The Best Men’s Dress Boots To Wear This Fall

We've all been there: you put together an A1 outfit for a big night out, but something doesn't look quite right.

Is it the suit? Nope – it's well-tailored.

Shirt? Crisp, white, and well-pressed.

Accessories? Perfectly balanced and color matched.

So what is it? Where's the missing piece of the puzzle?

You guessed it – it's your footwear. The fact is, sometimes dress shoes and sneakers just don't cut it. They sit on two sides of the formality spectrum, so what's a stylish guy to do when the situation calls for smart-casual?

Simple: wear a pair of men's fall dress boots and bridge the gap between formal wear and casual attire.

In today's article, we're breaking out the best styles of men's dress boots and how to wear them this fall.

We'll be covering:

1. How To Style Chelsea Boots
2. How To Wear Wingtip Dress Boots
3. How To Style Ankle Dress Boots
4. Can You Replace Sneakers With Boots?
5. How To Wear Dress Boots With A Suit
6. Can You Wear Boots With A Leather Jacket?
7. Are Dress Boots Business Casual?

Fall Dress Boots Tip #1: How To Style Chelsea Boots

The Chelsea Boot is a British boot that hit the scene in mid 19^th century. Its design is originally credited to Queen Victoria’s shoemaker J. Sparkes–Hall.

Its popularity is largely due to the Beatles, as it was frequently worn by the iconic band. Chelsea boots are close-fitting, ankle-high boots. There is an elastic side panel that allows the wearer’s foot to slide in easily.

Most Chelsea boots have a loop or tab of fabric on the back of the boot that allows you to easily pull the boot up. It’s now a popular boot for the contemporary stylish man.

Pairing Tips:

• Versatile – Can be paired with suits, jeans, or trousers
• The bail of the pant leg should be tapered or narrow as it provides a slimming effect
• Your pants should cover the top of your boot about ½ inch to ¾ of an inch
• There should be no break in the pant leg when worn with trousers, but some break is allowed with jeans
• The fit should be snug but not too tight as the vamp of the shoe is narrow, and you don’t want your toes to crowd and bulge out
• Wear trouser socks instead of thick athletic socks due to the snug fit.
• Sport with pea coats and top coats

Fall Dress Boots Tip #2: How To Wear Wingtip Dress Boots

Wingtip boots are an adaptation of the wingtip brogue oxford shoe. The difference is that the quarter, top-line, and tongue of the wingtip brogue boot are extended just below or slightly past the ankle.

This is a versatile boot. It can be worn with business, casual, and urban looks. There are details such as stitching and perforations on the quarter, the vamp, and the toe of the shoe that aid in the shoe's versatility.

Pairing Tips:

• Versatile – Can be worn with a suit, trousers, denim, and corduroy. Though they are commonly known as dress boots.
• For a more modern dressy look, a wide 2-inch cuff in slim trousers will pull the pant leg down and allow it to drape naturally
• Wear trouser socks with dressier aesthetics and thicker cotton socks with casual looks
• Wear with denim with a cuff or no cuff. The cuffed look is more metropolitan, and no cuff is more conservative
• Wear with top coats and navy jackets

Fall Dress Boots Tip #3: How To Style Ankle Boots

Born out of the Chukka boot worn by British soldiers in Africa in World War II, this style of boot is as about as casual as you can get.

At their inception, they were completely made of leather, but now they can be found in suede as well. They are characterized by thin soles and open lacing with two or three pairs of eyelets.

Ankle boots have calfskin uppers in two parts (each from a single piece of leather; quarters are sewn on top of vamp) and rounded toes.

Common Ankle boots are chukka boots (desert boots) and monk strap boots.

Pairing Tips:

• A more casual dress boot
• Wear with denim, chinos/khakis, or corduroy
• Thicker casual socks can be worn as the vamp is wider and rounded
• Denim slightly above the upper of the boot to show his patterned sock is acceptable.

So how can we use these boots to boost up specific looks?

Fall Dress Boots Tip #4: Can You Replace Sneakers With Boots?

Sneakers are the ultimate casual shoe. They are comfortable and come in an array of different styles. The issue with sneakers is that they are not appropriate for every environment. To be frank, they are sometimes too casual. So what's the workaround? Replace your tennis shoes with boots.

Adding boots to a sneaker look should take the casual outfit to another level. For example, if you are sporting a great pair of jeans and a nice polo this summer, you could add a well-made wingtip boot.

You can also replace the sneakers with Chelsea boots for a more metropolitan and svelte look.

Fall Dress Boots Tip #5: How To Wear Boots With A Suit

You can wear boots with a suit and look great. Remember a suit is a pair of trousers and a jacket that are the same color and made with the same fabric. The type of boot that you pair with the boot typically depends on the type of suit.

Wingtip boots are the go-to boot for this look. The upper of the boot goes past your ankle, providing a classy and sophisticated aesthetic. You want to keep the laces tied tightly all the way to the top as this keeps the boot sleek and well fitting from your toes to your ankle.

Ankle boots work well with cotton summer suits and tweed suits. The ankle boot sits low so that the bail of the pant leg doesn't have to be too high.

Fall Dress Boots Tip #6: Can You Wear Boots With A Leather Jacket?

Few things scream men's style louder than a well-made leather jacket. At some point in our lives, it's reasonable to assume that many guys want to look like bad-ass tough guys.

It's almost a given to wear boots with a leather jacket, but if you want to change it up, don't wear the traditional motorcycle boots or boots with the blue-collar rugged.

I suggest that you add a Chelsea boot if you want to casually dress up the jacket. A wingtip boot with a cuff in the pant leg of the jeans is a great way to add some rugged elegance to your look.

If you're going to be riding a motorcycle, then choose a boot that has a rubber sole. 

Fall Dress Boots Tip #7: Are Dress Boots Business Casual

Business casual is a unique look. It encompasses a bevy of different style options. Whether it's trousers with a button-down shirt or chinos and a polo, boots will take your semi-professional look to another level.

Business casual typically lacks important details such as a necktie/pocket square combination or a french cuff shirt with cuff links. As such, a great pair of wingtip boots adorned with intricate stitching or a boot with a buckle will spice things up.

Since business casual usually lacks the details of a necktie/pocket square combination, a great pair of wingtips with details or ankle boots with a buckle will supply some subtle details that will stand out.