Best Men’s Dress Boots

Men’s dress boots are seriously in fashion right now, and there’s never been as much choice available, no matter how much you’re looking to spend. A bespoke pair of hand-stitched and finished-leather brogues can seem pricier but are well worth the investment if a fashionable change in your footwear is what you’re looking for.  Perhaps you feel like updating your style a bit and interchanging your regular dress shoes with a more comfortable pair of boots instead?

There are all kinds of styles you can go for that look perfectly presentable and indeed effortlessly stylish worn with either your business attire or for a more casual look teamed with jeans and a white shirt. Boots aren’t just for the winter months either. Yes, they’re the perfect footwear for when it’s cold and damp, particularly if you’ve opted for a durable waterproof leather pair, but you can also get fantastic Chukka-style desert boots in light-weight canvas options for the summer months too, which you can wear with or without socks.

The dress boot is an impressive and supremely versatile piece of men’s footwear, and we’re going to be reviewing five of our top recommendations across the various categories today from Chelsea to Oxford to Chukka’s, round toed, pointy-toed, slip-on and lace-up. We’ve selected a range that should appeal to most tastes and budgets and are just perfect for the modern and dapper gent who always likes to look sartorially elegant and debonair. If that sounds like you, then stick around as we review the best men’s dress boots currently available.

Comparison Chart

Giorgio Brutini Men's 660591 Boot,Black,8.5 D US
Rockport Men's Essential Details Waterproof Dress Chukka Boot,Black,7 W US
Bruno Marc Men's Bergen-02 Brown Leather Lined Oxfords Dress Ankle Boots - 9.5 M US
Giorgio Brutini Men's 80575 Dress Boot,Black,8.5 W US
Mens Dress Boots Oxford Lace-up (8.5 M US, Tan-6)
Giorgio Brutini Men's 660591 Boot,Black,8.5 D US
Rockport Men's Essential Details Waterproof Dress Chukka Boot,Black,7 W US
Bruno Marc Men's Bergen-02 Brown Leather Lined Oxfords Dress Ankle Boots - 9.5 M US
Giorgio Brutini Men's 80575 Dress Boot,Black,8.5 W US
Mens Dress Boots Oxford Lace-up (8.5 M US, Tan-6)
Giorgio Brutini Men's 660591 Boot,Black,8.5 D US
Giorgio Brutini Men's 660591 Boot,Black,8.5 D US
Rockport Men's Essential Details Waterproof Dress Chukka Boot,Black,7 W US
Rockport Men's Essential Details Waterproof Dress Chukka Boot,Black,7 W US
Bruno Marc Men's Bergen-02 Brown Leather Lined Oxfords Dress Ankle Boots - 9.5 M US
Bruno Marc Men's Bergen-02 Brown Leather Lined Oxfords Dress Ankle Boots - 9.5 M US
Giorgio Brutini Men's 80575 Dress Boot,Black,8.5 W US
Giorgio Brutini Men's 80575 Dress Boot,Black,8.5 W US
Mens Dress Boots Oxford Lace-up (8.5 M US, Tan-6)
Mens Dress Boots Oxford Lace-up (8.5 M US, Tan-6)

Giorgio Brutini Men’s Chelsea Dress Boot

Giorgio Brutini Men's 660591 Boot,Black,8.5 D US

First up we’re reviewing a Chelsea boot from the Giorgio Brutini collection. The Chelsea boot began life in England in the mid-19th century and wasn’t popularized globally until relatively recently. It’s now a huge favorite on stylish feet around the world and is characterized by its pull-on design with its elasticated sides. It was a boot that adorned the feet of many mods throughout 1960’s Britain and was loved by fans of the rock and pop world.

More recently, with a move towards formal menswear and sharp dressing being favored by many men for both their business and casual looks, the Chelsea boot has enjoyed a revival, thanks to that slim-line and attractive silhouette, the side panels and heel pull-tabs.

From Giorgio Brutini, our first boot is all about modern comfort and contemporary style, as typified by this label. They manufacture shoes for the modern man with a touch of irreverence, confidence, and who certainly knows and owns his style. It’s such an easy to wear design and style which can just be pulled on and off thanks to that heel tab.

