My 5 Favorite Ways to Style Red Wings

Thanks to Humphrey Tsui for supplying a bunch of these photos.

Red Wing Shoe Company started in 1905 to outfit workers in industries like mining and metalworking with quality boots that would protect them at work.

Now, more than 100 years later, work boot technology has evolved to include Gore-Tex and carbon fiber — and Red Wing sells such state-of-the-art work boots. Wisely, though, they’ve preserved the old fashioned boots that countless people love to wear casually.

Red Wing Heritage boots still have qualities that come in handy on jobsites: water resistance, longevity, and a level of stability that makes them more comfortable after a long day on your feet when compared to squishy sneakers.

But those are all qualities that are useful for regular guys as well, and these boots look so dang good that anyone can pull them off — if you know how to style them correctly.

Below, I’ve compiled six ideas that’ll work with with either of their most iconic boots: the Iron Ranger or the Classic Moc.

1) Chinos and a T-Shirt

There’s nothing more basic or approachable than a pair of chinos (or khaki colored fatigues) and a simple T-shirt, which I’m certain most guys own.

While chinos are much easier to dress up than jeans, they can be worn just as casually — after all, they originated as military workwear.

Both the vintage-leaning Iron Ranger and the modern-leaning Classic Moc elevate these closet staples by introducing a classic heritage style element.

The Iron Ranger will give you a bit more of a vintage Americana look while the Classic Mocs, with their contrasting sole and more versatile aesthetic, lend a more modern take on the casual leather boot.

You might think chinos and a T-shirt isn’t much, but imagine wearing the same fit with a basic pair of running shoes, and you’ll understand the impact the boots will have on the overall look.

Chinos are pretty basic because they pair with anything — that’s why it’s the quality of your footwear that will signal how thoughtfully you’re dressing.

2) Chore Coats

Maybe the most versatile jacket a guy can own, a chore coat (or chore jacket) can complement just about any kind of outfit and any kind of Red Wing boot.

These coats work especially well because they are cut straight, work with most body types, and have loads of pockets. They’re neutral but also refer back to the workwear origins of the boots you’re pairing them with.

(Chore coats aren’t hard to dress up to smart casual office wear either, but since I don’t think these boots can be worn that formally, I’m not touching on the office kind of “workwear.”)

Wear them with a T-shirt, sweatshirt, or collared shirt like an Oxford cloth button down underneath, but keep it all casual (no dress shirts, please).

Jeans or chinos both work well with chore coats — in fact, a chore coat gives you a good opportunity to wear both at once: a denim shirt with chinos is a great look.

3) Denim

Denim is obviously a no brainer, which is why I waited until the third entry to bring it up. I’m subverting your expectations!

But denim jeans are as American as Red Wing themselves — Levi Strauss himself did patent them here in the U.S. in the late 19th century. Red Wing boots and jeans share not only a workwear history, but a history of Americana itself.

A couple of things to bear in mind when putting together a denim-and-boots look: the less ‘beat up’ your denim is, the more you’ll look both put together and relaxed — as in, you won’t look like you’re trying too hard.

Also, opt for a straight leg or regular cut. The skinnier your jeans are, the more outsized your chunky boots will look. Skinny jeans can work great with other boots, but not with Red Wings.

Keep it simple with a T-shirt or a henley and top it off with something “casual Americana” but not over the top, like a trucker jacket or a buffalo plaid overshirt.

4) Chambray Shirts

Chambray shirts are one of the most versatile casual shirts you can own. Perfectly straddling “smart” and “casual,” they pair effortlessly with chinos, fatigues, or denim.

Any Red Wing boots can work great in this context. The Iron Rangers will give you a bit more polish while the Classic Mocs will reinforce the workwear nature of your shirt.

In terms of color you can’t go wrong with muted neutrals. Navy, light blue, khaki, and olive are a can’t miss against your boots no matter what combination you go with.

To avoid looking flat or monochromatic, however, make sure there’s a bit of contrast with at least one of the items you put on.

5) Leather Jackets

Leather jackets of all varieties work really well with these heritage boots because they’re designed to age and patina in a similar way. They’re also situated in about the same area of casual but high quality Americana.

Think about the scratches and scuffs you’d develop on both — both a leather jacket and quality boots become part of your story and reflect the journeys they’ve shared with you.

Nick’s Cafe Racer from Schott NYC (above) looks especially smart with the Iron Rangers because of their matching color and texture.

Something like these sheepskin shearling jackets that Humphrey’s wearing with his brother, above, can be another great option. Like the Classic Mocs, it’s rugged, textured, and gives off a strong sense of its construction.

6) Vintage Military

American workwear and military clothing have always overlapped because of their shared vocabulary of utility and durability.

So pairing Red Wings with something like a surplus M65, deck jacket, or fatigues makes a lot of visual sense — both convey a sense of authenticity and function.

The Iron Rangers will also work great with a piece of military surplus — it will look a little less workwear oriented and read more vintage.

Olive green looks great against brown leather, but try to limit yourself to a single piece of surplus. Wearing any more will push you into military cosplay territory.

What Won’t Work With Red Wings

There’s no question the Iron Rangers and Classic Mocs live in the more casual style space — these shoes have a workwear/labor origin. And that means that the opposite — formal and prim — won’t provide that visual consistency.

You don’t want to wear either of these boots with suits, for example, or Italian tailoring. The divide in the contrast of styles is just too wide. So whichever style you lean toward, keep it casual.

The other thing to keep in mind is that these are large, robust shoes with lots of toe space. They’re not slim, nor are they minimal and streamlined. It’s therefore reasonable that they’ll look strange against skinny pants or slim silhouettes.

These are classic styles that haven’t changed for decades, so pairing them with trendy skinny silhouettes is an automatic mismatch. Keep the leg of your pants regular or slightly wide. (Personally, I look for a leg opening of at least eight inches.)

In the same vein, the boots are chunky and look pretty substantial, not light and flowy. So wearing them with fabrics that are loose and breezy — like linen trousers — or items that have much less presence — like shorts — can look odd and draw attention in the wrong way.

Beyond Heritage

Beyond the Iron Rangers and classic Mocs, Red Wing Heritage offers a wide range of styles that can easily slot into most wardrobes.

Minimal silhouettes like those of the Classic Chelsea and Weekender Chukkas are great solutions for guys who want to keep it simple, while other boot options like the Blacksmith, Engineer or Logger can offer alternative-but-still-rugged profiles, so it’s well worth checking out what the full Heritage line has to offer.