For those just starting their fashion journey, a common question often arises: “Am I following the ‘rules’ of dressing properly?” Here's the thing about fashion: while there are principles to looking sharp, the beauty lies in how those rules can evolve—and sometimes be broken—based on the occasion and your own sense of style. Take the once-radical idea of pairing sneakers with dress pants or a suit. Now, it's a go-to move for many.
Below, you'll find a guide on how to pair shoes with the most common types of men's pants, keeping in mind that fashion is always changing. Hopefully, this advice will still hold up in the years to come.
Chinos
Chinos are a wardrobe staple for good reason - they're comfy, versatile, and effortlessly shift from casual to smart-casual. For that reason, loafers or boat shoes (especially in warmer weather) make a perfect match for chinos.
What you’ll want to avoid are velvet slip-ons, as their texture clashes with the casual vibe of chinos.
When it gets colder, don't shy away from pairing chinos with lace-up boots. It adds a bold, dynamic edge to your look.
Joggers
Made from soft cotton and featuring a cuffed ankle, joggers have become synonymous with sneaker culture. While they are super comfy, this can be a downside when paired with the wrong shoes. Avoid slip-ons, espadrilles, or penny loafers with joggers - they tend to make the look seem too juvenile.
Stick to your sneakers when rocking joggers. A clean, sleek pair will keep things modern and stylish.
Another underrated option? Suede desert boots. Their casual yet refined style works surprisingly well with joggers for an offbeat, cool look.
Dress Pants
Dress pants call for classic options like derby shoes or brogues - ideal for a professional or formal setting. But what about when the weekend rolls around? You still want to look sharp but feel more relaxed, so swap out the dress shoes for minimalist sneakers. Roll up the cuffs for a smart-casual twist that works perfectly for laid-back days.
Suits
A notch up from dress pants, a full suit deserves shoes that match its sophistication. Traditional choices include Oxfords, derbies, or brogues - just make sure they’re polished and clean to keep the look on point.
That said, while these shoes are timeless, they can feel a bit predictable. If you're feeling bold, try pairing your suit with Chelsea boots or minimalist sneakers for a modern and trendier vibe.
Jeans
Jeans are easily the most versatile pants out there, and they can pair with almost any shoe. In colder weather, there’s nothing quite like slipping on a pair of Chelsea boots with your jeans - whether they're leather or suede, they add a level of refinement. Or, if you prefer a more laid-back style, cuff your jeans and wear them with sneakers.
If you're looking to dress up your jeans with something more formal, steer clear of overly polished styles like Oxfords to avoid a jarring contrast. Instead, opt for basic lace-up derbies, which strike the perfect balance between casual and smart.
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