New Year’s gives everyone a chance to take stock of where they are — for better or worse (I’d vote better). You’re forced to check in and say: how are we doing here? One place a lot of guys start is the closet: clean out the junk, see where there are holes. A resolution of mine? To wear slacks every day.
But I’d argue the most important place to start for any wardrobe is at the bottom — the shoes. A good pair of shoes is where it all begins. They can make an outfit. A bad pair and it doesn’t matter what the other 90% looks like — you’re cooked.
If you have those goofy loafer-sneakers that half of Wall Street tried to convince themselves look good, post COVID stop. Put down your phone. Throw them away. Then come back and join us.
Good. Now that that’s done, let’s lay the foundation.
Whether you wear a suit every day or not, you should own a proper pair of oxfords. They will come in handy. Brown or black doesn’t matter, but keep them simple and reach for cordovan if you can.
Pro tip: If you get a good black pair with a proper shine, you can get away with wearing them with a tux.
I’ve looked far and wide for oxfords and I’m very particular — I like them clean, narrow, and in cordovan.
Carmina – If you can afford them
Meermin – same family, more approachable price point
Crocket & Jones - Classic English boot making
Every guy should own a loafer, and most do. The spectrum runs from casual drivers to serious penny loafers like Alden or Ferragamo.
Casual
Tod’s – the original driving shoe (those heel nubs are there for a reason)
Todd Snyder x Alden – Criminally on sale right now; if they have your size, buy them…I just did.
J.M. Weston - French Winner
Work
Alden – a New England company through and through; the best shoe on this list
Gucci – you’ll get looks the occasional eye roll; Ive never been able to work up the confidence. But perhaps you can? If your an entry level analyst maybe don’t but they are objectively great.
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Ferragamo – never spoken to me personally, but every guy with a serious closet owns a pair
Chukka, desert boot — call it what you want. The style traces back to British soldiers fighting wars in the desert who needed a rubber sole. Still undefeated.
Crockett & Jones – just got a pair for Christmas and I’m fired up
Sabah – newer to the category, more casual, first real non-slipper shoe they’ve made
Drake’s (Clifford Desert Boot) – of course they nailed it
Every guy should own a Chelsea. They’re durable and always look right. I own suede, but I wish I had gone leather years ago for a real workhorse. Use suede for desert boots instead.
Meermin - Affordable
R.M. Williams – Australian, a bit more polished than Blundstone
Blundstone – probably the shoe I wear most in winter
I’m not talking Air Jordans. I mean classics you can wear on a date or to a ball game. Sneakers shouldn’t be the everyday resist the urge and reach for them when needed.
Three classics:
Once you’ve laid the foundation, these come into play:
Belgians – fit like slippers, elegant enough for the most discerning rooms
Stubbs & Wootton – Palm Beach staple for those in the know
Xtratuf – bought for a Nova Scotia sailing trip, now worn constantly
Hunter Wellies - I’ve debated which brand to go for Wellies after a recent trip to London Its clear its Hunter
Wallabees – different from a desert boot, absolute classic
Sabahs – don’t wear flip-flops; no one wants to see your toes
Birkenstocks – never thought I’d wear them, now I love them
A Few Last Thoughts on Shoes
Invest in quality. It hurts to spend $700+ on a pair, but with good leather, regular shining, and resoling, you can own them for 20–30 years.
Shine your shoes. If you have leather shoes, take the time. It’s a forgotten tradition and one of the great small pleasures in life. Always bring cash and always tip — those guys work harder than almost anyone in the city.
Buy shoe trees. They pull out moisture, keep the shape, and easily double the life of your shoes.
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Buy the right sock for the job and Bombas for casual - Sid & Mashburn for dress and never below the ankle
