The 5 most versatile leather shoes a man can own

They say you should spend money on your shoes and your bed, because if you’re not in one, then you are in the other. And even if it turns out that this is the marketing department of Common Projects, it does make some sense. Shoes are, after all, the staple of any outfit. A good pair can enhance your look; and a bad pair will drag it down. Not only that, but well-made shoes will last better in the long run. Assuming you don’t run into it, of course. But unless your shoe budget exceeds Carrie Bradshaw’s, you’ll want to invest the money you have in the strongest options possible. The ones that will give you more mileage than Sir Ian Botham doing a charity walk with The Proclaimers. Which you almost never can go wrong with. With that in mind, we’ve rounded up the most tireless workhorses – and they’re all leather, because if your shoes aren’t leather, you’re not really trying hard enough. These five flexible pairs ensure maximum return on your investment, so be prepared to downsize your shoe cabinet and maybe rent the reclaimed space on Airbnb.

1. Minimal white sneakers

First of all, they are white which goes with everything. Or will do as long as you keep them clean: Damaged sneakers will kick smart looks onto the pavement faster than you can say “shitty nightclub bouncer”. A minimalist design also gives you maximum styling options. Again, if you think about the “neatness” of a suit and a shirt, a sneaker with clean details is just more comfortable. It’s a similar rule for texture: rougher textures are – in general – informal, while smooth fabrics appear dressier. Too many bells and whistles on your sneakers will ring the wrong note. And they won’t be good at sneaking around either. That’s why leather sneakers are the smartest. They are smoother, shinier and therefore more formal than canvas. In addition, they are easier to clean (see above). Leather sneakers also tend to be thicker, which compensates for the heaviness of tailored clothing or bulkier jackets like a trendy sheepskin bomber. Considering all of the above, when it comes to versatility, the adidas Stan Smith is, like the tennis ace who lent it its name, hard to beat. Although maybe less now – he’s in his sixties.

Casual lookbook inspiration

simons 2015 burton aw15 el burgues aw15 mango man aw15

Inspiration for a smart lookbook

Men's White Leather Sneakers Chic / Formal Outfit Inspiration Lookbook

j.crew october 2015 burton aw15 mango man 2014 windsor ss15

Key styles

Medium brown or dark brown oxfords

Brogues began as shoes worn by Irish and Scottish farmers to cross bogs. are all-purpose and all-purpose shoes. Indeed, as we have already discussed, they are invaluable in negotiating the quagmire of the dress code which is chic and casual. That said, you’ll want to consider your footprint. Brogues that are too thick or too round won’t look stylish enough for a standard worsted wool business suit (although they can pair well with a sturdy tailoring in a heavy heirloom fabric like tweed or flannel). Likewise, brogues that are too thin and pointed will not resist quality jeans. So what is the ideal? An intermediate “almond” shape will perfectly match the chic and relaxed line. The broguing itself, however, is a whole other factor. Remember: In general, the larger and / or wider the holes, the more relaxed the shoe. So opt for a semi-brogue (perforated toe cap, but no wings) if you are looking for a style for all occasions. Black brogues are a bit too harsh for chic casual outfits, but lighter than medium brown and they’ll be a bit too casual to wear with formal outfits. Speaking of which, tanned brogues with a dark or formal suit make you look more chic than a hapless contestant on The apprentice who does not know the meaning of the word ‘fail’. As in “the failure of the holding”.

Casual lookbook inspiration

Brogue Casual Lookbook

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Inspiration for a smart lookbook

Elegant brogue lookbook

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Key styles

Penny Bloodblood Or Black Loafers

Like brogues, moccasins are a real chic and relaxed lifeline. They descend from a moccasin-style shoe worn by Norwegian fishermen, so their DNA is as relaxed as the word ‘bread’ suggests. But then, in 1934, GH Bass – the OG of moccasins – refined them a bit by remaking them in leather, with a thicker sole. They have become a staple of Ivy League students precisely because of their ability to seamlessly switch between chic and casual. However, there are a few things to keep in mind before you buy. As with brogues, a rounder toe is more relaxed, while a sharper silhouette points more to an equally crisp outfit, so look for a happy medium for maximum wearing opportunities. You would also be advised to pay attention to the gap. If the upper – the leather upper that runs from toe to toe – is too short or “low”, then you’ll be showing way too many socks for formal wear. And your foot will look oddly small. Finally, the profile of loafers can be a bit thin to pair with a super structured suit or looser, so look for a chunkier-sole style if that’s what you’ll wear them with most often. Otherwise, tapered pants will be on the money.

Casual lookbook inspiration

Casual loafer lookbook

scotch & soda AMSTERDAMS BLAUW FALL 2014 j.crew october 2015 office ss13 faconnable aw15

Inspiration for a smart lookbook

Smart loafer lookbook

tommy hilfiger ss14 mango man winter 2014 aquascutum ss15 boss hugo boss pre aw15

Key styles

Black Chelsea Boots

Similar to loafers, the carefree donning of Chelsea boots makes them more casual than your usual leather laces. It might be the Beatles’ association, but there is something rock’n’roll about the plain black – and therefore technically smart – leather Chelsea boots that make them a viable accessory for a biker jacket. At the same time, that black leather will make them dressy enough to be worn with a costume, like the Rolling Stones in those early images where they were all respectable. If you are influenced by suede, keep in mind that what you have to gain in fluffy texture, you will lose in formality. And impermeability. Again, the weight will help you gauge which end of the smart-casual spectrum they are on. A particularly sharp style can make your feet look gigantic, especially with slim or skinny jeans. For this reason, among many others, you might want to adopt Kanye’s look and “stack” your jeans to balance. However, you should definitely not stack your dress pants, unless you really want to look like you borrowed them from your dad. And don’t wear them with a four-button suit, unless you want to look like the Fifth Beatle who was cryogenized like Austin Powers.

Casual lookbook inspiration

Casual Chelsea Boot Lookbook

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Inspiration for a smart lookbook

Stylish Chelsea Boot Lookbook

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Key styles

Black derby shoes

Shoe fetishists will tell you that derbies are distinguished by eyelets sewn on the top of the vamp and “open”, making the silhouette a little less refined than that of brogues and therefore the whole a little more relaxed. Americans sometimes call Derbies Bluchers, although there is technically a slight difference between the two. But they also call wing tip brogues, so what do they know? Despite this casualness and an often stockier profile than Oxfords, derbies also have a certain minimalism in their otherwise intact upper, which is both sleek and modern. They aren’t as stuffy as brogues or as foggy as brogues. We’d tell you to temper this bulk if you pair them with a suit, but Brunello Cucinelli purposefully pairs beefy derbies with tapered suits to create a stark contrast. And it’s also precisely because of this bulk that they look great with a T-shirt, jeans and a biker or bomber jacket, in a way the Oxfords just don’t. We’re going to take risks here, but black derbies just might be the most versatile and fashionable shoe around.

Casual lookbook inspiration

Casual Derby Lookbook

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Inspiration for a smart lookbook

Smart Derby Lookbook

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Key styles

Last word

Have you covered all of these bases? Or is there a pair of leather shoes that you’d vote more versatile than the five we’ve highlighted? If so, tell us below.


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