Four Types of Men’s Shoes That Look Good On Anyone


If you were to take even a cursory glance at my wardrobe at any point over the last few years, one pattern would become eminently clear: shoes are my absolute favorite.

Not only is my shoe collection perhaps the only place in my otherwise-minimalist wardrobe where I’ve allowed redundancy (I own three discrete pairs of essentially identical low-cut white sneakers, but we’ll get to that), but it’s also far and away the section of my closet on which I’ve spent the most cash. When it comes to my personal footwear, I have zero tolerance for thriftiness: once you go Trask, you never go back.

But you don’t need to drop thousands of dollars on dozens of pickups in order to have a classy, versatile, and easy-to-wear selection of shoes to select from. In fact, if you ask me, most men only really need a few different types of shoes for the majority of circumstances, and they can each be acquired for as much or as little as you’re comfortable spending.

Whether you’re just starting out on your menswear journey or just looking for that one last pair of luxury boots to complete your collection, this list of four types of men’s shoes that look great on anyone can help give you direction when shopping for your next pair of must-wear shoes.

Number One: Low Cut White Sneakers

Low-cut white sneakers are truly a fashion panacea: with only a few exceptions, you can essentially slap a pair of these shoes onto most casual outfits and walk away looking put-together and contemporary. Jeans? Check. Cropped ankle pants with no socks? Awesome. Shorts? Yes, yes, even shorts!

The Aaron, is the Trask low-cut sneaker I own so many of. The luxurious Italian leather, aids in both the design of the shoe and the appearance.

That’s why I own so many slightly-different-but-essentially-the-same pairs of these: they’re ridiculously wearable, available at every price point, and especially when kept clean, make a great impression.

On the lower end of the cost spectrum, there are plenty of brands like Converse and Adidas making shoes that are stylish, inexpensive, and widely available. However, since these shoes are such a wardrobe staple, I find that investing in a high-end sneaker here is so, so worth it.

Ultimately, no matter which brand you pick, these are an absolute menswear must-have.

Number Two: Derby Shoes

Derby Shoes are a longtime menswear classic for a good reason -- when it comes to formal mens loafers, these are one of the most ubiquitous and classic looking options. But what sets Derby shoes apart from their close relative, Oxford shoes, is their versatility: it’s far easier to successfully dress these shoes down, so you can incorporate them into many more of your regular outfits no matter the occasion.

With other options on this list, I’ve recommended both inexpensive and high-end options, but for leather shoes, I’d really recommend spending the extra cash on a long-lasting, well-constructed pair. For a shoe like this, high-quality leather is really going to make an astonishing difference.

Fortunately, Hellman Clothiers has plenty of great options available: if you’re looking to add a pair of Derby shoes to your wardrobe and want to ensure you’re getting the highest quality construction, materials, and silhouette, there’s no better place in Cincinnati.

Number Three: Chelsea Boots

Whether you’re just heading into the office or out for a casual afternoon strolling through OTR, a well-constructed pair of chelsea boots will have you turning heads and catching second glances.

There’s just something about them: from the dead simple silhouette to the way they elegantly meet the cuff of a slim-fitting pair of jeans, adding these shoes to almost any outfit is a sure fire success. Especially in recent years, both suede and leather chelsea boots have become fashion essentials, and after one look at them, it’s easy to see why.

Once again, this is a ubiquitous enough shoe that I recommend investing in high-quality construction and noticeably luxurious materials, but there are also plenty of quality low-cost options available. Even further, there are plenty of similar alternatives to choose from, like our Armen Oehler Chukka book or Desert boots, so tailoring this look to your personal style is super easy.

Number Four: Espadrilles

Especially since it’s the summertime, there was no way I could conclude this list without mentioning Espadrilles. These are a breezy casual shoe that are perfect for the warm weather.

With plenty of patterning and color options available at a variety of price points, these are the perfect way to complete any casual or semi-casual outfit. These are an especially perfect compliment to a pair of nice shorts: before Espadrilles entered my life, I found pairing shoes with shorts to be a surprisingly challenging task, but these have totally changed that for me.

With these shoes on your feet you’ll be evoking relaxation and comfort while also demonstrating a keen eye for details: just make sure you’re not wearing visible socks.

Ultimately, from the most formal to the most casual looks, having these options in your closet will ensure that you have at least one amazing-looking footwear option for almost any circumstance.

Ready to make your next purchase? Hellman Clothiers has the best selection of meticulously curated European and American brands in Cincinnati: feel free to head into our location in downtown Cincinnati to find the perfect pair of shoes for you.