Add These Unique Boots To Your Wardrobe This Fall / Winter Season

by   |  in Style Tips

If you want to add a pair of the best men’s slip on boots (also known as Chelseas, and sometimes referred to as ankle boots) to your wardrobe this fall / winter season, we’re highlighting a few of our favorites in this article.

Check your calendar, check the date window on your watch… the fall season is here, and with it comes the need to seriously evaluate your footwear rotation.

Your low-profile sneakers and loafers should slowly but surely be stored away in favor of more rugged footwear to take on the elements and to stand up to everything that fall has to offer (both fall weather and fun fall pursuits). 

Whether it’s a day trip, an orchard tour, or a city stroll (wear a mask!), the right footwear makes all the difference.

The footwear in particular we’re discussing today?

The ever-versatile Chelsea slip-on boot, a style that stands out as some of the best boots for men, season after season. Step right this way to learn more…

(Oh, please, after you.)

 

Slip-On Boots: A Few Common Questions

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Before we get into our recommendations for slip-on boots or Chelseas, you may have a few questions. We wanted to address them here: 

“Wait so, what are Chelsea boots, exactly?”

Chelsea boots are slip-on boots that replace your typical lace-up construction with elastic side inserts and pull-up tabs at the back. These features make non-laced boots easier to put on, as well as give them a more streamlined finish and look.

Chelsea boots can be made from materials like leather or suede in a variety of colorways (more on that in a second). 

tan leather slip on boots with dark jeans
The Kirkdale Chelsea from Herring Shoes

There are plenty of Chelsea boot variations. Some feature a leather sole, slimmer silhouette, and more elegant, slightly pointed toe — Chelseas you can wear with a suit. Others have a more rounded toe with a lug sole (like a work boot) or crepe sole (similar to another favorite casual boot, the Clarks chukka.

Some Chelsea boots sit at ankle height, while others are slightly higher on your leg. We’ll cover multiple options when it comes to the best Chelsea boots for men today.

“Are Chelsea slip-on boots formal or casual? Or are they both?”

The easiest answer to this question might be: “Yes.”

The best ankle boots for men can be dressed up or down, although certain silhouettes are easier to dress up than others.

For example, it’s easier to wear sleek Chelsea boots with sharply tailored clothing, dark, slim, denim or other casual pants, yet it’s more difficult to wear more casual Chelsea boots with tailoring and dressier looks.

Rugged casual outfit with Thursday Boots Duke Chelseas

So if you’re unsure how to do that high/low look, if you look at each individual item in your outfit, and they’re all within the same casual/formal style spectrum, you’re good.

Of course, we’ve provided options below that fit both categories. Still with us?

The point is, the best men’s Chelseas (or maybe you call them slip-on boots) add a nice element of versatility to your wardrobe, whether you’re going for a more rugged style or wearing something nicely tailored.

“What pants go well with Chelsea boots?”

Your typical pair of Chelsea boots — not too rugged or casual, not overly dressy — can work with plenty of different types of pants.

The easy win: a pair of slim or straight fit dark blue or black denim. These are a perfect pairing for your everyday Chelsea boots (cuff the jeans slightly to add some visual interest to the look).

Chinos or five-pocket pants, with their “business casual” design and versatile look, also work well with Chelsea boots. And of course, if you’ve found the right pair of Chelsea boots, you can pair them up with a suit. We’ll cover your options below. 

Tan slip-on boots go well with light and dark blue denim

In terms of pants fabric, Chelseas work well with a more substantial cloth that you’d typically wear in the fall and winter months, such as heavy twill, denim, or corduroy trousers. It’s all about pairing up the style of your Chelsea with the formality of your pants, as we mentioned earlier.

Finally, since most fall and winter pant fabrics are of a heavier weight, both leather and suede Chelseas can rise to the occasion handsomely and stylishly.

“What color slip-on boots should I get?”

Short answer: a medium- to dark-brown leather is a solid option. But don’t limit yourself, especially if you have room in your wardrobe for more than one pair.

Perhaps you’ve got plenty of dark blue denim, grey and tan chinos, and olive or navy five-pocket pants in your wardrobe. In this case, either medium brown leather or black slip-on boots are a solid, versatile buy.

