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How To Wear Men’s Boots: Styles and Outfits for 2021

Man tying his one of his boots.

We’ve said it before and we’ll say it again: there’s no better time than fall to wear a great pair of boots. With the weather getting dicier by the day, anything less than a warm pair of boots won’t be able to keep your toes from freezing from here on out. And besides, ever step on a crunchy leaf while wearing boots? You can’t beat that feeling. Now your only hurdle is knowing exactly how to wear boots.

Before we can go ahead and explain how to wear boots, we need to clarify what kind of boots we’re talking about. Do we mean Chelsea boots, with their distinctive minimalist leather aesthetic and elastic side panels, or heritage-style work boots built to look handsome as hell while still being able to take a beating? If you’re looking for tips on styling Chelsea boots. we break down how to wear them this season. But there are other fall boots ready to be styled in your closet such as the laid-back chukka boots or the leather lace-ups designed for wearing with your more formal duds? Could be any of the above. So we’re going to go ahead and hook you up with some styling tips for each of ‘em — that way, no matter what pair of boots you choose to wear, you’ll know how to do it in style.

Work Boots: How To Wear Them

Back in the early ‘10s, heritage leather boots took the men’s style world by storm. But as their name implies, they’ve been around for way longer than that. And for good reason: They’re a timeless style that not only looks rugged and masculine but also will last you for years to come.

As for styling them, you’re going to want to lean into that heritage workwear vibe. Look for tough, durable fabrics with some texture like denim and canvas to wear with your boots. Knitwear will also work, the warmer the better. Basically, if it feels like something you might wear on a crisp fall day, it’ll probably work with a pair of heritage-style boots.

Here’s a little inspiration:

J.Crew Cashmere Cable-Knit Sweater

Blue Cashmere sweater on a plain background.

Fall’s not only the best time to wear work boots, it’s also sweater weather. And this J.Crew cable-knit option is a solid, affordable choice.

Levi’s 501 Original Fit Jeans

Levi’s 501 Original Fit Jeans partnered with a white tee.

The style that started it all, Levi’s 501 jeans is about as heritage as it gets. Wear ‘em with confidence — and any work boot.

Red Wing Heritage 6” Moc Toe Boot

A pair of Red Wing Heritage 6” Moc Toe Boots.

Put your best foot forward with Red Wing’s 6-inch moc toe boot — the rubber sole offers all the comfort you need for a day on your feet.

Chelsea Boots: How to Wear Them

Originally designed as a riding boot in the nineteenth century, then popping up again in the ‘60s Swinging London crowd, Chelsea boots swing (see what we did there?) modern in terms of styling. The key here is to sport your pair with clean, minimalist styles. Solid colors can be a great choice — whether that means a more monochromatic outfit or something more high-contrast is entirely up to you.

Here’s a little inspiration:

Buck Mason Denim Vintage One-Pocket Shirt

Buck Mason Denim Vintage One-Pocket Shirt on a plain background.

Despite starting as a workwear staple, the denim shirt has gotten a kind of streetwear appeal of late, especially in a dark wash like this Buck Mason pick.

Bonobos Extra Stretch Travel Jeans

Bonobos Extra Stretch Travel Jeans partnered with blue shirt and white sneakers.

Keep things clean below the belt by throwing on a pair of black or charcoal jeans. Bonobos put some stretch in theirs for extra comfort.

Saint Laurent Wyatt Suede Chelsea Boots

Saint Laurent Wyatt Suede Boot on a plain background.

Contrast all the dark colors up top by spotting a pair of light tan suede Chelseas below. There’s no better pair than the Saint Laurent Wyatt boot.

Chukka Boots: How to Wear Them

There’s something about the way that chukka boots are designed — maybe the more relaxed, unstructured top or the simple way you lace ‘em up — that makes them one of the more versatile styles out there. You can keep that laid-back attitude going by wearing them with clothes that are equally relaxed, or you can dress them up by pairing ‘em with more business-friendly attire. Or you can land somewhere in the middle. Your call.

Here’s a little inspiration:

Taylor Stitch Heavy Bag Henley

Brown Taylor Stitch Heavy Bag Henley Shirt on a white background.

Henley shirts are one of those essential garments that immediately make an outfit feel that much more stylish and intentional, while still feeling like a basic. Just look at this Taylor Stitch option for example.

Alex Mill Field Chino

Alex Mill Field Chino on a plain background.

A wide leg chino — like this handsome Alex Mill pair — will complement the relaxed, casual vibes of your chukka boots, and look on-trend to boot.

Clarks Desert II Chukka Boot

Clarks Desert II Chukka Boot on a white background.

Each Clarks Desert Boot is made from soft suede with a design that’s just as relaxed as you’ll feel when you experience the rubber sole underfoot.

Lace-Up Boots: How to Wear ‘Em

Think of leather lace-ups as the dress shoes of the boot world. Would you wear a pair of polished oxfords with a worn-in pair of jeans? Probably not. The same applies to a nice pair of lace-up leather boots. Reserve these for dress pants or chinos, preferably with a nice button-down, blazer, or topcoat to finish off the look.

Here’s a little inspiration:

Proper Cloth Non-Iron Supima Cotton Dress Shirt

Proper Cloth Non-Iron Supima Cotton Dress Shirt folded neatly on a white background.

One thing you should know when it comes to plaid: The smaller the check, the easier it is to style. That’s why we love this Proper Cloth shirt — the pattern is colorful, but not too much of a pain to match a tie with.

Banana Republic Slim Italian Sharkskin Suit Pant

Banana Republic Slim Italian Sharkskin Suit Pants on a white background.

Banana Republic’s been making office-ready apparel for the modern man for years, so we trust them to make a solid pair of dress pants like these.

Beckett Simonon Lorenzo Boots

Beckett Simonon Lorenzo Boots on a plain background.

Handsome polished leather? Check. Subtle cap-toe styling? Check. Vachetta leather lining? Also check. Beckett Simonon’s nailed these next-level lace-up boots.

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