If you’ve ever noticed that men rarely sport puffer jackets at the beach or drizzle sriracha sauce over their ice cream, it’s for a straightforward reason: some things just don’t mix well together. This principle applies to clothing as much as it does to food combinations.
Take shoes and trousers, for instance. It’s pretty common knowledge that flip-flops don’t pair well with a tailored three-piece suit—unless, of course, you’re aiming to be shown the door at every wedding, job interview, or funeral you attend. However, the subtleties of footwear choices can be more nuanced, and not all mismatches are as glaringly obvious. Understanding these combinations can elevate your style and help you avoid social faux pas.
To make things easier for you, let’s break down the most common styles of trousers and the types of shoes that pair best with each. By doing this, we’ll take the guesswork out of your outfit choices, ensuring you look polished and put together no matter the occasion. Here’s a guide to help you make the right footwear decisions for your trousers.
What Shoes To Wear With Jeans
Jeans have become the go-to choice for most men these days. They seamlessly transition from casual weekends to more formal work settings, making them a staple in everyone’s wardrobe. Because they’re so common, it might seem like jeans can be paired with any type of shoe. However, that’s not quite the case.
While there are smarter styles of jeans available, they still don’t quite match up with formal shoes like Oxfords. Those are best left for indie bands or your boss at a casual staff outing. Instead, Chelsea boots are a great option for a more polished look with jeans.
If you’re wearing distressed, stacked jeans—like the kind Kanye West might choose—trainers are the way to go. Minimalist trainers are a safe bet, but if your jeans are on the more subdued side, you can experiment with chunkier, statement trainers. On the other hand, if you opt for straight, heavy selvedge denim—denoting a tougher, more rugged style—these pair better with thick-soled boots rather than trendy styles like Yeezy 350s. Understanding these combinations can elevate your overall look and ensure you’re stylishly put together.
What Shoes To Wear With Tailored Trousers
A decade ago, when it came to suits, your main decision was about how much break you wanted in your trousers—essentially how they fell over your shoes. But times have changed, and designers have gotten much more inventive. The suit is no longer just a uniform; it has become a canvas for personal style. Now, you have the option to mix and match your jacket and trousers, wear a double-breasted jacket unbuttoned, and experiment with different footwear choices. While classic black Oxfords or Derbies are still safe options—especially for formal occasions—there’s so much more flexibility now.
For instance, those white, minimalist sneakers that have been everywhere for the last ten years? They’ve become the perfect pairing for tailored looks. Wearing them with a slight gap between your trousers and shoes helps create a stylish balance between smart and casual.
If your trousers feature textures like tweed, heavy wool, or flannel, it’s important to choose sturdier footwear. Options like brogue or pebble-leather boots provide the right amount of weight and presence. You could even go for rugged boots that look ready for a mountain trek, even if your plans just involve a casual outing to the pub. This understanding of how to combine textures and styles can enhance your overall appearance, allowing you to express your personal style while still looking sharp.
What Shoes To Wear With Chinos
When it comes to preppy trousers, you should match them with equally preppy shoes. Think about the classic style of figures like JFK. For summer, opt for canvas sneakers; in winter, go for duck boots; and for all year round, loafers are a fantastic choice, whether you wear them with or without socks, depending on the weather.
If that preppy look feels a bit too Ivy League for your taste, consider brogues. They can add a touch of sophistication to your outfit and give you a more mature appearance. Just make sure the chunkiness of your shoes matches the weight of your trousers.
In winter, when you’re wearing heavier fabrics, you’ll want shoes that can stand up to the elements. Hiking boots have become trendy, even for those who consider an “adventure” to be a trip beyond the nearest cocktail bar. When choosing hiking boots, skip the flashy designs and opt for polished leather that real climbers would have worn ages ago. To showcase your boots, try rolling your chinos just above a pair of thick, woolen socks. This combination not only keeps you stylish but also practical for colder weather.
What Shoes To Wear With Joggers
Fashion can often lean towards the impractical, which is why trends like joggers are such a breath of fresh air. Joggers are not only comfortable and affordable, but they’re also incredibly versatile. With joggers in your wardrobe, you can eliminate the daily struggle of deciding what to wear each morning. They allow you to look stylish without sacrificing comfort, making them a trend worth embracing and cherishing.
With their sportswear origins and tapered fit, joggers are an ideal match for bold, statement trainers. This combination allows you to express your adventurous, space-age style while keeping your look balanced. The slim, neutral joggers act as a grounding element, ensuring that even the most eye-catching trainers won’t overwhelm your outfit. You can have fun with your footwear while still looking put together and stylish.
When it comes to dressing up, the options are often more restricted. While high-low dressing—mixing formal and casual pieces—is currently popular, there are still boundaries to consider. For example, pairing dress shoes with joggers crosses that line, and it just doesn’t work.
Chukka boots, however, offer a smart alternative that can complement joggers well. Made from suede, they add a touch of texture without feeling overly formal. Since these boots were originally designed for playing polo, they maintain a sporty vibe that blends nicely with joggers, ensuring your outfit remains stylish and cohesive without clashing.
What Shoes To Wear With A Tuxedo
When it comes to black tie attire, it’s important not to go too far off-script. Even celebrities like Jared Leto might experiment with bright colors or flashy accessories, but a solid, classic pair of shoes is essential to ground those bold choices.
If you want to make a stylish statement, consider wearing bowed slippers made from velvet or patent leather. You can match the texture of your slippers to your bow tie—whether it’s matte or shiny—for a cohesive look. For an even bolder approach, look for slippers with embroidered designs on the upper.
However, if you’d prefer to avoid drawing attention to your shoes and want to keep things traditional, classic patent leather lace-ups are the way to go. And if you find yourself in a bind, you can always give your Oxfords a mirror polish until they shine. This way, you can maintain elegance without worrying about questions or distractions throughout the evening.
What Shoes To Wear With Shorts
Most shorts are naturally casual, so it’s a good rule of thumb to choose casual shoes to go with them. However, that doesn’t mean you should just throw on any old, worn-out running shoes and head out the door.
The gap between your shorts and your shoes doesn’t help when trying to wear formal shoes like brogues, so it’s best to stick with trainers. Look for smart styles made from high-quality materials, which will keep your outfit looking polished rather than like you’re headed to the gym. You can also consider summer-friendly options like espadrilles, deck shoes, or sandals.
If you prefer to wear leather shoes, choose tailored shorts that fit as well as your suit trousers. This opens up the possibility of wearing penny loafers, which can look stylish. Just remember to skip the socks to keep the look fresh and appropriate for the warm weather.