If your wardrobe leans more sleek and sharp (think Alex Turner of the Arctic Monkeys), then black Chelsea boots could be a very fine starting point to add to your rock n’ roll wardrobe. 

dark brown chelsea slip on boots
A pair of Barron’s well-loved Thursday Boots Duke Chelseas

If you fall somewhere in the middle and want Chelsea boots you can wear several days a week, tan leather slip-on Chelseas are a reliable pairing. We think that holds true (as far as color goes) with darn near everything in your rotation. 

Yes, tan leather Chelseas work with most pants. That goes for black and grey denim, as well as olive chinos, navy blue selvedge jeans or navy corduroy pants. In fact, we’ve got the perfect pair of ankle boots if you ever want some rich tan leather footwear in your life, which we’ll get into below. 

Now that we’ve ushered you into the world of Chelsea boots, let’s stay for a bit. Here are our picks. Give these Chelseas a shot and see what works for you. 

What Are the Best Slip-On Boots for Men to Buy Now?

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While you have plenty of slip-on boot options depending on the silhouette you’re going for, the color you want, and the price point you’re working with, these are our all-around favorites.

Beckett Simonon Bolton Chelsea Boots

For Chelsea boots that pair up nicely with most everything in your wardrobe, you could do worse than the sharp, crisply designed Beckett Simonon Bolton Chelsea Boots. 

EG's TOP PICK
Beckett Simonon Bolton Chelsea Boots
$229

Elastic side gussets keep your feet in place, and will never deform or lose shape. The slightly elongated shaft and tapered waist fit comfortably under most suit pants and slim fit trousers. Cool curves and an eye-catching profile give the Boltons a distinct quality.

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From the medium brown full-grain oak leather, to the subtly sleek and stylish design, these slip-on boots check all the right boxes. You can wear them easily with slim blue denim or your favorite pair of chinos, no questions asked. 

Better yet, Beckett Simonon handcrafts each pair of footwear to order, so you’re getting plenty of care and attention to detail for what should prove to be a very agreeable price.

M. Gemi Dritto Chelsea Boots

These luxurious M. Gemi Chelsea boots are assuredly some of the best ankle boots for men, especially if you want a pair made in a refined fashion. In the case of the M. Gemi Dritto Chelsea Boots, that means they’re crafted from hand-dyed leather and made in Italy. 

M. Gemi Dritto Chelsea Boots
$298

These classic boots are hand-dyed in leather and feature a hand-washed leather sole. Plus, they are made in Italy.

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Both of those touches make them some of the best Chelsea boots to wear with a tailored suit or with slightly dressier looks (think navy wool trousers, a white Oxford shirt & a grey cardigan). Investing in the best never looked so good.

Thursday Boots Duke Chelsea Boots 

Perhaps you’ve seen the Thursday Boots name over the years, but never taken the plunge.

The NYC-based brand specializes in making affordably priced, sturdily built shoes and boots (of both the lace-up and Chelsea varieties), which is good news for all of us. 

The Duke Chelsea Boots check all the right boxes when it comes to versatile style (note the dressy silhouette), and they’re going to look right at home with either blue denim or tan chinos. Add your favorite white Oxford shirt and a navy cotton blazer, then consider your next business casual look all set. 

Astorflex Bitflex Chelsea Boots

The team at Huckberry got it right when they said Astorflex was one of the best-kept secrets in the footwear world.

Astorflex Bitflex Chelsea Boots
$195

Handmade in Northern Italy by a family that's been making boots for six generations, these slip-on boots are eco-friendly, handsome as hell, and represent the best value on the market.

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Handmade in Northern Italy, Astorflex specializes in making stylish, sustainable Chelsea boots in a more casual, rugged profile than some of the other options on this list. 

The crepe rubber sole and rugged, casual nubuck leather make the Astorflex Bitflex Chelsea Boots some of the best slip-on boots to rock with your favorite denim. 

Let’s go a step further: Slide ‘em on with stretch blue denim for a long trip in the car this fall, preferably teamed up with a merino T-shirt and a green field jacket for versatility in travel style. 

Oliver Cabell Chelsea Boots 

You might know Oliver Cabell for the brand’s affordable, super sharp leather sneakers or premium leather lace-up boots, but let’s talk about the sleek yet comfy Chelsea boots shown here.

