Dress Boots

A friend of mine asked me to explain what I consider to be “dress boots.” These are boots that go well with suits and dress clothes worn to work in an office, to church, or for dressy social occasions.

Many men search for information on whether or not they should wear boots with dress clothes. I am a firm believer in doing that, and I do every day. I do not own any dress shoes, so when the occasion calls for dressing up for meetings with The Big Cheese or to attend a wedding, church service, or a formal event, here are some descriptions and suggestions for men’s dress boots.

“Dress Boots” fall into four major categories:

1. Dress shoe-looking short boots

Testonicognac1This style of “boot” is about six to seven (15 to 18cm) inches tall. Some long-standing, well-regarded manufacturers of men’s dress shoes such as Alden, Allen Edmonds, Cole Haan, Testoni, To Boot New York, and others make “tall shoes” — that’s about how I describe it. The vamp (foot) looks identical to their dress shoes, but then they have leather shafts that go up about the ankle.

These bootettes (my own concocted word) can be worn by a man who feels that he must wear dress shoes. There are some men who will not wear anything like a cowboy boot, so these formal dressy short boots will get him into a boot yet let him feel and look like he is wearing the finest dress brogues or wingtips.

DressblacksuitI admit, I have some pairs of boots like these. I like how they look, but am careful not to ruin my reputation of being a true Bootman by wearing them too often.

I wear these boots most often when I have to go to places with magnetometers (some call a metal detector), and when I am with a group of big cheeses. Example: Congressional Office Buildings in DC. I don’t want a delay of having to be wanded or remove a pair of taller cowboy boots, have them run through an X-ray while The Boss and The Boss’ Boss watch me get myself back together. These short boots don’t set off the alarms and I can walk right through and be on my way.

If considering dress-shoe-looking short boots, be very careful not to be fooled by a designer name and find the COOL (Country of Origin Label) indicating China, Thailand, Indonesia, or Pakistan as the location of manufacture. Labels like Georgio Brutini and Florsheim are examples of boots to avoid. The cost is low but the quality is poor.

2. Dress leather cowboy boots with rounded toes

RoperfootThe feature of cowboy boots that often strike fear of “what will other people say?” in the hearts of timid men is a pointed toe. But not all cowboy boots have pointed toes. In fact, these days, the most predominant style is a square or blunt toe.

The other feature of cowboy boots that strikes fear among the timid are the heels — too tall (in some men’s opinions) or too loud (they don’t like to be noticed for a distinctive-sounding “boot clunk.”

Lucroperblack10The most common rounded-toe cowboy boot with a low soundless heel is a roper style boot. These boots are short (usually 10 inches/25.4cm). When made of black, brown, or black cherry leather, they have a very subdued appearance and do not attract attention that the timid are afraid of.

But not all men who wear ropers are timid. Roper boots are inexpensive and are worn by a lot of men in the midwest, south, and southwestern U.S. states. Ropers are much more common on men than dress shoes.

These boots are solid, comfortable, affordable, and probably the most common cowboy boot out there. They are worn on all occasions from dress-up to dress-down. I have several pair and wear them from time to time, such as to the office.

Like cautioned above — be very weary of the COOL and don’t end up with boots made in China. Unfortunately, some major commercial U.S.-based bootmakers outsource some of their cheaper boots to China, such as Justin boots. Generally, if the price of a new pair of ropers is less than U.S. $150 MSRP, look closely for information on where the boots are made. Some retailers hide that information on their website and use words like “imported.”

3. Traditional leather cowboy boots

Lucmidbrownfr09Traditional cowboy boots are 13 inches (33cm) tall and usually have a heel height of 1.25 to 1.50 inches (3.2 to 3.8cm). It is quite possible to find these boots with a french toe (subdued square), blunt toe (narrow square), or square toe — so if you’re afraid of “pointy-toe cowboy boots” not being acceptable, then there are alternatives.

Good quality traditional cowboy boots shine well and look GREAT with suits (jacket & tie), dress clothes, or khakis at the office. Walking on carpet or other soft flooring doesn’t make the heels cause a sound to attract attention. Now, admittedly, walking with traditional cowboy boot heels across wood floors will definitely produce that distinctive “cowboy boot clunk.”

You know what? Some men, including me, LIKE to hear that sound. The boots contribute to a masculine style of a confident man.

It is possible to find dress leather boots in all colors, but those that fall into the “dress cowboy boot” category are usually black, brown, or black cherry. I have about 15 pairs of traditional leather cowboy boots in these colors.

4. Traditional exotic-skin cowboy boots

Lucbccroc11blogNothin’ says “fancy-dress-up” more than a pair of quality exotic skin cowboy boots. Boots made with the skins of crocodile, alligator, or caiman, lizard, and ostrich are much more common (and affordable) these days. And man, do they look sharp with dress clothes!

I have several pairs of cowboy boots made with exotic skins that I wear very regularly to the office. In fact, exotic skin cowboy boots are the most plentiful in my cowboy boot collection.

LandonsuitWhy? They look great and contribute to a style of class, masculinity, and confidence that I am known for. I see men around the office check out my boots daily and I can tell they admire the boots and/or my courage to wear them. But hardly anyone says anything about them because boots like these are sorta my signature when I am not riding my Harley.

It is quite possible to get exotic skin boots in a wide variety of colors from white to bone to tan to blue to red to green to orange (cognac) — you name it; they can dye it. However, for dressy occasions (especially when a man wears them with suits), boots that are dyed black, black cherry, and brown are most common. Also, boots with fancy inlays and stitching patterns are usually best when worn with denim jeans in a casual setting.

However, being the boot aficionado that I am, I wear boots with fancy designs as often as I wear more subdued-looking boots. I am long past worrying about “what will so-and-so say?” I am my own man — confident in boots.


So these are my opinions about dress boots. I am not a style queen blogger. I am a guy who enjoys his boots and wears them every day!

Life is short: wear boots. (Learn how, here.)

2 thoughts on “Dress Boots

  1. Agreed! Nice dress boots really dress up khakis like no other shoe. I’ve always had great comments, though I did feel a little like a lost Texas oil baron wearing teju lizard up here in Canada. But otherwise, boots for every occasion nowadays.

Comments are closed.