#2183 The Seven Pairs Of Shoes Every Man Needs

Jack Purcells, Mark McNairys, Chuck Taylors.

Jack asks: I’m overhauling my closet and starting with shoes. What, in your opinion, are the best basics/staples I should get?

Hi Jack, good question. I wear the same pair of navy blue Chuck Taylors every day of the week, and they are, in my opinion, the perfect shoes. However: I will concede that I don’t have to go to an office for work, my only dress code is whatever I feel like wearing on the day, and I wouldn’t wear them to a wedding. So after a bit of thought, I have come to the decision that there are seven pairs of shoes that should keep you (and every other man) well-shod no matter what the occasion. They are…

J Crew Preston Wingtip Oxford.

Black Leather Dress Shoes. I know everyone is always talking about how great brown leather shoes are – and I’m not disagreeing – but for formal occasions, I prefer mine black. I think they look better with navy and charcoal suits, and if you buy a quality pair and keep them in good condition, you’ll have them forever. I have a pair of Loake brogues that I only ever pull out for weddings, but they kill it every single time (if I had a job that required me to wear a suit, I’d rock them on the regular). Spend a bit of money on these – you’ll get it back in cost per wear.

Mark McNairy Navy Bucks.

Mark McNairy Navy Bucks. If you’re a sneaker wearer, these are your ultimate transition-to-adulthood shoes – they look great with rolled jeans, khakis or pressed pants with a heavy cuff, and they’re sturdy enough to wear daily without having to worry about messing them up (and if you do, just wait till the dirt is dry and brush it off). The only problem with these is that they look better sockless, and that’s a commitment in itself – mine gave me blisters for weeks.

Clarks Desert Boot in Beeswax Leather.

Clarks Desert Boots in Beeswax Leather. When I worked at Little Brother back in the early to mid-00s, we used to sell these amazing brown leather messenger bags. Nothing frustrated me more than when men would come in and ask if we had any out the back without any marks. Leather marks – it’s the nature of the beast. The more you use it, the more it develops. Clarks’ Desert Boots in beeswax leather are the ultimate if you want to make a pair your own. These bad boys get better every time you put them on. Plus, if you live in a place that doesn’t have a crazy winter (aka New Zealand), this is the only pair of boots you’ll need. Try them with dark chinos rolled above the ankle, and a dark pair of socks. And ladies, these look just as good on you too.

Timberland Boots in Heritage Leather.

Timberland Boots. I got obsessed with Timberlands when I saw the guy who works at Oak NYC on Bond Street wearing a pair with some skinny blue jeans. Then Drake wore a pair when he performed at the NHL All Star game and I was sold. They’re my favourite all-weather boots – they’re warm, they’re waterproof, they keep out the mud – and they give you automatic swagger because they’re the heaviest things you’ll ever put on your feet. Stomping is guaranteed. Get them in the heritage leather – it’s far more attractive than the regular mustard. Ladies, these look even better on you.

Loake Chester Brogue.

Brown Brogues. Because they look this good. These ones are by Loake and I think we should all get a pair.

Ovadia & Sons Double Monk Straps.

Dub Monks. I don’t own a pair myself, but whenever I see well-dressed men walking around town in them, I feel jealous. Thanks to Lawrence Schlossman and the menswear bloggersphere they’ve become the buzz-shoe of the past 12 months, and for good reason – they’re a bloody great looking pair of shoes. I like them best with hefty grey flannel pants, a solid cuff and plenty of ankle. NB: I’m not 100% on the whole leaving the top buckle unbuttoned thing, but if you can pull it off, more power to you. If you’re unsure, don’t do it. This pair is by Ovadia and Sons and is available here.

Converse Chuck Taylors in Navy Blue.

Navy Blue High Top Chuck Taylors. Literally the ultimate shoe ever created. I couldn’t recommend them more enthusiastically.

Special mentions: New Balance US574s, Vans Authentics in offwhite with the blue trim, Nike Killshot Twos, Jack Purcells.


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  1. Jenny says

    That is a handsome collection of shoes. And oh, so much more wearable than most women’s shoes. I would love to see a photo of each pair with your recommended pants!! Cheers, J

  2. isaaclikes says

    They do when the shoes are faded out but can look a bit funny if it’s all the same colour.

    Sent via BlackBerry from T-Mobile

  3. boganpete says

    “If you’re a sneaker wearer, these are your ultimate transition-to-adulthood shoes” – says the guy who only wears played out scruffy Chuck Taylors. So when you gonna grow up?

  4. Emma Gleason says

    I’ve desperately wanted Timberland boots for about three years. This might be the winter I commit.

  5. Hope says

    your boring me Isaac, please give us some relationship advice , a great story, or some awesome new music. 

  6. isaaclikes says

    Yeah. Jeans, skirts and tights, basically everything except your prom dress.

    Sent via BlackBerry from T-Mobile

  7. says

    I like your footwear code. I work at home so most of the time I wear my blue cons too. I have black leather shoes for the occasional party, and flip flops for Summer.

  8. Amanda says

    Thanks for the Timberlands/Clarks heads up Isaac, might get a pair to take down to Queenstown for apres ski and walking round town in the daytime with leggings and jeans!

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