Oliver Cabell Chelsea Boots
$248

The handsome suede upper and crepe sole both come from Italy, where many of the finest shoes in the world are made, yet these won’t blow your budget entirely.

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The best slip-on boots for men can be as dressy as you please, especially when they feature a clean design like these.

The handsome suede upper and crepe sole both come from Italy, where many of the finest shoes in the world are made. Yet these won’t blow your budget like other Italian-made shoes can! And the light beige suede wears well with white or light wash denim (in the spring and summer) or the darker blue colorway come fall. 

Blundstone Classic 550 Chelsea Boots

We mentioned earlier that some of the best men’s slip-on boots are actually more akin to work boots than dress boots. This is exactly the pair we had in mind.

Blundstone Classic 550 Chelsea Boots

This beloved Australian brand knows how to make a Chelsea for the modern man. Made with premium water-resistant supple leather upper and leather lining for added comfort, these boots offer the epitome of durability.

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Blundstone boots are the stuff of legend, playing off the company’s Australian heritage and now worn the world over by everyone from stylish city dwellers to indie rockers to explorers. 

It’s got to be because of the water-resistant leather upper and the shock-absorbing sole, plus the more casual design of the shoe’s upper (it’s bulky and durable rather than slimmed down). 

Wear these with grey work pants or selvedge denim on chilly fall mornings, and just add your favorite henley for essential casual style

Taylor Stitch Ranch Boots in Saddle Tan

Think back to the start of this piece, when we talked about the best color of Chelsea boots to buy.

Taylor Stitch Ranch Boots
$278.40

Yes, Taylor Stitch does footwear, and they’ve channeled all of the brand’s rugged, classic DNA into an impressive line of boots. Inspired by Western boots, these mimic the styling potential of Chelsea boots with a build that’s a bit more hard-wearing for the open road. 

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If you mix in black and blue denim, or other colorways like olive and khaki, when it comes to your everyday pants, these handsomely rugged Taylor Stitch Ranch Boots are for you.

The rich Saddle Tan leather pairs nicely with, well, just about anything, and the silhouette is a play off — you guessed it — classic ranch boots worn on the frontier.

If you’re anything like us, you’re probably not heading out into the great wide open any time soon, but it’s still advisable to have these Goodyear welted Chelsea boots on hand for whatever fall throws at you.

This author just so happens to have a pair of the Ranch Boots. They’re remarkably well-made and tough as heck: I’ve worn them to both the office and to a rock concert without missing a beat. Talk about a pair of the most versatile Chelsea boots, eh? 

Because of the sturdy construction, there’s a bit of break-in time, but as with any fine pair of slip-on boots, they’ve molded nicely to my feet through a season of wear.

In short: My recommendation is to go right on ahead and get yourself these finely crafted Chelsea boots from Taylor Stitch.

New Republic Sonoma Suede Chelsea Boots

Last but certainly not least: Let’s talk about some of the most affordable Chelsea boots, shall we?

New Republic Sonoma Suede Chelsea Boots
$128

The Sonoma Suede Chelsea Boots offer that classic Chelsea boot style without the high price tag.

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Finding a pair of Chelsea boots under $150, the kind that still delivers in terms of quality, is a tricky endeavor  — or at least, it was.

The Sonoma Suede Chelsea Boots offer that classic Chelsea boot style without the high price tag. 

Editor’s note: I own a pair of these, and don’t let the relatively affordable price tag fool you. These have broken in nicely and are very comfortable. Are they as nice as some of the more pricey options on this list? No, but if you’re looking for something more affordable, you can rest assured these are a good budget buy. –BC

Which Chelsea slip-on boots are you buying next?

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We know you have plenty of options when it comes to a great pair of Chelsea boots (or slip-on boots, or ankle boots… whatever you want to call them).

We’ve seen quite a few pairs over the years, and the picks we’ve highlighted above are a solid place to start. If you’ve been on the fence about trying Chelsea boots, go with an option that won’t break the bank.

But if you’re ready to go all in with this footwear classic, look for a solid, sturdy pair, preferably made from rich leather and featuring a silhouette you can style with chinos or jeans.

Choose from the handsome pairs we featured above and you can’t go wrong.

If you have any questions or comments, hit me up on Twitter. You can also find join other readers on Effortless Gent’s Facebook page, or DM me on Instagram!