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Last week we gave you our Guide to Buying Shoes where we taught you how to distinguish quality when you step into a store. This week we want to teach you how to build the base of your footwear collection. With so many choices in every possible color, shape, and material it’s pretty hard for a guy to start from scratch. That’s why we’ve cut it down to the 5 shoes that every guy should have in their closet…

The Brown Wingtip

Crockett and Jones Clifford Wingtip, $695

This is the first shoe you should buy. The brown dress shoe is the shoe you will wear with your grey and navy trousers, and thus a shoe you will wear very often. This is also the shoe that you should not skimp on. Invest in a quality wingtip and you will not regret it. It will be the centerpiece of your footwear collection for years to come. You want something slim, but not too slim, and with gorgeous, preferably antiqued, leather. There are a few options you should check out when looking into a quality wingtip, and they will all cost you. Of course, you could go with Church’s–their reputation for quality footwear speaks for itself. There is also Barker Black, which we promote all the time–their Archdale wingtip is one of our absolute favorite shoes. But we want to point you in a different direction this time.

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This is an ambitious Piece by Piece, but it’s really just to give you an idea of all that’s going on in Cary Grant’s style. No one executed it as well as him. Masculine but playful. Smart but fun. Classically American, so we stick to some Americana (but for the shoes).

J. Press 3-button Wool/Cashmere Blend Sport Coat in Olive Tweed

J. Press 3-button Wool/Cashmere Blend Sport Coat in Olive Tweed


Paul Stuart Sussex Pinpoint White Dress Shirt

Paul Stuart Sussex Pinpoint White Dress Shirt


J. Press Silk Ascot

J. Press Silk Ascot

Paul Stuart Parquet Pocket Square

Paul Stuart Parquet Pocket Square

Paul Stuart Tan Tropical Weight Wool Trousers

Paul Stuart Tan Tropical Weight Wool Trousers

Paul Stuart Pebble Grain Belt

Paul Stuart Pebble Grain Belt

Loake Kew Captoe Oxfords

Loake Kew Captoe Oxfords


Paul Stuart Panama Straw Hat

Paul Stuart Panama Straw Hat

This is just one side of Cary Grant’s famed style — a bit more summery (despite the tweed, it’s still heat friendly), and more on the To Catch a Thief end of the spectrum. It requires a prototypically American style jacket, and such a jacket could only be a 3-button sack sport coat (That means it needs a third button at the top but so the lapel actually folds over and almost disguises it so that only the middle button is meant to be buttoned — a uniquely American jacket that literally fits like a sack, and which was once very popular, and often sported by Grant himself). J. Press has a monopoly on this jacket, and it’s for good reason: while every company has since turned to more contemporary one and two button looks, J. Press is the sole surviving expert on the issue. Throw on a modest white shirt in lightweight pinpoint, but make sure that collar has some size so that when you stuff the J. Press ascot underneath, your collar folds against your jacket lapel without going over it. We love the polk-a-dotted navy ascot for a truly Grant look. But again, underneath the shirt, whose top button or so should remain unbuttoned to reveal that ascot. Throw in a pocket square haphazardly, and toss on some gentlemanly trousers in a super lightweight wool with a classic fit. We could have gone with a linen pair of trousers, but linen with a wool jacket is questionable, and since this is a more Grant-in-the-summer look, we figured the Paul Stuart tropical weight woolens were the perfect compromise. Keep your pants on with a light brown pebble grain belt, and match the belt with Loake shoes. Feel free to cap it off (no pun intended) with a tropical-friendly straw hat.

J. Press 3-Button Sack Jacket, $795 at J. Press.
Paul Stuart White Pinpoint Shirt, $148.50 at Paul Stuart.
J. Press Ascot, $89 at J. Press.
Paul Stuart Pocket Square, $69.50 at Paul Stuart.
Paul Stuart Tropical Weight Wool Trousers, $344 at Paul Stuart.
Paul Stuart Belt, $128.50 at Paul Stuart.
Loake Captoe Oxfords, $240 at Loake.
Paul Stuart Straw Hat, $167.50 at Paul Stuart.

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