The Right and Wrong Way to Style Red Wing Iron Rangers (5 fits + 5 mistakes)

So, you’ve got your pair or you’re thinking about getting a pair of Iron Rangers, the classic American work boot that has been elevated beyond the jobsite into becoming an indelible icon of casual style.

Now you’re eager to get that patina patina-ing, but wait! Although these bad boys are pretty versatile, you might be unsure where to start when it comes to how to wear Iron Rangers. To help you out, we’re giving you some simple templates to help you come up with ideas — and finishing with common mistakes you might want to avoid.

The goal here isn’t to tell you to buy the exact brands and models Nick is wearing (although I list them all with links). It’s more to give you ideas and templates for some inspiration.

1. Americana: Waxed Canvas Jacket and Jeans

• Jacket: Flint & Tinder – Waxed Trucker Jacket
• Shirt: Buck Mason – Field-Spec Heavy Tee
• Pants: Left Field NYC – Wide-leg Smokestacks on left, straight leg Greaser on right
• Hat: CAT Workwear – Original 1904 Cap

First up is the classic Americana fit: a waxed trucker jacket with jeans. These jeans are some of our favorites, made by Left Field NYC, shown here in two different cuts: the wider Smokestacks (left), and the straight leg Greaser (right). The Smokestacks are the widest jeans they offer, and since the Iron Ranger is a pretty bulky boot, we think this is the best fit for these boots.

The Iron Ranger is pure Americana and you could wear it with a super British waxed jacket like a Barbour, but there’s no escaping that the best way to wear this classic work boot is with the classic work fabrics denim and canvas. They’re both dense cotton weaves that originated as blue-collar apparel and gradually became widespread as regular casual clothes for everyone — pretty much the same journey the Iron Ranger took from workwear to casual wear. Because who doesn’t want their clothes and footwear to be durable, whether you’re bricklaying or not?

2. Uno Reverse: Denim Jacket and Canvas Pants

• Jacket: Tanuki – TNK402ID Type 2
• Flannel: Thursday Boot Co – Summit Flannel
• Pants: Grown & Sewn – Foundation Pant

For the next outfit, I’m going to flip the fabrics so we’ve got denim up top and canvas on the bottom.

Canvas pants are super underrated and they’re the best pants to wear with a denim jacket: they’re both hardy cotton but denim’s a twill weave and canvas is a plain weave, so you’re not doubling up on fabrics. (Nothing against fans of the Canadian tuxedo, though!) These are from the Brooklyn brand Grown & Sewn, who pigment dye their canvas pants so they fade more like jeans.

The denim jacket here is from Japan’s Tanuki. I love it because it doesn’t have the usual tonal stitching you get on a jean jacket, but alas, this model was a limited edition. You can just get a regular denim jacket! While mine’s a Type 2, I think Type 3s are the most flattering.

Lastly I tossed on a nice heavy flannel underneath; this one’s from Thursday Boot Company. I’m a big fan of how this outfit comes together because it’s all casual Americana and all durable cotton, but you’re not doubling up on any of the fabrics.

3. With a Chore Coat and Chinos

• Coat: Le Mont St Michel – French Moleskin Work Jacket
• Shirt: Proper Cloth – Indigo Utility Shirt
• Pants: Merz b. Schwanen – Chino01

For some more overlooked pieces in this workwear-that-isn’t-really-wokwear category I pulled two extra European pieces I’ve got.

Up top is a moleskin chore coat, which is to France what the denim jacket is to America: the classic, over-a-century-old workwear garment with roomy pockets and a boxy fit that’s been traditionally used for all manner of outdoor wear in France. I did a whole video (and article) on styling chore jackets, because I think it’s a versatile piece that can dress up and down more easily than other workwear.

For the shirt, we’ve got another unusually versatile kind of workwear called chambray. It’s basically the canvas version of denim: blue and white yarns, but woven in a plain weave like canvas, so it has more of a cross-hatched look to it. Like the chore coat, chambray is deceptively versatile and can dress up and down pretty well.

For pants, this is a wild card: these are chinos from Germant’s Merz b. Schwanen, a brand best known for Carmy’s loopwheel t-shirt on The Bear. Chinos are maybe the best example of workwear that can dress up; their origins are in military workwear, but today they’re very common in business casual settings.

Still, Merz gave their famous chinos a very modern, very roomy high-rise cut that’s pretty dramatic. Nick was so hellbent on not wearing skinny pants that he went with these, but the average guy will prefer the less cartoonishly roomy J Crew’s Classic Chinos, which are also a lot cheaper!

I like how this outfit is workwear inspired, but everything’s just a little off-center in a good way.

4. With a Leather Jacket

• Jacket: Schott NYC – Cafe Racer
• Shirt: Benzak Denim Developers – BWS-01 Work Shirt
• Pants: Buck Mason – Paperback Twill Full Saddle Chino

Just to take the edge off those German chinos, here we’ve got some more classic chinos from Buck Mason. Their “Full Saddle” cut is high-rise and roomy, too, but in a way that’s more commonplace in the 2020s.

