How To Wear Work Boots With Jeans (and more!): 5 Different Outfits

by   |  in Style Tips

Unsure how to wear work boots with jeans, or what to wear with them in general? Or maybe you’re still looking for the perfect pair of work boots? In this article, we’ll show you five different outfit ideas, plus give you a few boot options we love.

There are obviously many different types of boots. For an effortless gent with a smart, sharp, casual wardrobe, a solid, durable, brown leather work boot is what I’d suggest.

We envision the ideal pair of brown leather work boots as being a casual yet sleek lace-up style with a plain round toe (cap toe optional) and rubber sole.

We’re not talking heavy-duty, snow-resistant winter boots, or true steel-toe work boots you’d wear on a job site. We’re suggesting a boot with the same rugged aesthetic as a work boot, but with a bit more style and refinement.

This work boot can easily be worn most seasons, and makes sense with both casual and smart casual outfits.

Want our exact recommendations? We love the Medina boots from Beckett Simonon. We’ll be using them in our outfit examples below.

We’re also including several alternatives we wholeheartedly recommend:

Beckett Simonon Medina Boots
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Chippewa Service Boot in Cordovan
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In this, our latest article in the Five Ways to Wear One series, we’re showing you exactly how to wear these brown work boots with jeans, with chinos, with… just about anything.

Wearing brown boots is easier than you might think, and like I mentioned, you can dress it up or down with relative ease (provided you find the right supporting style picks, that is).

The best outfits with brown boots run the gamut, from more rugged to more classic, with plenty of leeway in between.


Brown Boots for Men: Common Questions

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Before we get into the outfits. Let’s discuss the type of brown boots we’re suggesting. There’s a good chance you may have asked some of these questions:

What makes work boots different from combat boots?

The closest cousin to the work boot may be the standard combat boot. Work boots aren’t quite the same as combat boots, although the two do share similarities. 

Combat boots are generally more casual than work boots, with a bulkier silhouette, chunky rubber lug sole, and sturdy construction. Think of a classic pair of Doc Martens, for instance — those are combat boots to a T.

Because of this, combat boots are harder to dress up than work boots

You may also be wondering: Do jeans go inside or outside boots?

While tucking your denim into your boots was quite the rage back in the early 2010s, we’re of the opinion that your jeans should be worn over / outside your boots. It’s a cleaner look, it’s less severe, and it works with all your pants.

When it comes to denim, if you find the right pair (slim or tapered but not skin-tight), they should rest at the top of the shoe at about the ankle (before the work boots curve upward) without bagging or pooling. But first, of course, you’ve got to get the right pair of boots.

Is brown the best color for boots?

If you want a leather color that truly goes with everything — yes indeed, anything you can dream up — a medium to dark brown leather boot is definitely the best color to go for.

Black can be a bit too formal or stark, and tan can be a bit too eye-catching, while at the same time, not pairing up as easily with other colors in your wardrobe. Other colorways, like burgundy or navy, for example, are similarly limiting.

So if you don’t have any work boots for your fall and winter wardrobe, or you want one pair to rule them all, go with a medium to dark brown leather work boot.

Beckett Simonon Medina Boots
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Chippewa Service Boot in Cordovan
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What can I wear with brown work boots besides jeans? 

We’ll get into that more below. We put together five different outfits for you to try, with styles that toe the line between casual and formal… a smart, sharp, casual look, as we like to call it.

For bottoms, think jeans or chinos… and for shirts, think of classic, casual pieces, a la the chambray shirt, a denim jacket, a white Oxford shirt … you get it.

The Best Outfits to Wear with Brown Leather Work Boots 

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Start your engines, or at least kick up that drumroll, because here are our five solid outfit suggestions. You’ll never wonder what to wear with brown boots again 😉

The Classic, Everyday Uniform

This first outfit is a classic. You can wear this just about anywhere, and you won’t ever look too dressed up or dressed down. It checks all the right boxes for a return to the office, some outdoor cocktails, or a small holiday gathering.

And the boots? They add a ruggedness to the overall refined look. The classic brown leather work boots are the anchor of this outfit, and a classic navy blazer is a fun high/low-style pairing that makes sense.

By the way, note the tailored fit and lightweight construction, plus more casual patch pockets. It’s refined, yet casual, which is why the boots work. 

It’s all tied together by a well-fitting pair of faded denim that aren’t overly distressed. The go-to shirt here is a crisp white Oxford shirt, the type that also looks great if you decide to ditch the sportcoat and roll up your sleeves.

