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The Ultimate Shoe Collection: Must Have Shoes For Men

The Ultimate Shoe Collection: Must Have Shoes For Men

19 Apr 2023

The Ultimate Shoe Collection: Must Have Shoes For Men

By James Shackell

So you’re ready to graduate from dodgy sneakers to a proper leather shoe collection. Good for you! It’s an important step in every guy’s evolution from scrappy 20-something to suave, 30-something grown-up. Outfits are important, and all outfits start around your ankles. But there are dozens of men’s shoe types out there, so where to begin? How many pairs of shoes does one guy really need? And which ones are the most important? That’s what we’re going to tackle here

What Makes A Good Shoe Collection?

The whole point of building a well-rounded shoe collection is flexibility. You want one or two shoes for every social occasion life throws your way. Try and be smart about it, too. A pair of Chelsea boots is an excellent investment because Chelseas can be worn almost anywhere, from the office to the barbecue. You’re sort of getting three shoes for the price of one.

A mix of shoe types also means you’re not wearing the same shoes every day. And that’s a huge deal. Ever wonder why your leather shoes tend to die within six months? It’s usually because you wear them into the ground. Leather is a natural material, and it needs time to recover and breathe after each wear. Having a versatile shoe collection means you can keep your shoes on a constant rotation, which will dramatically extend their lifespan.

How Many Shoes Does One Guy Need?

When does a shoe collection become a shoe obsession? That’s really up to you. If your house has become more of a shoe shrine, and you’re finding yourself sacrificing other luxuries, like food and electricity, it might be time to slow down your footwear habit. For most guys, we reckon six to eight pairs is a nice sweet spot. It’s a manageable collection, but there’s still tonnes of room for variety.

Shoes for the Office

Let’s start with shoes for the office, or business shoes. Obviously this will depend on your office and company culture. Corporate offices need fairly conservative dress shoes, like Oxfords or Derbies in brown or black leather. The BRENNIN, HARLEN and BERESFORD are all good places to start. To make your collection stretch further, it’s usually a good idea to get a couple of pairs of dress shoes – maybe one pair of black Oxfords, and some brown Derbies with broguing. Not only will this keep you from wearing the same office shoes every day, but you’ll have something to throw on for weddings and formal events, too.

Shoes for the Weekend

This is a pretty broad category. You need shoes that will handle multiple occasions: footy, pub lunch, backyard barbecue, country winery, running down the shops, basically everything. For weekend casual, we recommend one pair of either sneakers, Chukka boots or Chelsea boots, depending on your preference. Chukkas are a good middle-ground option, because you can dress them up or down. A mid-ankle boot like the ADAMS or the BRODY will work with slim-fit jeans, chinos or even cotton shorts. Just throw on a button-up shirt or loose-fit crew neck tee. If you’re going down the sneaker route, pick something neutral and versatile, like white DECO 2.0 trainers.

Shoes for Formal Events

If you’ve followed our advice above, then you already have one or two pairs of dress shoes for the office. These will certainly work for most formal events, but you need to give a bit of thought to the dress code. ‘Black tie’ for example, usually means patent leather black dress shoes, like the STONEHAM, although you can probably get away with some black TOMMASI Oxfords. The most flexible formal shoe is arguably the Derby, since it can be styled for the office, the wedding, the cocktail party, and everything in between. If you can only fit one pair into your collection, make it something warm and classic, like brown BENNET brogues. These guys will work with navy suits, charcoal suits and even suiting separates.

Shoes for Date Nights

Date nights can range from fancy restaurants to bowling and beers, which is why you need a versatile shoe collection. If it’s a more casual date, your weekend sneakers or Chukka boots will work fine (just make sure they’re clean before you step out the door). Formal occasions and anniversaries might require something a little more sophisticated, which is where your brown Derbyies can really shine. For everything else, we find a pair of black Chelsea boots usually does the job. Some DEXTER Chelseas will work on almost any date. Just style them with black slim-fit jeans and a sharp button-up shirt. If you want to make your Chelseas stretch further, a more formal boot, like the BRONSON, can go all the way from date night to corporate boardroom.

Shoes for the Beach

The only thing missing from our shoe collection at this point is summer slip-ons, or shoes for the beach. When the weather heats up, you really need a lightweight slip-on shoe; ideally something that can go from sand to the shops. You’ve got a few choices here. There are leather sandals, easy pool slides, like the PLAYA, men’s espadrilles, boat shoes and driving shoes. Pick one of these categories, to start with. Whichever you think will give you the best mileage and work with the most outfits. A woven neutral espadrille, like the CABO, is an excellent choice. You can style these with swim shorts or cotton shorts, and then either a linen shirt or a simple crew neck tee.

Our Collection

So let’s take a quick look at our collection. We’ve got one pair of black Oxfords, for formal occasions. One pair of flexible brown Derbies. One pair of black Chelsea boots, for date nights and semi-formal events. One pair of sneakers and one pair of Chukka boots, for weekend wear. And one pair of leather espadrilles for summer. That’s a pretty solid core to build your collection around. There’s something for every occasion, and you can keep each shoe on regular rotation.