How to wear men’s boots: styles and outfits for 2021

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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 harder and harder by the day, nothing less than a pair of warm boots will be able to keep your toes from freezing from now on. And besides, have you ever walked on a crispy leaf while wearing boots? You can’t beat this feeling. Now your only obstacle is knowing exactly how to wear boots.

Before we can explain how to wear boots, we need to clarify what kind of boots we are talking about. Do we mean Chelsea boots, with their distinctive minimalist leather aesthetic and elastic side panels, or heirloom-style work boots designed to look good as hell while still being able to take a beating? If you are looking for advice on the style of Chelsea boots. we describe how to wear them this season. But are there other fall boots ready to be styled in your wardrobe, such as the casual chukka boots or the leather lace-up shoes designed to be worn with your more formal duds? It could be any of the above. So we’re going to give you some style tips for each of them – that way, whatever pair of boots you choose to wear, you’ll know how to do it in style.

Work boots: how to wear them

In the early ’10s, heirloom leather boots took the menswear world by storm. But as the name suggests, they’ve been around a lot longer than that. And for good reason: this is a timeless style that not only looks rugged and masculine, but will also last you for years to come.

As for their style, you’re going to want to lean into that heirloom workwear vibe. Look for strong, durable fabrics with a certain texture like denim and canvas to wear with your boots. Knits will also work, the warmer the better. Basically, if this looks like something you could wear on a cool fall day, it will probably work with a pair of heirloom style boots.

Here’s a little inspiration:

J.Crew cable-knit cashmere sweater

Blue cashmere sweater on a plain background.

Fall isn’t just the best time to wear work boots, it’s also the time for sweaters. And this J.Crew cable knit option is a solid, affordable choice.

Levi’s 501 Original Fit Jeans

The Levi's 501 Original Fit jeans are paired with a white t-shirt.

The style that started it all, Levi’s 501 jeans are about as old as they get. Wear them with confidence – and any work boot.

Red Wing Heritage 6 “Moc Toe Boot

A pair of Red Wing Heritage 6 boots

Put your best foot forward with the 6 inch moc toe boot from Red Wing – the rubber sole provides all the comfort you need for a day on the feet.

Chelsea boots: how to wear them

Originally designed as a riding boot in the 19th century and then reappeared in the swinging London crowd of the ’60s, the swing Chelsea boots (see what we did there?) Modern in style. The key here is to wear your pair with clean, minimalist styles. Solid colors can be a great choice – whether that means a more monochrome outfit or something more contrasting, it’s entirely up to you.

Here’s a little inspiration:

Buck Mason Vintage Denim One-Pocket Shirt

Buck Mason vintage denim one-pocket shirt on a solid background.

Although it started out as a workwear staple, the denim shirt has recently gained some sort of streetwear appeal, especially in a dark wash like this Buck Mason pick.

Bonobos extra stretch travel jeans

Bonobos Extra Stretch travel jeans are paired with a blue shirt and white sneakers.

Keep things clean under the belt by donning a pair of black or charcoal jeans. Bonobos put a little stretch in theirs for more comfort.

Saint Laurent Wyatt suede Chelsea boots

Saint Laurent Wyatt Suede ankle boot on a plain background.

Contrast all the dark colors at the top by spotting a pair of light beige suede Chelseas below. There is no better pair than the Saint Laurent Wyatt boot.

Chukka boots: how to wear them

There is something about the way desert boots are designed – perhaps the more relaxed, unstructured top or the simple way to lace them up – that makes them one of the more versatile styles. You can keep that laid back attitude by wearing them with equally casual clothes, or you can dress them up by pairing them with more user-friendly clothes. Or you can land somewhere in the middle. Your call.

Here’s a little inspiration:

Taylor Stitch Henley Heavy Bag

Brown Taylor Stitch Heavy Bag Henley Shirt on white background.

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

Chino Alex Mill Field

Alex Mill Field Chino on plain background.

A wide leg chinos – like this beautiful pair from Alex Mill – will complement the laid back, laid back vibe of your desert boots and give a trendy look to boot.

Clarks Desert II Chukka Boots

Clarks Desert II Chukka Boot on white background.

Each Clarks Desert boot is crafted from soft suede with a design that’s as relaxed as you will feel when you feel the rubber sole underfoot.

Lace-up boots: how to wear them

Think of leather laces as the dress shoes of the boot world. Would you wear a pair of waxed brogues with worn jeans? Probably not. The same applies to a nice pair of lace-up leather boots. Reserve them for dress pants or chinos, preferably with a pretty button placket, a blazer or an overcoat to complete the look.

Here’s a little inspiration:

Non-iron supima cotton dress shirt

Non-ironing Supima cotton dress shirt in suitable fabric, carefully folded on a white background.

One thing you need to know when it comes to plaid: the smaller the tile, the easier it is to style. That’s why we love this Proper Cloth shirt – the pattern is colorful, but not too painful to match with a tie.

Banana Republic Italian Slim Sharkskin Suit Trousers

Banana Republic Italian sharkskin suit trousers on a white background.

Banana Republic has been making office wear for the modern man for years, so we trust them to make a sturdy pair of dress pants like this one.

Beckett Simonon Lorenzo Boots

Beckett Simonon Lorenzo Boots on a plain background.

Beautiful waxed leather? To verify. Subtle cap-toe style? To verify. Cowhide leather lining? Also check. Beckett Simonon nailed these next level lace-up boots.

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