’t.

Brown suede loafers: (this may have accidentally descended into an article on why you should buy tassel loafers at every opportunity). Assuming your black loafers can straddle formal and informal situations, brown suede loafers are heavily geared towards casual environments, but can also work in the office, depending on how formal you need to be. Brown suede is the chameleon of the shoe world and can be used in so many situations (see this article for why you need more brown suede in your life). Sure, it can’t be worn formally, but it’s totally at home in semi-formal environments i.e. with grey, navy, creme or brown flannel (or navy and grey worsted suiting), any shade of denim, white chino’s or creme anything. If loafers aren’t your preference, cap-toe oxfords or adelaide’s are a good alternative.

Barbanera’s (and Sweep). Worn with Blackhorse Lane denim.

Brown adelaide’s or oxfords: Jian, this isn’t as relevant for you as you already own cap-toe oxfords, but I’ll come back to another option after this. For me, cap-toe adelaide’s are among my favourite shoes (see my Saint Crispin’s, pictured below). In dark brown, they’re brilliant with just about any suit (other than black, obviously) and they also look great just with separate trousers and a shirt. If you want to err towards the more casual side, something in pebble grain, alligator or a rougher animal skin will lend itself more to jeans. The compromise with lace-ups is that you lose the ability to wear them without socks. Part of the reason loafers are so great is that they look good both with and without socks, whereas lace-ups look ridiculous without socks. Jian, if it were me, given you already have brown oxfords, I’d probably go with lace-up dark brown suede oxfords/adelaide’s for one of your next pairs.

Saint Crispin’s (made to measure)

Creme denim, brown suede

So, to summarise, if I only owned three pairs of shoes, they’d be black calf tassel loafers, dark brown suede tassel loafers and either brown suede adelaide’s or the same but in calf. If you’re super formal, swap out the black calf tassels for black oxfords and if you’re super casual, maybe swap out one pair for some misserocchi’s or similar (I live in these in summer) and they’re brilliant with slim fitting chino’s or denim, as well as lightweight suiting, no socks and an open collared shirt.


Hope that helps.

For anyone else, feel free to email me at the usual address ( and I’ll try to answer any specific questions you have, with a view to doing more reader questions articles in the future. Or just leave a comment below.

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  1. says: AN

    Great article Andrew. I’ve read it several times and it’s helped me plan the next shoe purchase (and there’s always a next shoe).

    Would love to see similar articles for first suits (beyond the navy and grey article), and first sport coats. Would be helpful for the guy starting out in the workforce, and also the guy looking to rebuild a wardrobe e.g. going full bespoke.

  2. says: KG

    Thanks Andrew, this is a great blog – totally came across it by chance but will be making this a regular going forwards!

    I liked the idea of black tassel loafers; I have a couple of grey trousers that I feel brown just doesn’t quite feel right with. I was thinking the casual nature of the shoe will off-set the formality black brings to an outfit. I struggle with picking the right shoes when I decide to wear a black shirt/polo – it’s either sneakers or a pair of black full brogues; neither of which are ideal I feel!

    I work in banking so the Mon-Thu is usually a suit and we get dress down Fridays where I can break out the blazers and trousers (and brown shoes). [pre covid anyway]!

    What would your recommendation be for the next pair given I have the following:

    – black calf captoe oxfords and black calf full brogues – worn for work with suits (navys/greys)
    – dark brown calf double monk
    – dark brown calf tassel loafers (C&J Cavendish)
    – tobbaco suede penny loafers

    PS to your other post about Loake 1880 – I own a couple of them and agree with you to save up for the C&Js as the quality is night and day.

    1. says: Andrew Doyle

      Thanks Krish. Glad you like what you’ve found here.
      I live in tassel loafers these days (wearing brown suede tassels as I write this) and rarely wear lace-ups anymore.
      I’d rarely wear loafers with a polo, as polo’s are so informal, but if you’re wearing lace-ups, maybe aim for suede. Black suede is nice. It’s not often chosen but is underappreciated in my opinion. Brown suede is safer but I don’t like it with black shirts.

      For your next pair (if you like wearing black shirts), I’d be going for black calf tassel loafers. And, if you can, go with braided tassels. The braids make them work better with the texture of less formal trousers (jeans, chino’s) but the calf makes them dressy enough for suits and you won’t notice the braids so much. I love my C&J Langham 2’s (slightly more elegant last than the Cavendish and they have braided tassels, as opposed to the Cavendish’ non-braided tassel). They’re brilliant with jeans and a polo, but equally at home with a navy or grey suit and nice socks. I plan to make it my life’s work to have James at C&J produce more RTW Langham 2’s, over Cavendish, but I have my work cut out for me.

      I’d also recommend checking out Alexander Kraft’s Instagram feed for loafer inspiration. I struggle to read his posts, but can’t argue that he wears loafers across formal and casual better than just about anyone else.

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