Always a winning choice, these Chelsea style boots can be dressed both up to look just as elegant worn with a business suit as it does with jeans for a casual leisure look. Giorgio Brutini has opted for a leather construction which adds to the refinement of this dress boot which comes in a wide selection of sizes. This particular boot is in black only but is still a versatile and wearable choice. With the cushioned insole padding it’s also an exceptionally comfortable boot to wear and won’t require any extended periods of breaking in. Always a winning choice, these leather Chelsea boots offer an upscale alternative to your regular shoes and are sure to grab attention for all the right reasons.

Review of Key Features

Twin Gore Style

These stylish black leather imported Chelsea boots are what is known as twin gore boots, with two comfortable elasticated sides.

Pull-on Loop

They feature a pull-on loop at the back so are easy to slip on and off.

Ankle Height

They feature an elegant design aesthetic and are ankle height. The boot opening measures approximately 12.5” around, so they are streamlined yet comfortable.

Padded Insoles

They have comfortably padded insoles which provide an easy fit choice.

Stylish and Versatile Appeal

In waxed black leather, they are an ultimately wearable, versatile and stylish modern boot that will go with a wide range of outfit choices for a brilliant yet casual dress look.


  • 100% black waxed leather
  • Synthetic sole
  • Elasticated gores
  • Padded comfort insole
  • Stylish and versatile
  • Durable and hard wearing
  • Great value for money


  • Run a little small in size


Rockport Men’s Chukka Dress Boot

Rockport Men's Essential Details Waterproof Dress Chukka Boot,Black,7 W US

Next up in our best men’s dress boots review, we have something from popular brand Rockport which is in the more casual Chukka boots style. Chukka derives its name from the sport of Polo and these boots are also sometimes referred to as desert boots. A Chukka boot will mainly be typified by having certain key features although different brands, of course, embellish and adapt their boots.

As a general rule, though, a Chukka is a lace-up ankle boot that should only reach ankle height and no higher. It will have two or three lacing eyelets only and a rounded-toe design. They generally have thinner style soles and historically were unlined. Popularly manufactured in suede or leather, they are often preferred as a lightweight summer alternative to a shoe, especially if they are in soft pale calfskin suede.

This offering from Rockport is part of their popular, mid-priced range and is 100% full-grain leather with a rubber sole and lightweight, shock absorbing heel cushioning. This makes these a supremely comfortable and easy-to-wear dress shoe that looks as good as it feels to wear. They also feature moisture-wicking technology as well as a DEWIX anti-microbial lining.

Fully waterproof, they’re the perfect Chukka boot for all kinds of weather conditions and occasions and look equally as good with a suit as they do a pair of denim jeans.

Review of Key Features

Featherweight Design

Light yet durable, each element of this Rockport dress boot has been hand selected to be feather-light, functional and extremely durable

Slip Resistant Soles

These classic Rockport Chukka style boots deliver a stable and dependable experience every step of the way no matter what the external weather conditions or surface you’re traversing. Featuring slip resistant soles as well as shock absorbing heel cushioning they’re a supremely comfortable and dependable shoe.

Hydro-Shield Waterproof Protection

Wear these boots whatever the weather thanks to their Hydro-Shield Waterproof construction which actively repels water thanks to Rockport’s exclusive use of the material and a process of seam sealing. They feature a specially formulated waterproofed insole and ensure maximum comfort and dryness protection.

Extended Size and Widths Available

Rockport appreciates that our feet come in different shapes and sizes, so their range of dress boots are available in both narrow and wide shoe sizes ensuring you always have the option to select the most comfortable fitting for you.


  • 100% full-grain leather construction
  • Slip-resistant
  • Hydro-shield waterproof design
  • Narrow and wide widths
  • Extended size options
  • All-weather chukka style ankle boot
  • DEWIX anti-microbial lining


  • Slightly uncomfortable foot soles


Bruno Marc Men’s Oxford Dress Boot

Bruno Marc Men's Bergen-02 Brown Leather Lined Oxfords Dress Ankle Boots - 9.5 M US

We’ve chosen another classic men’s dress boot to review next in our Best Men’s Dress Boots review. This time we’re going to the brand Bruno Marc and looking at his take on their Oxford boots which can also come as a more traditional and very popular shoe as well. The Oxford most certainly got its name from the British University city and was a firm favorite of its students back in the 1800’s so it’s a shoe steeped in history. Since then it’s become synonymous the world over with business and every attire and is the perfect boot to pull off with a suit.

