We don’t always have a big budget available in order to enjoy the highest quality boots. Furthermore, there’s a lot of cheap footwear out there at attractive prices that often feels too good to be true. Unfortunately, in most cases, they are too good to true…
Having tried numerous pairs of inexpensive bots, we’ve assembled this list of the Best Dress Boots Under $100:
- Cuban Heel: Giorgio Brutini Calloway
- Chukka Boot: Timberland Earthkeepers Brook Park
- Chukka Boot: Nunn Bush Savage Plain Toe
- Chelsea Boot: Giorgio Brutini Aaron
- Monkstrap Boot: Stacy Adams Kason
- Cuban Heel: Giorgio Brutini Blackjack
If a particular pair has caught your eye, you can use the links above to jump ahead. Afterwards, we’ll talk a bit about the price point and what you can expect for your money.
Quick Buyer’s Guide
In a hurry and don’t have time to read our detailed breakdown? Use the Quick Buy Guide to be taken straight to the retailers. However, if time is on your side, we recommend that you learn more about each shoe first.
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Cuban heel boots are stylish and a daring addition to your wardrobe. If you want to channel your inner Latin spirit, these are stunning boots with a full inside zip closure. The uppers are also Cabra kidskin, which provides a supple and flashy appearance.
How To Wear
An elegant choice when wearing business casual or even with a business professional suit, these boots have a particular aesthetic that isn’t for everyone. Nevertheless, they’re particularly stylish and blend seamlessly into they right wardrobe.
Although they’re also available in brown, we have a preference for the black leather. Given their streamlined design, they’re much better as dressier formal boots.
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We’re very fond of these affordable chukka boots from Timberland. Featuring a full-grain leather upper, they’re also designed with the brand’s anti-fatigue comfort technology as well as their ecological Green Rubber outsole.
How To Wear
As chukkas go, these are actually quite dressy. They’ll look great as business casual boots but you could always pair them with a relatively dressed-down suit for a unique and relaxed look.
Only available in black, we think that this is the best possible colour for these boots anyway. This renders them quite dressy especially when taking the budget into account.
This alternative chukka boot style from Nunn Bush offers an elegant touch of brogueing perforations as well as a burnished leather appearance. Using premium leather as well as stylish contrast from the sole stitching, they’re particularly impressive for the price point.
How To Wear
Again, these are boots that can be worn for both business casual and professional wear. We actually find them to be dressier than Timberlands above and would certainly recommend them more for suit wear.
Three colour options are available including black and tan. However, we prefer the brown as they’ll be more versatile across several dress codes. Nevertheless, the black boots offer an extra level of formality, which may be handy if worn professionally.
An alternative yet common boot style is the Chelsea, which we’d certainly recommend for more formal occasions over the chukka. Giorgio Brutini offer these wonderfully affordable Chelsea boots that are both stylish and comfortable to wear.
How To Wear
Thanks to the graceful shape of the upper and understated details, these are perfect for business professional wear. However, you can also have them when dressing down as they’ll fit right into business casual styles too.
Despite being only available in black, we feel that this would be the best colour option available anyway. Given that they’re a more formal boot style, this would be the most appropriate colour to choose.
A unique specimen, the Kason by Stacy Adams is a double monkstrap boot with dimensions similar to chukkas. With a balmoral cap toe and brogueing perforations, they’re very interesting with an original style.
How To Wear
Depending on the colour, they’re either great for casual and business casual wear or more formal occasions. Whilst the tan is quite laid-back, the black would be ideal for both business professional and cocktail attire.
Both colours are great but it depends on your needs. If you’re looking for a relatively formal dress boot, opt for the black. Alternatively, the tan boots are ideal for casual occasions when heading out.
Another creation by Giorgio Brutini, these Cuban heel boots are a little more subtle than the ones above. If you’re looking for a more understated design, these are ideal. Furthermore, they borrow from Chelsea boots with a slip-on design.
How To Wear
Dressy enough for business professional wear, they’re also great for more casual use. Whether it’s a day out or at a party, they’re very stylish with the right wardrobe.
Whilst we prefer the black boots, the brown shade is so dark that it would work well with more formal attire as well as casual settings.
