We all love a stylish pair of Oxfords, but sometimes the occasion calls for something a little less formal every now and again. Of course, I'm talking about footwear that has a more casual shoe style.
Note the word casual – not sloppy. Those worn-out, dirty old tennis shoes aren't going to cut it!
But with so many casual men's shoe styles out there, it's easy to get overwhelmed. So in this article, we give you the best casual men's shoes for fall and winter!
- 10. Canvas Sneakers
- 9. Bluchers & Derbies
- 8. Dress Sneakers
- 7. The American Combat Boot
- 6. Men's Loafers
- 5. Moccasin-Style Boots
- 4. Chukka Boots
- 3. Double Monk Straps
- 2. Chelsea Boots
- 1. Brogues
Men's Casual Shoe Styles #10. Canvas Sneakers
Sneakers have a turbulent past. They started life as the staple of peasants in the 18th century.
When the U.S. Rubber Company started producing rubber-soled shoes with a canvas top (called Keds), they started creeping into the mainstream. Keds are considered the world's first REAL sneakers.
Why are they called sneakers? Rubber soles produced little-to-no noise, which meant the wearers were “sneaky.” Yeah, it's not the most breathtaking origin story.
When it comes to men's casual shoes, sneakers are as casual as you can get. They will never replace a solid pair of dress shoes, but you can count on them for comfort in the most laid back of occasions.
Need specifics? I got you covered.
- Basic sneakers include brands such as Converse and Vans. For the most part, they come in canvas bearing more basic colors. They're affordable and simple – a great way to start.
- Luxury Sneakers are considerably more expensive. They come from top brands like Tom Ford and often sport more than just canvas. Expect some leather thrown in for good measure.
- Sports Sneakers like those made by Nike and Adidas are designed for functionality and sports. If possible, stick to that – don't make a habit of wearing them out.
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Men's Casual Shoe Styles #9. Bluchers & Derbies
They look the same at a glance, but there's a key difference between a Blucher and a Derby.
They both have open lacing, but the Derby features large quarters with eyelets. Bluchers' uppers are one whole cut.
Bluchers have a fascinating history that dates back to the Napoleonic Wars. Following numerous defeats at the hands of France's Grande Armée, Prussian Field Marshall Gebhard Leberecht von Blücher was forced to reconsider Prussian army boots.
The new designs were supposed to keep up with their French counterparts. Considering that it was Blücher who delivered the killing blow to Napoleon at Waterloo, maybe it worked!
Bluchers and derbies are a healthy middle ground. They're more formal than Monk Straps but less so than classic Oxfords. This makes them useful to dress up without going too far.
Men's Casual Shoe Styles #8. Dress Sneakers
Dress Sneakers make powerful additions to any man's closet.
What sets Dress Sneakers apart from regular sneakers? They're often topped with leather or suede instead of canvas – and use features taken from traditional Dress Shoes.
You can find Men's Dress Sneakers with broguing detail or with monk straps. It's this blend of two distinct shoe styles to create something truly distinctive.
Men's Casual Shoe Styles #7. American Combat Boots
The modern American Combat Boot took some time to get here. The very first standardized boots the “Jefferson boots” were introduced in 1816, without a right or left shoe (imagine fighting in THAT).
It was after the Civil War that we started to see left and right boots and even then they only came in four sizes. If you didn't fit the bill, you had to pay for a custom pair.
By 1918, we started to see laced boots at last. The largest transformation came in 1941, with the paratrooper boot. They received additional support on the heels for jump landings.
Combat boots are largely a casual addition to many outfits. They can be paired with dressier looks if the leather is sleek enough. Overall, however, they'll look badass with the Marlon Brando look – a white t-shirt and blue jeans.
Men's Casual Shoe Styles #6. Loafers
If you want a fantastic shoe for the heat, look no further than the classic men's Loafer. Its origin stems from Norwegian peasant slippers, which business owner George Henry Bass used as his inspiration.
In 1936, the Bass Weejuns were released, and they were soon dubbed as Loafers.
Several variations of the Loafer emerged in the years following, and you can learn all about them by checking my ultimate guide to men's loafers.
Additionally, they make superb additions in Fall because of how they expose your ankle – granting additional breathing room. I recommend using no-show socks to maximize their comfort.
Men's Casual Shoe Styles #5. Moccasin-Toe Boots
What is a Moccasin? Well, it's a collective term for all Native American shoe styles. They vary intensely by region, but one aspect which stood out was the separate piece of leather sewn over the tip to forge a flattened look.
Boots that take inspiration from this are excellent tools to round out a casual wardrobe. They are a fundamentally casual tool, though. Don't attempt to pair them with your more elegant menswear.
Men's Casual Shoe Styles #4. Chukka Boots
When it comes to men's casual shoes, the Chukka boot has both military and sporting heritage.
They originated in India where British colonial officers played Polo with the famous boot. The term “chukkar” even comes from the Hindi term “circle” which can be translated to “casual.”
The Duke of Windsor debuted them in the USA when he wore them on a state visit in 1924. Following that, they became the standard boot for British troops in the deserts that faced off against Rommel's troops.
As a result, chukkas serve as an effective middle ground between dress shoes and sneakers – not too different than the blucher.
Men's Casual Shoe Styles #3. Double Monk Straps
As the name suggests, this shoe has very holy origins. They were developed by monks as work shoes in the Medieval ages. The buckle kept them secure while they worked the fields outside abbeys.
The formality behind a Monk Strap is a hot debate among menswear enthusiasts. It really falls down to regionality.
A simple black Monk Strap is considered suitable for formal attire in England. Thusly it's up to your judgment. Just remember the basic rule – the darker the shoes, the more formal.
Men's Casual Shoe Styles #2. Chelsea Boots
Few boots really drive home sleek and casual perfection the way Chelsea Boots do. The Chelsea Boot Company started producing them under the leadership of J. Sparkes-Hall. The company designed them for Queen Victoria herself.
The boots were first used as riding boots, the elastic on the sides making them easy to slip on and off.
They make amazing casual boots that really lend a much-needed elegance to any man's outfit. The Chelsea Boots is a must-have in a Fall closet.
Men's Casual Shoe Styles #1. Brogues
Now, let's get one thing straight. Brogues aren't a specific kind of shoe. Indeed, you can find brogues on most of the shoes we've discussed.
They're a pattern.
Specifically, they are a series of decorative perforations that are all over the shoe's leather. They originated in Scotland, where shoes had holes punched in to allow for comfortable passage along the region's many swamps.
You'll find Brogues in quarter (along the toe caps seem), half (on the toe cap), and full (all over the top of the shoe) variations.
Though it isn't formal accouterment, it is absolutely classic. Every man should have at least one pair of Brogues in his closet.
If your outfit doesn't suit the season, you won't look your best, and that goes double for your choice of shoes.
Either way, you can't go wrong with any of these choices. Just make sure you keep them clean and fresh! Check out my guide on how to stop shoe stench for good.
Click below to watch the video – Wear Boots With Jeans & Look Amazing