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Stop playing it safe: The confident guy’s guide to bold shoes

Let brand president, Mike Kelly, teach you how to wear unique shoes

TAFT woven boots on curb
Mark D. McKee / The Manual

Sometimes men’s clothes can get boring. They can get stale. Walk into any men’s clothing store and you could drown in a sea of blue. We sometimes settle into our blues and grays and have difficulty expressing ourselves through our appearance. Maybe it is complacency. Perhaps we lose our confidence. Whatever it is, finding a way to stand out from the men who tend to fade into the background is a skill every guy needs to learn by the time they are in their mid-30s. This is when we are told to sit down and be quiet. But, there are ways to stand up and be seen, speak up and be heard, without any movement or any words. TAFT is a company that specializes in men’s shoes and how to make them your statement piece. They can send a message before you even introduce yourself to someone new. I was able to sit down with TAFT Brand President, Mike Kelly, to get an idea of how to wear shoes as a statement instead of a function.

“Let’s be real—guys like getting compliments just as much as anyone else,” Kelly says. “TAFT designs shoes that get noticed, not because they’re loud for the sake of it, but because they’re different in all the right ways. It’s about helping men feel confident, express themselves, and bring a little personality to the everyday.”

Making a statement

Standing out is fun when you do it right, but you can look like a try-hard when you do it wrong. When you are looking for something to help your outfit pop, do something small and simple to help you show off without overwhelming those around you. So, the best way to approach it is to take your boring wardrobe and let it be the canvas your unique shoes use to create a work of art.

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“Most guys stick to neutrals—think black, white, grey, navy—and that’s totally fine,” Kelly says. “It actually sets the perfect stage for your shoes to stand out. If you keep the rest of your outfit clean and simple, a bold, unexpected pair of shoes becomes the centerpiece without trying too hard. Eyes will go straight to your feet—in the best way possible. It’s the easiest way to elevate your look and show some personality.”

Breaking the ordinary

There are some classics that go on your feet. Some of the best men’s shoes are basics that have an undying style—something like an Oxford, which James Bond made look stellar for six decades. Or maybe you love a good government-issued wingtip. If you are a boot guy, there are some legendary looks you can get that will anchor your footwear forever. Letting your shoes speak for you with something unique doesn’t mean abandoning tradition. On the contrary, it means putting a slight twist on the classic and breaking out of the ordinary, and in some ways, breaking out of the boring norm we can so easily get lost in on a daily basis. Kelly explains how to ease your way into it.

“Every man needs a versatile pair of dress shoes, but that doesn’t mean you have to stick to the same tired black oxfords. Start by stepping just outside your comfort zone—think a rich brown boot or a sharp loafer. Once you experience how a bold pair of TAFT shoes can instantly elevate your everyday look, there’s no turning back. Trust me, the compliments will follow—and you’ll be reaching for even bolder prints and textures before you know it.” 

The confident you

Fashion is what you wear, style is how you wear it. I firmly believe that fashion is what guys get lost in when they try to elevate their wardrobe. Oftentimes, when their partner expresses the desire for them to look a little nicer when they go out, they start looking for expensive garments because they conflate fashion with style. Whatever you wear, the style comes with the confidence you bring to the look. If you love a pair of shoes, own them and wear them. In style, out of style, elegant, or garrish, don’t ever let someone tell you you can’t wear something. Experiment with it and see what you come up with. Kelly echoes this sentiment with his shoes from TAFT every day.

“It’s less about the occasion and more about the energy you bring. A bold shoe doesn’t need permission—it just needs the right attitude. Whether you’re in jeans and a tee or a tailored suit, the right pair can take your whole look up a notch. Style isn’t about following rules anymore—it’s about owning your vibe. So if something catches your eye and makes you feel like you, wear it. The confidence will carry it every time.”

I love a good loud shoe, and they will look great on you if you do it right. But if you take nothing else from Kelly or me, take this last idea and run with it. Confidence can get you through many things you may be afraid of or uncomfortable with. TAFT makes it easy to sit with that confidence and wear something unique every single day.

Mark D McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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