The Everything Guide to Dress Boots

Just a few years ago the very idea of dress boots would have seemed out of place, if not outright weird. Not anymore.

I remember going to church when I was a kid and wearing a pair of black boots with my slacks because I couldn’t find my dress shoes. At the time my mother was furious with me but I couldn’t help to think they looked WAY better than my boring oxfords.

Apparently, that viewpoint is now very much accepted in the fashion community. And with that said, it’s come to our attention that every gentleman should know when to wear, how to wear and to what to wear dress boots with.

Especially because it becomes obvious this fashion trend that began at the end of the Victorian era is not a trend at all, but a style staple that’s here to stay.

What Exactly are Dress Boots?

Good question. Dress boots are distinctly different from outdoor boots in a few ways. One way is that they are not as readily made to be used outdoors. The best dress boot is actually a dress shoe with an extended upper portion to cover the ankles. They are made in a very similar way to dress shoes.

The style is more based on an oxford, and though they are usually made of leather, the upper portion is usually softer than a traditional boot. dress boots, dress boots for men, mens boots,

When is the best time to wear them?

The best way we could answer that to say that unless there’s a funeral or wedding, anytime is the best time. And in this case a wedding or funeral may be appropriate. The dress boot gives you the option to be incredibly versatile in your choice of style. It can dress up a casual look of jeans and a blazer, or it can give a smart looking suit the spark it needs.

It’s up to you gentlemen. Just make sure they’re well taken care of and don’t look as beat up as the boots you used for your Sunday hike with the boys.

What do I Wear Dress Boots With?

As was surmised in the last paragraph, you have the option of wearing dress boots in almost any way imaginable. The only thing we would recommend against is the use of baggy pants or jeans. You want the boot to be seen. And because they are dress boots, we would also recommend not going too casual while wearing them. Here are a few examples of the best way to wear the famous dress boot:

How to Wear Dress Boots

There are 3 definite ways that are, preferable when wearing dress boots or boots of any kind really.

1. Cuffed

As you can see in the middle picture, the young gentleman has his jeans cuffed so that the top of the shoe is more visible when standing up. The whole point of wearing a dress boot instead of a dress shoe is that there is more shoe to see. The key to this look is to wear slim fit jeans long enough that you only have to cuff them two times at most. Otherwise, the cuffed jeans look baggy and disorderly.

2. Pants tucked inside

The right-hand picture show dress boots that have the pants tucked inside. The way to do this is to make sure the tops of the boots are loose and a little open so that your pants (again slim fit) will easily slide inside. The best looking boot for this look tends to bend towards the more rugged side.

By the way, we don’t recommend lacing or zipping the shoes all the way up if you have your pants tucked inside, you might run the risk of looking like a jinni, especially if your pants are loose-fitting at all.

3. The  Half break or Full Break

The last picture on the left is an example of how you can wear a nice dress boot partially covered up. The pants in this image show a full break with the shoe. This means that the ends of the pants don’t actually rest on the curve of the shoe. It’s a slight form of the old school term “flooding” but highly acceptable when wearing dress boots. If you want more coverage and don’t want your socks to show so much when you sit, you can opt for a half break, which allows the pants to rest on about  1/2 the shoe.

The best way to go with a full break is to wear cuffed pants, and straight pants on a half break.


Gordon Rush Styles Men’s Boot

Wingtip leather lace-up with a rubber sole and cleated on the outside. This boot is a classic addition to your overall wardrobe. Its style is perfect for cuffed jeans or a slim fit gray pinstriped suit.

Because it can pretty much go with anything in your closet, and make anything you own look even better, this is a must-have staple of every stylish gentleman.

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 100% Leather. Rubber sole, wingtip brogue and even though it’s a bit more expensive it will last for years to come.

High-quality boots that are rugged enough for a trip in the woods and nice enough to wear with your favorite sports blazer.


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Ferra Aldo Polar Brown Lace Up

Remember the boots with the pants tucked inside? Here’s a great option to try when going for that look. These are 100% leather, great quality, and the price is great.

The other great thing about these dress boots is that you can lace than all the way up and use the half break or full break for a nice clean classy look.

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Now you have everything you need to expand your wardrobe. The whole idea behind dress boots is to have fun. Buy a pair that will last a long time and use them however you please.

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