Top 10 Stylish Men’s Boots Every Grown Man Should Own

Menswear is not only another form of self-expression, but it’s also a vital way to just live your life. It’s what helps you score a first date, get a good job and stay physically fit. This is why it’s so important to create a comprehensive wardrobe that’s trendy, versatile and unique.

And part of growing up is realizing that you just can’t wear the same sneakers to both a birthday party and a wedding. Are you feeling a little guilty about committing this fashion faux pas? Don’t worry – a great place to start is by exploring mens stylish boots that make a great alternative for designer sneakers. 


Why should I invest in men’s stylish boots?

One of the most significant items in any man’s wardrobe is the footwear. Your shoe style can make all the difference in making you look sloppy or put together. Just imagine yourself wearing skinny jeans and a t-shirt. You could pair that outfit with boots, sandals or oxfords and end up with a completely different vibe just depending on the footwear style alone. It can instantly elevate or relax an outfit with a simple shoe change. 

Most importantly, mens stylish boots are just one of those versatile shoes that can work for virtually any occasion – parties, weddings, vacations, holidays, etc. They can be as dressy as oxfords, as cool as high tops, and as casual as sandals. Plus, you can find them in virtually any online trendy men’s clothing or shoe store today like Differio. To make it easier on you, we’ve broken down the most popular boot styles that are fashionable, timeless and practical in any man’s wardrobe.

Here are the top 10 stylish boots for men that want to boost their footwear game:

  • Chukka Boots

Similar to desert boots, British soldiers may have worn mens chukka boots in the past, but today they’re worn by fashion editors, vloggers, influencers and the like. At a quick glance, they look like a cross between oxfords and ankle boots. Essentially, chukka boots are mens ankle boots usually made in genuine or vegan leather with distinctly two or three eyelets laced with skinny ties. Among mens stylish boots, chukkas are definitely a smart-looking shoe that you could wear for work or a causal date. 

Best paired with: business casual clothing

  • Chelsea Boots

If you hate tying your shoes, then you’re going to love the ease of chelsea boots. Although these are definitely a more modern shoe style, they actually originated from the Victorian era and were revived during the 1960s. The chelsea boot is another variation of mens ankle boots without laces and typically fits snug around the ankles with a signature elastic gore. This men’s footwear style is extremely versatile; you can dress it up or down with suits, chinos, leather jackets and jeans. 

Best paired with: smart casual clothing

  • Combat Boots

Combat boots are one of the edgiest footwear styles inspired by military outfits. You can find these casual boots available in a variety of lengths from ankle to knee high. Typically, combat boots for men are designed like mens lace up boots with a speed hook system similar to the silhouette of work boots with a grippy, ridged sole. However, they’re usually made with more fashion-forward details than the average work boot, like studs, fur accents or leather panels. With its sexy army edge, combat boots can easily be paired with leather bomber jackets, olive cargo pants and metal aviator sunglasses.

Best paired with: casual military clothing

  • Sneaker Boots

If you find yourself having difficulty moving on from high-top sneakers, sneaker boots are pretty much the next best thing. A sneakerhead favorite, men’s sneaker boots are the ultimate mash-up of street sneakers and fashion boots that’s so on trend right now. Since they’re a combination of both footwear styles, they’re usually designed like mid-ankle boots with a leather-look upper over a cushiony, sneaker-like sole.  As one of the lightest boots, they’re also ideal for guys that live in warmer climates. You can wear these mens stylish boots with mens streetwear looks, such as graphic hoodies and drop-crotch joggers. 

Best paired with: urban streetwear clothing

  • Work Boots

Although men’s work boots closely resemble military boots (as mentioned previously), these shoes are designed with much more durability in the toe and sole. Keep in mind: they’re designed for construction workers and craftsmen, so they’re going to feel clunkier than mens fashion boots, especially steel toe boots. You can typically find work boots in ankle to mid-ankle lengths with that signature grooved sole for safety grip. If you need stylish mens winter boots, this men’s footwear style also makes a great alternative to traditional fur-lined snow boots. 

Best paired with: everyday casual clothing

  • Oxford Boots

It’s so crucial to have a pair of mens dress boots that you can wear for semi-formal occasions, like business parties, weddings and fine-dining restaurants. This is where oxford boots come in handy, especially if you’re looking for what to wear on a first date coming up. You can also wear brogue boots or derby boots, which are close cousins to the oxford boot. These mens stylish boots are basically dressy oxford loafers designed with a thicker sole and higher ankle to give it that dress-boot silhouette. You can find them in a variety of materials, including leather, suede and canvas.

Best paired with: semi-formal clothing

  • Waterproof Snow Boots

For guys that live in cities with cold climates, men’s snow boots are a must for getting around during inclement weather. You can still look trendy in waterproof snow boots if you know what to look for. Try going for a leather upper with a fitted toe for a style that looks great with skinny-fit pants. You can also find stylish mens winter boots with buckles, shearling and suede accents for a trendier update. Pajar Shoes is one of the few brands of snow boots that hit all the marks across durability, style and comfort. 

Best paired with: trendy winter clothing

  • Motorcycle Boots

You don’t need to own a motorcycle to pull off men’s motorcycle boots. The biker-boot look is edgy, sexy and masculine. You can usually find men’s biker boots with a buckled harness around the ankle in a mid-ankle to mid-calf fit. They’re predominantly constructed in genuine or faux leather in dark shades of black or brown. For the full moto effect, you can wear these mens stylish boots with your favorite leather jacket and distressed jeans. Just avoid wearing these shoes to any formal events. 

Best paired with: moto steampunk clothing

  • Western Boots

When you think of men’s western boots, you’re probably picturing the all-American cowboy boots usually worn with a white crew neck t-shirt and blue jeans. However, there’s so much more to today’s western boots than just the cowboy motif. It’s modernized with a shorter ankle and buckled harness, but still fitted with that traditional short, wooden heel. For a more contemporary look, you can pair western boots with a fringe bomber jacket and ripped jeans.

Best paired with: contemporary boho clothing

  •  Riding Boots

If you don’t already own a pair of mens knee high boots, riding boots are a classic choice that’ll still give your wardrobe some edge. Although it leans on the preppy spectrum, you don’t normally catch a lot of guys pulling off the knee-high look. Riding boots are basically a simple pair of mens leather boots without too much embellishment on a short-heeled sole. To balance the height of these mens stylish boots, you should pair these with slim or skinny chinos or jeans. 

Best paired with: classic preppy clothing 


In conclusion:

There are so many styles of mens casual boots that it’s impossible to list them all, but these stylish boots for men will – without a doubt – give your wardrobe that stylish boost you’re looking for. No matter which style you decide to go with, you’ll find that you can wear them for virtually any occasion. It’s just the start to expanding your horizons across men’s fashion and finding your own personal style. 


Archer Blackhttps://calendly.com/archer-black
I Help Men Attract Health, Wealth, Relationships & Purpose They Want, by Transforming Themselves Into HIGH-QUALITY Men.I'm also amazingly terrible at soccer.