Staple #17: The Casual Boots

Improving your casual style is just as important as your formal wardrobe. Most men will still default to a casual attire unless they have a reason to dress up. Unfortunately there’s some weird law of physics that stipulates the days when you look your worst are the days when you meet the most important people. I’ve come up with a decent workaround though – dress stylishly even when you dress down.

For much of the US this time of year means cold weather, rain, and snow. While there’s always the idiot out shoveling his driveway in shorts, most of us know that seasonal dressing is appropriate both in form and function. In the past I’ve covered a good-looking way to keep your upper half warm and today we’ll look at a casually stylish option for your feet.


Known as work boots or casual boots, these are too bulky and rugged to look good with a suit. However, they can be worn in casual, work-related situations; going out on the prowl with your friends; or even as a good High/Low option for something business casual like family Christmas pictures.

The boots featured in this post are from Cat – the ubiquitous workwear company. They have released a new collection of simple footwear that is built to withstand the abuse a working man can throw at them and were kind enough to offer me a pair of their Orson boots. A lot of the choices are a bit too steampunk for my tastes but they have a couple of simple shoes and boots that would be a great option for your informal style. They also come in at a price point that is more palatable for the men who don’t want to shell out $300+ for a pair of Wolverine’s or Red Wings.


swinging baby

Shoes are an excellent way to provide some contrast with your High/Low style. If you have on a pair of jeans and a henley you can dress it up with some loafers or dress shoes. If you’re wearing dress slacks, a blazer and a button-up, then some work boots will dress it down a bit.

boots and tweed

The key to pulling off dress boots as part of a High/Low look is to wear them with clothing in casual cuts or made from more rugged materials. By pairing them with tweed dress pants – a fabric that was originally used for hunting in England, and a casual navy jacket with patch pockets and notch lapels the boots are congruent with the rest of the outfit. If I had them on with a formal suit and a tie the contrast between high and low would be too strong.


There’s a reason these are also called work boots, they’re made to be worn in tough situations. My first time wearing this pair was out pheasant hunting with my in-laws on Thanksgiving. The desert terrain of Utah isn’t exactly friendly and I knew it was a perfect opportunity to test the “work” of these boots. You want to look for a quality leather construction in the uppers and a high enough vamp that they’ll cover your ankles. This will provide extra protection from snow, mud, underbrush, or even ankle-biting animals. They’re not bulletproof, but any additional protection is always nice to have.

garage door opening

While you’ll still want to shine these up as a way to take care of them, work boots don’t have to look pretty. The scuffs and scratches give them character and these are ideal footwear for Saturday morning chores, helping a buddy move, or a weekend at the cabin.

Going Out

night out

There’s a certain masculinity that is communicated with a pair of work boots. They indicate to people that you’re not afraid of manual labor and putting yourself in situations that mean you can and will get dirty. By having your boots on with some dark jeans, a peacoat, and a casual shirt (in a dark color) you’re ready for a night out with your buddies. That may be seeing your favorite band, trolling dive bars, or just seeing where the night takes you. Have a simple, streamlined outfit on when you don’t have anywhere fancy to be gives your presence an element of danger that will spark people’s curiosity.

The Orson boots though fall into a great compromise between quality and price. I can definitely recommend them for a man who wants a good, unique pair of boots that isn’t going to break the bank. If you’re interested in picking them up, you can do so through Amazon
and Nordstrom.

PS. I’m having a holiday sale. You can get a Basic Consultation for only $15 and that $15 applies to new clients pursuing Event or Online Consultations as well.

NORDSTROM - Shop Men's Denim

Meet The Author

Tanner is the founder and primary author of Masculine Style. He lives in Salt Lake City, Utah with his wife and two kids, and helps run Beckett & Robb - a men's clothing company built around custom suits and shirts.


Carl Sagan

Ordered my first pair of casual boots last week.

Can’t wait to get them


Few years back, rediscovered some old scouting boots in the closet. They still fit then and became my day to day shoe. They’ve since been relegated to ‘lawn mowin’ boots, but I’ve got some dark brown timberlands to take their place.
After a while, sneakers start to feel like ballet shoes in comparison, and look dumb in any non-athletic activity.


There’s definitely room for sneakers in a warmer environment, but once the weather starts to turn boots are the way to go.


Quick question,

What are your views on brogue boots? These seem quite fashionable atm, but Im on the fence. I didn’t like them, but I saw a really nice pair the other day.

Love the family pic!

Seth McKnight

Tanner, where did you get the grey pants you’re wearing in the first three pictures?

Comments are closed.