Regarding key characteristics, an Oxford, like this Bruno Marc example, features a closed-lacing system and an elongated toe that may come with or without a cap toe. Typically they’ll be three-part construction, all leather with a distinctive stitched sole. While it’s a very traditional and stable looking shoe, it’s also very stylish and sophisticated, making this style popular the world over. They can also sometimes come with a pretty hefty price tag.

Not so though with this fine boot from Bruno Marc which is budget-friendly. OK, so the compromise is that you aren’t getting a leather boot, this is, but it still manages to look elegant and refined and has a durable sole with classic stitching and a wooden heel height measuring approximately 1”.

Available in a wide range of classic brown and black colors, at these prices, we’d recommend you stocked up. To our mind, while it’s marketed as an Oxford, this is, in fact, more like a Chukka boot with the low ankle height and that three eyelets lace-up design. There’s also a slight platform at 0.5” which gives that extra bit of height and confidence. All around this is one stylish and affordable boot with a classic toe design as well as a non-skid outsole, and latex cushioned footbed for your added comfort.

Review of Key Features

Everyday Comfort and Style

The key characteristic of this boot is its comfort level. It’s fully lined and features a comfortable latex-cushioned footbed to support your foot all day long fully and to allow it to breathe.

Secure and Durable Construction

With a non-skid outsole, you can confidently strive forward in this Bruno Marc boot no matter what the surface. You will have a good grip and firm footing.

Classic Lace-up Design

The secure hold lace-up design not only adds to the design appeal of these boots but also ensures a comfortable and secure day long fit. Coupled with the classic toe, this adds a touch of stylish sophistication as well as practical and wearable elegance to this ankle boot.

Extensive Color Options and Sizing Available

The boot comes in a range of classic and contemporary faux leather upper finishes including brown, dark brown, tan and black so there is an option and a size to suit all styles and personal tastes.


  • Durable human-made construction
  • Sturdy non-skid rubber sole
  • Elegant stitching
  • Wide choice of colors and styles
  • Budget friendly pricing
  • Secure lace-up closure
  • Comfortable cushioned footbed


The material of the boots smells a bit at first


Giorgio Brutini Men’s Pointed Toe Dress Boot

Giorgio Brutini Men's 80575 Dress Boot,Black,8.5 W US

We’re back with Giorgio Brutini now for our next dress boot which is something very different in style and design aesthetics than the other boots we’ve so far reviewed today and is certainly intended for the more sartorially elegant among you who have a distinctive and unique personal style. We say that because this boot is in what we’d describe as a Cuban heel style and may not be to everyone’s taste.

As you would expect, what it does deliver is that little bit of extra height which some guys might appreciate. It’s a very stylish-looking ankle boot that has a full inside zipper closure. The other boots we’ve looked at so far have either been typified by that Chelsea-style pull-on design or the Oxford full-lace closure, so a zippered dress boot is something a little bit different and is certainly easy to take on and off.

The boot itself is constructed from a shiny, polished leather upper which gives it that sophisticated dress boot finish and is combined with a soft leather lining as well as a genuine leather outsole. This is one boot for when you want to dress to impress thoroughly. There’s an extensive choice of colors and sizes from a classic black to a very contemporary and striking cream.

We’d say that this has a much more retro rather than classic look, especially with that pointed toe, tonal stitching, and overlays. It’s not a boot that everyone can pull off, and it certainly lends itself to a particular style. The heel height is 2 inches so will give a nice bit of additional height to the wearer and the boot opening measures approximately 11 inches around, so it’s a slim and elegant silhouette around the ankle. It’s certainly a stylish and well-constructed men’s dress boot and perfect if you like to stand out from the crowd and stamp your personality on your outfits.

Review of Key Features

Genuine Leather Construction

This dress boot is constructed from pure 100% Cabran kidskin leather including a leather sole and comes in a wide choice of colors and sizes.

Stylish Retro-inspired design

The unique styling of this men’s ankle boot set it apart. With a side zipper closure, a pointed toe and that Cuban heel it’s a very stylish boot for the man who knows his style. With tonal stitching and overlays, it creates a very distinctive silhouette.