What To Expect From Budget Dress Boots
Although shoes are an essential commodity, they can also be particularly pricey. Unfortunately, we don’t all have the luxury to be able to splash out on new footwear for daily use or special occasions.
However, we understand the difficulty in being able to afford premium dress boots and much higher prices. Therefore, let’s take a look at what you can expect from dress boots under $100.
An major factor that contributes to pair of shoes’ final retail price is the raw materials used to make them. Hides of premium leather are very expensive as they’re graded and sourced from the best specimens. Similarly, each hide has graded areas with their own levels of quality.
Therefore, how do you make boots for less than $100? Usually, shoe manufacturers will rely on the deceptive wording of “genuine leather”. Whilst this does sound quite reassuring, genuine leather is actually one of the lowest grades.
Although genuine leather is perfectly adequate for smaller objects, it isn’t robust enough for footwear in the long-term. This is because the fibres are quite loose and will lose both their form and damage easily over time.
As an alternative to leather, some manufacturers turn to synthetic or “man-made” materials. However, cheaper man-made materials usually of poor quality and damage easily. They also don’t breathe and can be hazardous to your feet’s health.
Meanwhile, premium mad-made materials that cater to the growing aversion towards leather are very costly.
One of the most common techniques for attaching a shoe’s upper is achieved via welting. This is a term that applies to various techniques such as Goodyear welting or Blake stitching.
Whilst the Goodyear welt offers the best quality, it’s very time-consuming and impacts the final selling price. Meanwhile, the Blake stitch is faster but still quite expensive for sub-$100 boots.
Sometimes it possible to find cheaper boots that use both of these techniques. However, you’ll usually encounter cemented soles. This is the most common technique that’s used on cheap and athletic shoes where an adhesive putty-like paste will glue the two together.
Although cemented soles are perfectly functional, they don’t last for very long and the shoe will soon begin to split. Furthermore, welts allow shoes to be resoled. However, cemented soles can’t be replaced and the shoes must be thrown away.
Finally, the materials of the soles used on cheaper boots tend to reflect the price. Sometimes it’s possible to find leather soles with stacked heels. Nevertheless, most of them will be made from rubber.
Rubber is a broad term and there are high-quality specimens out there. For instance, Allen Edmonds often use Dainite rubber soles. However, these are made in the United Kingdom and offer both exceptional quality and long-term wear.
Generally, cheaper boots will rely on rubber as the main material for the soles. Sometimes they’re relatively decent quality but considering that the sole is cemented anyway, they might be on the cheap side.
Still, there are exceptions and sometimes cheap boots will go the extra mile on the sole quality given that it isn’t necessarily a huge impact on cost.
Are Sub $100 Boots Worth It?
Overall, we believe that footwear should be perceived as a long-term investment rather than a short-term expense. By spending a little more, your shoes or boots will last exponentially longer. Therefore, you benefit from a greater return and lower expense in the long run.
Of course, this all depends on the brand itself as sometimes you pay for the logo. Nevertheless, there are some makers that accurately price their footwear according to the time and cost for their production.
In order to be able to sell their footwear at low prices, manufacturers are obliged to cut corners and use cheaper methods and materials. Consequently, the shoes or boots will be good for a while but won’t necessarily last as long as something that’s only a little more expensive.
Whilst the dress boots above offer the best quality and variety that we could find on this budget, they’re not going to offer the same experience as boots under $200. In fact, by just increasing your budget by only $30, you’ll likely find some excellent footwear that will last exponentially longer.
As much as we stress the importance of spending a little extra to guarantee quality footwear, we realise that this isn’t always possible. Therefore, we put together this series of dress boot guides in order to cater to all budgets.
Yet, we feel that it’s important to stress the reality that dress boots under $100 won’t always offer the best value for money in the long term.
Now that you have read about the best men’s dress boots under $100, consider checking out some of our other related shoe guides:
- Best Men’s Dress Boots Under $200
- Best Men’s Dress Boots Under $300
- Most Comfortable Dress Shoes For Men
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"Great cheap boots! Some cool looking and stylish boots on this page that don't hurt my wallet!"Rating: 5.0 ★★★★★