Blundstone Classic 550 Chelsea Boots
We mentioned earlier that some of the best mens slip-on boots are actually more akin to work boots than dress boots. This is exactly the pair we had in mind.
Blundstone boots are the stuff of legend, playing off the companys Australian heritage and now worn the world over by everyone from stylish city dwellers to indie rockers to explorers.
Its got to be because of the water-resistant leather upper and the shock-absorbing sole, plus the more casual design of the shoes upper .
Wear these with grey work pants or selvedge denim on chilly fall mornings, and just add your favorite henley for essential casual style.
Mens Leather Slip On Ankle Boots
You found the ultimate one-stop shop for stylish mens and womens clothing from top fashion brands around the globe. Whether youre searching for the latest looks in denim, jackets, outerwear, pants, shorts, skirts, dresses, sweats, hoodies, sweaters, swimwear, uniforms, shoes, tops and beyondits all here.
We can help you pull together a stylish mens outfit, and even show you how to rock the latest in trendy womens clothesall while you browse the biggest names in mens and womens fashion, including Ralph Lauren, Dolce & Gabbana, Coach, Michael Kors, Gap, Old Navy, Tommy Hilfiger, Under Armour and many, many more. Whether you want to overhaul your entire wardrobe, or just need something perfect for that important special occasionyoull find the latest styles in an array of prices, sizes, colors and labels.
Want to wait for the best possible deals on designer clothes, shoes and accessories? We make it easy! Shop now, save all your favorites, and we’ll alert you to any sales, price drops and new promotions across hundreds of retailers and brands. Become a ShopStyle member and get exclusive online clothes shopping deals and the highest cash-back savings powered by Rakuten.
A curated style universe that tailors trends to you.
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 .
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 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. Well cover multiple options when it comes to the best Chelsea boots for men today.
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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.
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 youre anything like us, youre probably not heading out into the great wide open any time soon, but its 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. Theyre remarkably well-made and tough as heck: Ive 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, theres a bit of break-in time, but as with any fine pair of slip-on boots, theyve 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.
Oliver Cabell Chelsea Boots
You might know Oliver Cabell for the brands affordable, super sharp leather sneakers or premium leather lace-up boots, but lets talk about the sleek yet comfy Chelsea boots shown here.
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 wont blow your budget like other Italian-made shoes can! And the light beige suede wears well with white or light wash denim or the darker blue colorway come fall.
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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 .
Chinos or five-pocket pants, with their business casual design and versatile look, also work well with Chelsea boots. And of course, if youve found the right pair of Chelsea boots, you can pair them up with a suit. Well cover your options below.
In terms of pants fabric, Chelseas work well with a more substantial cloth that youd typically wear in the fall and winter months, such as heavy twill, denim, or corduroy trousers. Its 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.
Ping It Up With Men’s Chelsea Boots
Headed out for a night on the town, or looking for a boot option to pair with a suit? Men’s Chelsea boots are a great option to give you the style that you want.
When pairing Chelsea boots with an outfit, be sure to stay crisp and cleanyou’ll want eyes on your shoes, without slouchy pants covering up your style.
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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.
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 youre getting plenty of care and attention to detail for what should prove to be a very agreeable price.
New Republic Sonoma Suede Chelsea Boots
Last but certainly not least: Lets talk about some of the most affordable Chelsea boots, shall we?
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.
Editors note: I own a pair of these, and dont 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 youre looking for something more affordable, you can rest assured these are a good budget buy. BC
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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 theyre crafted from hand-dyed leather and made in Italy.
The NYC-based brand specializes in making affordably priced, sturdily built shoes and boots , which is good news for all of us.
The Duke Chelsea Boots check all the right boxes when it comes to versatile style , and theyre 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.
Men Ankle Slip On Boots
You found the ultimate one-stop shop for stylish mens and womens clothing from top fashion brands around the globe. Whether youre searching for the latest looks in denim, jackets, outerwear, pants, shorts, skirts, dresses, sweats, hoodies, sweaters, swimwear, uniforms, shoes, tops and beyondits all here.
We can help you pull together a stylish mens outfit, and even show you how to rock the latest in trendy womens clothesall while you browse the biggest names in mens and womens fashion, including Ralph Lauren, Dolce & Gabbana, Coach, Michael Kors, Gap, Old Navy, Tommy Hilfiger, Under Armour and many, many more. Whether you want to overhaul your entire wardrobe, or just need something perfect for that important special occasionyoull find the latest styles in an array of prices, sizes, colors and labels.
Want to wait for the best possible deals on designer clothes, shoes and accessories? We make it easy! Shop now, save all your favorites, and we’ll alert you to any sales, price drops and new promotions across hundreds of retailers and brands. Become a ShopStyle member and get exclusive online clothes shopping deals and the highest cash-back savings powered by Rakuten.
A curated style universe that tailors trends to you.
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Going Casual With Men’s Lace Up Boots
Casual boots are a fun look for men, and can help you take simple jeans and a t-shirt to the next level of style. When you decide to go casual with your boots, be sure that you’re wearing your pants in a way that flatters your look.
A small cuff at the hem of your pants can let you show off your boots, while still giving you the clean look that you want. Resist the urge to simply let the hem of your pants fall where it may over your boots, as this can result in an unfinished look.
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.
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.
Lets 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.
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Which Chelsea Slip
We know you have plenty of options when it comes to a great pair of Chelsea boots .
Weve seen quite a few pairs over the years, and the picks weve highlighted above are a solid place to start. If youve been on the fence about trying Chelsea boots, go with an option that wont break the bank.
But if youre 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 cant go wrong.
If you have any questions or comments, hit me up . You can also find join other readers on Effortless Gents , or DM me on !
Are Chelsea Slip
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, its easier to wear sleek Chelsea boots with sharply tailored clothing, dark, slim, denim or other casual pants, yet its more difficult to wear more casual Chelsea boots with tailoring and dressier looks.
So if youre unsure how to do that high/low look, if you look at each individual item in your outfit, and theyre all within the same casual/formal style spectrum, youre good.
Of course, weve provided options below that fit both categories. Still with us?
The point is, the best mens Chelseas add a nice element of versatility to your wardrobe, whether youre going for a more rugged style or wearing something nicely tailored.
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What Color Slip
Short answer: a medium- to dark-brown leather is a solid option. But dont limit yourself, especially if you have room in your wardrobe for more than one pair.
Perhaps youve 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 , then black Chelsea boots could be a very fine starting point to add to your rock n roll wardrobe.
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 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, weve got the perfect pair of ankle boots if you ever want some rich tan leather footwear in your life, which well get into below.
Now that weve ushered you into the world of Chelsea boots, lets stay for a bit. Here are our picks. Give these Chelseas a shot and see what works for you.