When Nick has chinos, he likes to take the opportunity to wear a denim shirt, and he picked one from Benzak Denim Developers in Amsterdam.

Lastly, we’ve got a brown leather flight jacket from Schott NYC, our favorite source for leather jackets. As part of his rationale, Nick explains, “Schott’s Cafe Racer is the best leather jacket. Long story short, I think it’s the perfect balance of understated and edgy for a leather jacket.”

5. Summer Style with Fatigues

• Pants: Taylor Stitch – Surplus Pants (discontinued, try Tellason or Orslow)
• T-Shirt: Teddy Stratford – Crewneck Tedra Shirt

Another solid option for pants you might not have thought about is fatigues.

I feel a bit like a pretender in green fatigues (that’s just me personally) but I’m a huge fan of tan fatigues and brown boots, especially because this style of pant in this kind of fabric — cotton sateen — was designed for warmer climates. So when it’s summer and you still want to wear boots, you can wear fatigues! Because, foreshadowing to our styling mistakes, you really don’t want to wear these boots with shorts.

Nothing beats a t-shirt on top of fatigues, and I just wore one from Teddy Stratford, a small brand in New York that specializes in athletic fits. Where’s the jacket? No jacket, this is your summer outfit!

After a lot of experimentation, I think the extra breezy cotton sateen fatigue pant is the best way to wear boots in summer but you can also look for jeans made of denim that’s 10 ounces per square yard or less; Naked and Famous usually have some that light. But in my opinion, it’s not ideal to wear synthetics or canvas in summer because they don’t breathe as well as sateen or twill.

6: Brown Boots With Black Jeans

• Pants: Iron Heart – 21oz 888 SBG
• Jacket: Heat Straps – Woolen Lumber Jacket
• Shirt: Wonder Looper – Double Heavyweight Long Sleeve
• Hat: Oak Street Bootmakers – 1975 Watch Cap

You know what, this is such a good crowd I’ll send you home with a sixth option: a black jeans fit. I know it’s controversial to wear brown boots with black jeans, but these are expensive boots — most guys won’t want to pay for more than one pair so they have perfect black boots for black jeans!

I wore a neutral shirt, a heavyweight cotton shirt from Wonder Loope, and over the top I threw this really cool wool work jacket I got from Heat Straps, who make them nearby in New Jersey. Filson also sells wool jackets with a similar pattern.

Green is another color that’s usually in the realm of earth tones but can work with cooler black and grey ones, so I feel adding the acid green jacket helps to bring together the mixture of earthy and cool palettes.

How You Shouldn’t Wear Iron Rangers

Mistake #1: Avoid Skinny Jeans

You should not wear skinny jeans with Iron Rangers. These are chunky, meaty boots and if your jeans hug your ankles they will look even more like clown shoes than they already do. (Sorry, Iron Ranger fans. We love them, but our YouTube commenters are constantly calling them clown shoes.)

Mistake #2: Do Not Dress These Boots Up

Do not dress these boots up, not even in business casual attire.

A lot of the time, an Iron Ranger is a guy’s first expensive footwear, and when you’re new to that space, it’s easy to figure out if something’s expensive, then it’s nice, and if it’s nice, then it’s refined.

But Red Wing boots don’t work with suits, especially not the Iron Ranger. Maybe the Beckman boot can go business casual, but let’s save that discussion for another day.

Mistake #3: Avoid Linen

When temperatures start to rise, menswear fans like to bring out their linen and it’s often the only trousers you feel you can wear when it’s hot out. That doesn’t mean you can put work boots underneath them. I know that when it’s summer you miss wearing boots but the airy, floaty fabric and the thick, stompy boots are just a mismatch.

Mistake #4: Don’t Wear Shorts

Perhaps most crucially of all, don’t wear these boots with shorts. We know, we know, just don’t!

Mistake #5: Maybe Avoid Hoodies

Another thing some people might consider a mistake with the Iron Rangers: if you Google Image search outfits with these boots you won’t see anyone wearing them with a hoodie.

Now, this is not that serious. No one will say you’re a failure if you do wear this combo, and I’m not on the team of ‘men over 30 shouldn’t wear hoodies’ either.

But while I think Red Wing’s Moc Toes are sufficiently modern and youthful and streetwear-friendly to go with a hoodie, I think the Iron Ranger is just casual in a different way. Tank tops are casual, sweatpants are casual, that doesn’t mean they vibe with a heritage work boot, you know?

But that’s just my opinion, man.

Wrapping Up: How To Style Iron Rangers

So, you’ve got your Iron Rangers and this handy guide, you now have no excuse to mess things up! Whether you want to go all-American workwear or bring in some military-inspired attire, there are options galore for getting these boots out on the town. Plus, with our easy list of styling faux-pas, you can get a little creative while knowing where the boundaries lie. 

Remember, it’s all about creating a look that’s both stylish and functional, true to the spirit of these classic boots.