Easy to Pull On and Off

Thanks to that instep zipper, these are very easy to wear boots that don’t feature fiddly laces or require any effort from the wearer to pull on.


  • 100% leather Cabran calfskin construction
  • 2-inch Cuban-style heel
  • Retro-inspired design with tonal stitching
  • Pointed toe and ankle height design
  • Instep zipper
  • Good range of contemporary color choices
  • Versatile and easy to wear


  • Thinly designed leather soles


Zriang Men’s Leather Lined Oxford Derby Dress Boot

Mens Dress Boots Oxford Lace-up (8.5 M US, Tan-6)

For our final recommendation today in the category of best men’s dress boots, we’re looking at what the brand Zriang has to offer in the form of their classically styled and elegant lace-up boot. So far we’ve looked at examples of the Chukka, the Chelsea and also the Oxford but what about the Derby, another popular choice, similar in looks to the Oxford but slightly more versatile in that it can easily be worn with smart or casual attire and is popularly available in both suede and leather. As opposed to the closed lace-up design of the Oxford, a Derby features open lacing which means that the quarters are stitched on top of the vamp which allows for more of a sense of freedom and a looser fit. They will typically feature an elongated or round tow with a stitched leather sole.

This boot from Zriang is a bit of a mash of a few of the most popular men’s dress boot styles and is indeed very elegant, featuring a smooth leather lining that provides plenty of foot ventilation. In a wide range of the most popular colors, it’s undoubtedly a very attractive looking, comfortable to wear as well as a cost-effective option. With a latex cushioned footbed for enhanced shock absorption, you could comfortably wear this boot all day long.

It’s characterized style-wise by that typical lace-up construction that delivers at once both a secure but flexible and adjustable fit. Zriang is all about making shoes and boots which embody the qualities of a gentleman, which is where the name is derived from. It represents Z – zealous, R- romantic, A – ambitious, N – noble, and G – generous. If that sounds just like you, then these are the dress boots you need to be wearing on your feet.

High-quality construction, with stylish, elegant design features and performance factors that meet the modern demanding lifestyle. These boots are versatile and will work just as well with your casual leisure outfits as they will your business attire. An excellent match for a whole host of occasions and outfits.

Review of Key Features

Premium PU Leather Construction

Fully premium PU leather upper and breathable lining adds a touch of elegance with a gloss finish which is also delicate to the touch.

Fully Breathable and Comfortable Insole

Designed with a soft, moisture-wicking absorbent foam insole for all-day comfort and support. Proven to control and manage both bacteria and unwanted odors effectively.

Sophisticated and Stylish Detailing

Exceptional attention to detailing completes these beautiful boots with their delicate stitching and waxed shoelaces, blind eyelets and that lace-up secure closure.

Comfortable and Durable System

The synthetic sole provides plenty of traction and durability as well as delivering long-wearing comfort as well as support.


  • Breathable insole
  • Moisture wicking
  • Elaborate and stylish design aesthetics
  • Quality, durable construction
  • Premium PU leather upper and liner
  • Fully breathable
  • Easy maintenance and long wearing


  • Not real leather


Final Recommendation

Whether you prefer the closed lace look of a classic Oxford or Derby boot or are a fan of the more flexible Chelsea boot, there will be something on this best men’s dress boot review today that will appeal to your own unique style and taste. When looking for the best dress boots, it’s essential that you purchase a pair that are not only stylish and that you will be able to wear with a range of your business and casual outfits, but which are also comfortable too.

You will likely be wearing your boots for an extended period so look out for features like cushioned insoles that will deliver a more flexible and supportive fit. Also, pay attention to the soles. An all-leather construction is excellent and a very sophisticated look but if you do intend wearing in all kinds of weather conditions, you need to go for something that provides more traction and better grip and support across a variety of surfaces.

Whether you prefer a highly polished and retro-inspired look, something that is more relaxed and casual or a boot that is solidly classic and traditional in both its design and manufacturing, our cross-section of the best men’s boots we’ve currently located to purchase today should check all the various boxes, with something for everyone included.

All you need to decide is whether you fancy a pair that are Oxford, Derby, Chukka, Chelsea, or even Cuban inspired!


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