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Looking To Improve Your Shoe Game? Start Here.

December 29th, 2017

Four of my favorite styles from Johnston & Murphy

In partnership with Johnston & Murphy.

Making the decision to get serious about improving your style is easy. Knowing where to begin, what brands to buy, how much money to spend, well, that’s the hard part. Like me, you’ve probably been there, or perhaps you’re reading this post because you’re on your way to getting there. Today, we’re focusing on one of the best places to start developing a better wardrobe. And that’s from the ground up.

Footwear is the anchor of every outfit and, as such, should always be high on your priority list. Too often, however, it seems to be an afterthought or not a thought at all. Sneaker-dress shoe hybrids don’t go with anything – not jeans, not chinos, not a suit. If you have a pair, do everyone a favor and throw them out now. A hybrid shoe like that isn’t versatile, it’s just wrong.

One thing to keep in mind as you think about making a foray into footwear is that good shoes cost money. Are all good shoes in the $600-$1,000 price range and should you have to shell out that kind of cash for good shoes? The answer is, no, on both counts. Footwear is just like clothing in that sense that you can find quality shoes at a variety of price points.

Now, it’s fair to assume that when you’re taking those first steps into serious menswear, you are probably going to be very picky about how you spend your cash and how much of it you spend. I know I was. And when it came to footwear, I’ve always been keen on finding the best at a realistic price point. And honestly, to this day I’ve never spent over $500 on shoes (except for my wedding loafers…).

When I was just cutting my teeth and this site was in its infancy, one of my first nice pairs of shoes was an oxblood wingtip by Johnston & Murphy. I loved them and still wear them to this day – you’ll actually see them below. I’ve recently had the opportunity to get acquainted with a wider selection from the J&M line and today I’m sharing four of my favorite styles, which are perfect picks if you’re wondering where to start.

Everyday Boot: Conrad Cap Toe Chukka

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In a way, choosing a shoe for a suit or blazer/trousers outfit is pretty simple. Choosing a shoe for casual outfits tends to be more difficult. So instead of a shoe, consider a boot like a leather chukka. A leather chukka, such as the Conrad Cap Toe, is a great option for everyday wear. It’s an easy way to subtly dress up your slim dark denim while being an equally nice solution to giving a pair of chinos a little rugged, no-nonsense elegance.

Johnston & Murphy Conrad Cap Toe Chukka, $179

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All Business: Boydstun Wingtip

As I mentioned, my first pair of Johnston & Murphy shoes were an oxblood wingtip, which I’ve worn a lot over the past four years though I’ve yet to wear them out. This is what you’re looking for in a new pair of shoes. Wingtips aren’t just a dress shoe and are actually incredibly versatile. Comb through the archives and you’ll see them styled with a suit, of course, like you can see here, though they get equal wear with sharp casual looks as well as edgier ensembles with denim and a leather jacket.

Part of their versatility (not to mention comfort) is due to the leather as well as their rubber sole. While my “old” pair is not currently in the J&M lineup, the Boydstun wingtip is a more than adequate equivalent. The Boydstun has a leather sole with rubber tread insets, which does nothing to their versatility but makes them even more appropriate when you’re suiting up.

Johnston & Murphy Boydstun Wingtip, $139.99 (currently on sale)

Timeless Loafer: Deerfield II Tassel Moc-Toe

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Next to a wingtip lace-up, every man needs a great pair of tassel loafers. Not only do they possess an elegant and timeless style, but they really telegraph to the world that you “get it” when it comes to classic and permanent style. One of the things that has always impressed me with Johnston & Murphy shoes is the comfort your feel straight out of the box and the Deerfield II tassel loafer is no exception.

Part of that is due to their Exclusive Trampoline Comfort System with its toe-to-heel EVA mid sole and resilient Poron-foam and full leather lining offer superior cushioning. Another part of the Deerfield II’s appeal is its Goodyear welt construction, which I’m sure you know, allows the leather to mold to your foot over time, making for an even more custom and comfortable fit.

Johnston & Murphy Deerfield II Tassel Moc-Toe Loafer, $279

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“New” Classic: Aragon II Kiltie Tassel Loafers

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I really believe that the kiltie tassel loafer is poised to have a serious moment. As I mentioned in our post dedicated to the style, the kiltie tends to get pigeonholed as an old man shoe. But, as I also mentioned, your grandfather didn’t wear kiltie tassel loafers because he was an old man, he wore them because he had style.

It’s a little difficult to find a quality kiltie tassel these days, which is what makes Johnston & Murphy’s Aragon II even more special. These have honestly been one of my favorite pairs of loafers this season as they work so incredibly well with a mid-grey flannel trouser, which has been a key part of my uniform lately.

Johnston & Murphy Aragon II Kiltie Tassel Loafers, $99.90 (currently on sale)

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Chime in: Which is your favorite pair?

Stylishly Yours,

Brian Sacawa
He Spoke Style

Photography by Rob McIver Photo

Brian Sacawa

Brian Sacawa is the Founder of He Spoke Style and one of the original men’s style influencers. Since 2013, his goal has remained the same: to provide men the advice and inspiration they need to dress well, develop their personal style, and gain more confidence. Brian’s interest and passion for men’s style and luxury watches has led to his writing for The Robb Report, The Rake, and Sotheby’s and he has been quoted on menswear in publications such as The New York Times, The Wall Street Journal,, Brides Magazine, and the Huffington Post. He lives in the woods north of Baltimore with his wife, Robin, kitties Nick and Nora, and German Shepherd/Collie mix Charlie.

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