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

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. Have you ever stepped on a crunchy leaf while wearing boots. You can’t beat that feeling. The only thing that is left now is how to properly 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. Are we referring to Chelsea boots with their minimalist leather look and elastic side panels? Or heritage-style work boots that can take a beating while still looking great? If you’re looking for tips on styling Chelsea boots. We give you our tips on how to wear them this fall. There are many other fall boots that you can style, such as the laid-back Chukka boots and the leather lace ups. These boots can be worn with more formal outfits. 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’We’ll show you how to do it well.

Work Boots: How to Wear Them

In the early days ‘10s, heritage leather boots took the men’They are taking the fashion 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.

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As for styling them, you’re going to want to lean into that heritage workwear vibe. Wear your boots with tough, durable fabrics that have texture such as denim or canvas. Knitwear is also possible, but 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. This J.Crew cable knit option is a solid and 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 styling. It is important to wear your pair with simple, minimalist styles. Solid colors can be a great choice — whether that means a more monochromatic outfitYou can choose to use a higher-contrast color or something else entirely.

Here’s a little inspiration:

Buck Mason Denim Vintage One-Pocket Shirt

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

The denim shirt started out as a workwear staple. However, it has been given streetwear appeal in recent years, especially when it is made in a dark wash, such as this Buck Mason pick.

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Bonobos Extra Stretch Travel Jeans

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

A pair of charcoal or black jeans will keep you clean below your belt. Bonobos added stretch to their jeans for added comfort.

Saint Laurent Wyatt Suede Chelsea Boots

Saint Laurent Wyatt Suede Boot on a plain background.

A pair of light tan suede Chelseas will contrast with all the dark colors. There’s no better pair than the Saint Laurent Wyatt boot.

How to wear Chukka Boots

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 find somewhere in between. It’s your call.

Here’s a little inspiration:

Taylor Stitch Heavy Bag Shenley

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

Henley shirts can be worn immediately as an essential garment. outfitYou will feel more sophisticated and elegant, but still feel like a basic. For example, take a look at this Taylor Stitch option.

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

Leather lace-ups can be described as the dress shoes of boot world. Would you wear a pair polished oxfords paired with a pair of worn-in jeans. It’s unlikely. This is true for a pair of lace-up boots. These can be worn with dress pants or chinos. To finish the look, you can pair them with a nice button-down, jacket, or blazer.

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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.

When it comes to plaid, there is one thing you need to know: The smaller the check the more easy 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.

Beautiful polished leather? Check. Subtle cap-toe styling? Check. Vachetta leather lining Also, take a look at. Beckett Simonon’s nailed these next-level lace-up boots.

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