In fact, rolling up those sleeves to show off that detailed and refined-yet-wearable watch could just be the way to go.

If the little details make the difference in an ensemble, this outfit is chock full of ‘em. Consider this a daily workhorse.

Laidback & Rugged 

How to make leather work boots suitable for denim? Easy. When you’ve got the right pair, it all starts to fall into place, and that’s what we love about Beckett Simonon’s Medina Boots as shown in these ensembles.

With a design that can be dressed up or down, plus crisp captoe detailing, they’re a near-instant winner if you want a daily pair of leather boots to wear with jeans (and chinos… and more!) 

Here, the casual fall style move is a classic one: Pairing up a sporting-inspired henley with a field jacket that’s at once old-school and yet surprisingly wearable these days. 

Stay warm through the fall and winter with a premium watch cap that adds some visual interest to this look note the textured fabric and dial it in even further with slim inky blue dark denim that’ll break in very nicely over time.

If we had to guess, we’d say this could become your go-to casual outfit, especially if you’re a fan of wearing a classic henley (and really, who isn’t these days!?)

The Fashion-Forward Pick

Yes, you can wear boots with jeans in a way that’s more bold and fashion-forward than one might think (if you want to).

While these brown leather work boots are casual and versatile in their own right, this outfit is taken up a notch thanks to natural-colored five-pocket pants. Consider these to be a sort of jeans-chinos hybrid, made cooler and more trendy thanks to the natural “Birch” colorway. 

Courtesy of Todd Snyder, they play pretty nicely off the chunky sweater shown here, and the off-white and tan color palette is also something you should try if you want to go a bit bolder yet elevated with your next look.

Helping to ground this outfit, of course, are accessories like a crisp leather dress watch (the very same watch shown in the first outfit!), plus a classic peacoat that adds some rugged appeal to this fashion-forward look.

A Fall Or Winter Day Trip

In this outfit, we’re going big on denim. This is the perfect outfit for a fall or winter day trip, and yet another example of how to wear denim on denim (on denim) with boots if you’re going for a casual, rugged style.

Going with multiple denim pieces in various shades — in this case, classic light blue chambray shirting, combined with grey selvedge denim, plus a medium blue denim jacket — gives this outfit a subtle depth and makes it easy to mix and match at will.

Feel free to throw on a henley underneath the chambray shirt as well, for a more layered (and warmer) look.

The entire look is grounded by the pleasingly versatile brown leather work boots that rest stylishly and distinctively beneath the cuff of your grey selvedge denim. And for even more warmth and some seriously cool style, you’re topping it all off with that military-inspired grey peacoat for tried-and-true cold weather good looks.

On the accessories front, a tough field watch is the way to go, given the casual nature of this look, while your trusty watch cap (as seen in other looks here) is also a fitting piece of functionality.

This is the kind of ensemble that’ll work quite well for all those casual fall and winter pursuits, be it a winery visit, a trip upstate, a brewery tour… you get the picture.

Classic, Casual & Timeless

For our final outfit pick, let’s turn back the clock to a time when things were more simple, when brands made gear you could really, really count on, and when style icons like Steve McQueen showed us the way.

That’s where this classic and timeless outfit draws its style inspiration from. It starts from the ground up with your new favorite leather work boots, and we include a bevy of classic picks you can mix and match with many other elements from the other outfits in this post.

From your slub T-shirt (a suitable base layer now or ready to be worn in the spring and summer) to everyday five-pocket pants (toeing the line between jeans and chinos), this is a look that’s even better than you might have imagined.

You can rock the crewneck sweatshirt on its own, or layer it up with one of our field jacket or denim jacket picks. Finally, top it all off with a crisp and iconic field watch

As we’ve said before, it’s all grounded by work boots that look great now, and only get better with age. How can you pass up a look like that?

Beckett Simonon Medina Boots
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Chippewa Service Boot in Cordovan
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Wrapping up: Five Great Outfits to Wear With Brown Boots

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While you may have thought figuring out what to wear with your brown work boots was difficult, hopefully this article illustrates how easy it is.

Wearing boots with jeans and other pants is all about how you choose to style ‘em, and throughout these picks, we hope we’ve driven home that they can be every bit as stylish, versatile and durable as you make ‘em.

Beckett Simonon Medina Boots
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The right pair of brown leather boots offer up crisp style, some rugged appeal, a touch of smart, sharp, casual style, and the exact kind of durability you need to wear on day trips, to the office, or to the brewery.

If that sounds like a pair of boots you need in your life, go right ahead and add ‘em to your cart. We’ll be lacing ‘em up ourselves.

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