The Oxford Shoe Trinity: The Only Three You’ll Ever Need

The only three you’ll ever need

While having a conversation recently, I was approached by a young man asking advice on choosing a few pairs of dress shoes that I thought could anchor a wardrobe throughout his career. Reiterating my belief on investing in quality first, I proceeded to give him a roadmap on which shoes I thought would last him a lifetime.

Defined by their closed lacing, the term oxford shoe covers a wide range of different styles. No matter which pair you gravitate towards owning, assembling a range of oxford shoes enables you to easily dress for the situation, whether it be casual or formal. I narrowed down my list to a trinity. With just 3 shoes, you’ll have options and a great foundation from which you can build upon your wardrobe further. 

1. Black Cap Toe

creative formal attire

 It wouldn’t be a legitimate list if I didn’t put a pair of black shoes. The most formal shoe on this list, the classic black cap toe, is easily the first shoe every man should own. I wear these shoes everywhere…work, weddings, even a night on the town. They’re a workhorse when it comes to dressing formally. The great thing about well-made oxford shoes is that their style is eternal.

You’ll never have to buy another pair of black shoes if you care for them correctly. Even second-hand shoes are fantastic. I’ve been wearing a pair of Allen Edmonds Park Avenues that I purchased from eBay 10 years ago. I’ve learned to take care of them, polish them and get them resoled when they need it. A true must-have in any trinity.

2. Medium Brown Wingtip

allen edmonds mcallister review

Next, the most common shoe on this list, the wingtip. This one is undoubtedly the style that the average man will gravitate towards when they are looking to buy a dress shoe in a store. Not every man’s wardrobe consists of only wearing suits. It’s a great investment to have a pair of shoes that looks just as good off the clock as on.

chambray shirt dressed up outfit

With so many choices in the market, my recommendation is to find a medium brown or cigar colored pair. You can wear them with navy, grey, maroon, ochre… the list goes on. A wingtip might be the first pair of dress shoes to buy if you find yourself in need of a versatile shoe that can be worn with a pair of denim. If you’re looking to for a great pair that won’t break the bank, try these Beckett Simonon Yates or these Allen Edmonds Mcallister that Brian swears by.

3. Oxblood Cap Toe

pinstripe suit outfit ideas

If you read my piece on How to Style Oxblood Shoes with a Suit, you’ll already have a clue as to what my third pair of shoes is to round out my trinity. The color oxblood is a versatile and luxurious color that fits in with 90% of all men’s clothing. It’s the type of shoe that can break up the monotony of wearing just brown and black. Whatever style oxford shoe you prefer, oxblood’s rich look leather is a great investment, especially around fall when you’re reaching for heavy grey flannels and chunky tweed jackets.

Adding another cap toe to this list because sometimes less is more. With so many style options available in the market, oxblood should be on your list if you’re looking for a shoe that punches above its weight. This pair pictured below is the Melton from Johnston & Murphy.

best oxford shoes

What do you think about the list? Would you suggest 3 different shoes for your trinity?

Stylishly Yours,

Steven D. Elliott
He Spoke Style

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  • Tom B

    Great article, Steve! I’d argue with your order (buy the wingtips first), but not with the choice – these are definitely the three “wheelhouse” formal shoes any man should get. And you’ve touched on the most important point – if you take care of these shoes, they will last you forever. Get a shoe care kit, sit down and shine your own shoes, it’s relaxing (no, really!) and you’ll look great. Thanks for the write-up.

    • Steven Elliott

      Great point Tom. I think owning a shoe shine kit and learning what it means to keep things nice was a first step in my growth in mens clothing. Also reminds me, I haven’t scoured eBay in some time. Perhaps it’s time to take a look at a 2nd hand pair of something… stay tuned.