Styling Sneakers in the Winter the Right Way

We live in a society that is continually getting more and more casual. Suits are giving way to a more business casual aesthetic. Dress shoes are being kicked off and shoved to the back of the closet in exchange for boots and sneakers. 

The gum-soled staples of the stylish man have been around for a century and a half and are more stylish than ever and are now moving front and center in every man’s closet. 

That doesn’t mean we can simply stop caring about how we look regularly and just throw them on without thought. This isn’t the time to start succumbing to the increasing desire to adopt the dad look with lawn-mowing sneakers.

Instead, this is a time for you to look at the sneaker market and pick out the ones that best serve you so you can find that bridge between comfort and fashion. Wear the sneakers. But do it in the right way.

Sneaker Style For The Modern Man

Way back in the early 1800s, it was mostly a choice between work boots and dress shoes for men everywhere. If you worked in the fields or drove cattle, cowboy boots, and work boots were the choice. Something comfortable and rugged kept your feet warm and dry.

If you worked in the city or were going out on the town, then dress shoes were the go-to footwear. They were about style over all else. However, the continuing interest in athletics caused the adaptation of the sneaker—the perfect combination of both shoe styles. 

By the middle of the 20th Century, sneakers became much more prominent thanks to the explosion of popular professional sports. The Converse All-Star became one of the most famous shoes of all time and eventually a staple in every sneaker head’s closet. 

While people spent the last century telling us that the sneaker was only appropriate for athletics and ultra-casual wear, we have adopted the soft-soled icons into every facet of our lives.

From being related to running a mile or mowing the lawn to dressing down a suit or being the centerpiece of a causal outfit, sneakers became a commodity in so many wardrobes. 

There are numerous types and styles of sneakers, all with their own design intent. Knowing the design intent will help you figure out how to make them work for you. And the way you can wear them effectively in any situation. 

White Sneakers 

The white sneaker is the most important among the long list of sneakers you will run into (pun intended). It will be the most versatile shoe in your wardrobe. It can be worn with shorts, jeans, chinos, and vibrant or dark colors. 

When I say white sneakers, I don’t mean athletic tennis shoes. These are different from the basic New Balance your father wore when mowing the lawn. These are low-profile, thin-soled shoes that don’t look like they belong in the gym. They should have minimal detailing as edges collect dirt and grime. Keeping them clean will be step one always to look stylish.  

Some of the best looks to wear the basic white sneakers with will be blackout looks or bright colors. The bright colors will look great in the summer. Wearing black jeans, a black sweater, and a black wool peacoat with your white sneakers is the perfect winter look. You get bonus points if you have a white watch and white ball cap to keep the look balanced. 

Dress Sneakers

It was only a matter of time before the rapidly disappearing formal style caused the dress shoe to change. While dress shoes may be essential for your suit in many formal situations, dress sneakers are a great substitution. 

Many of these shoes are a combination of two types of shoes. You are sporting a dress shoe upper like a brogue or an oxford and a sole like a Nike sneaker. While these will be the most common dress sneakers you will find on the market, they aren’t the only ones. You will also find other low-profile leather sneakers in standard dress shoe colors. Dark and light brown or black will be essential to your closet. 

The best way to wear these sneakers in the winter will be to pair them with your winter suits like wool, cashmere, or tweed. They will look best when wearing them just like you would a pair of dress shoes.

This means you can also throw these on with your dark dress denim for a tremendously elevated casual look. Throw on a heavy winter sports coat to complete the style. 

Iconic Sneakers

Iconic sneakers are those specific brands or models that stand out due to their status in our collective sneaker hierarchy of adoration. These are those shoes that we have seen on T.V. and in magazines and made famous by your favorite athletes, actors, and musicians over the years. 

The shoes falling under this category include the Converse Chuck Taylor. They were born on the basketball court and became the number one for guys like Dr. J. But since have become the most iconic Converse ever. They also include the P.F. Flyer, the same shoe Benny “The Jet” Rodriguez wore to best the Beast in The Sandlot.

Finally, the third most common icon is the Adidas Shell Toe. Rising to prominence in 90s hip-hop, they now are experiencing a resurgence. 

Wearing these shoes in the winter comes down to featuring them in the outfit. While these shoes are sometimes primary colors, they have notable details that make them unmistakable.

The iconic sneakers’ winter wear mainly includes jeans or chinos with sweaters or button-ups. If you want to show off your icons, your pants should be rolled up to feature those notable details. The bomber jacket is always the best coat to wear with your icons. Casual, cool, and just as iconic as the shoes you wear with it. 

High Tops

The Converse Chuck Taylor was the high-top that started it all with sneakers protecting the ankle on the basketball court. But while that is the iconic beginning, the Air Jordan line is the King of the Hill. The high-top sneaker is one of the most famous casual shoes of the last forty years, and it is only getting more famous. 

The Air Jordan line made wearing basketball shoes as a casual look with denim and graphic tees cool. The bright colors of these shoes give you a framework to work with in coordinating your look.

Much like the icons, these shoes are the feature of an outfit. They will be thicker than most other shoes you have on and will look great with joggers. Shorter pants won’t interfere with your attractive shoes. 

As far as the coats that will look best with these kicks, the denim jacket is going to look great, and the multitude of colors on your feet make it harder to find a coat that can complement it. The basic denim color is a blank slate of color, making it the perfect partner in crime for your Air Jordans, Allen Iverson’s The Question, or Kobe A.D.

Low Tops

Just like your white sneakers, low tops are some of the most versatile in your closet. While the white sneakers are meant to be as basic as possible, these are a little more fun. They will have bright colors and details like brand insignia that keep these at the top of the style game. 

Some of the other sneaker types will be low-cut, and the rules should follow those listed. For your basic low-top, the idea is to have fun and wear them with almost anything. Jeans and chinos will look the best in ultra-casual moments. But if you are feeling like you want to play something differently, a good, unstructured sports coat will never steer you wrong. 

What Pants Can You Wear With Sneakers 

Virtually all pants will look great with sneakers if you do it right. Jeans are the ultimate in casual wear and can be worn with any of the above selections. However, high-tops and icons are the most suitable. 

Chinos are a solid step up from jeans, so they shouldn’t lean one way or the other. But low-tops are the middle-of-the-road choice for those. 

Finally, if you are wearing dress pants, suit pants, or other more elevated selections, go for the white sneakers or the dress sneakers. The elevated looks of both will go nicely.  

The temperature drops, the wind blows, and the snow piles up around the country. Winter brings with it a lot of downsides, but that doesn’t mean that your style has to suffer. 

Sneakers are some of the most stylish items in your closet and do a great job of showing off your personality. Expressing yourself through the selections you make has never been easier. 

While it may seem confusing or overwhelming when shopping for sneakers, this handy guide not only breaks all sneakers down into a handful of styles but also how and what to wear with them. Stay warm, stay stylish, and have fun this winter.