10 Best Winter Boots for Delivery Drivers in 2022

If you buy through links on our site, we may earn commissions at no extra cost for you. Learn More

Last Updated on March 31, 2022 by Jack Sanders

Delivery drivers often need to work in harsh conditions, and they need to wear a pair of winter boots that will keep them warm and dry.

Sadly, the available footwear choices are not the best out there.

We rounded up the best winter boots for delivery drivers to make your life easier, and they are all available right now.

Whether you want to keep your feet warm or prioritize safety, we’ll have a winter boot you’ll love to wear when delivering packages.


The Best Winter Boots for Delivery Drivers

Here’s a list of our top-rated winter boots for delivery workers.

  1. Thorogood Men’s Crosstrex Series 400g Insulated Waterproof Hiker Boots
  2. Timberland PRO Men’s Direct Attach Six-Inch Soft-Toe Boots
  3. Thorogood American Heritage 6” Moc Toe Work Boots
  4. KEEN Utility Men’s Philadelphia 400g Insulated Work Boots
  5. KEEN Utility Pittsburgh Steel Toe Waterproof Work Boots
  6. Timberland PRO Boondock Comp Toe WP Insulated Industrial Work Boots
  7. Timberland PRO Direct Attach Steel Safety Toe Waterproof Insulated Work Boots
  8. Thorogood V-Series 8″ 400g Insulated Waterproof Work Boots
  9. Timberland PRO Endurance Steel Safety Toe Puncture Resistant Work Boots
  10. KEEN Utility Davenport Composite Toe Insulated Waterproof Work Boots

1) Thorogood Men’s Crosstrex Series 400g Insulated Waterproof Hiker Boots

Features

  • Outsoles: Crosstrex 360 high traction outsoles
  • Footbeds: Cushioned PU footbeds
  • Waterproofing: Waterproof membrane

These Thorogood Crosstrex winter boots are one of the best options for delivery drivers. Their 400 grams of Thinsulate insulation guarantees their feet will stay warm when exposed to winter conditions.

Furthermore, they feature the so-called “Crosstrex 360” outsoles, providing excellent traction on whatever difficult surface delivery workers may encounter.

Even though they aren’t made in the USA, they’ve got surprising qualities, such as their waterproof membrane that keeps the feet dry without sacrificing breathability and abrasion resistant heels and toes to maximize the ruggedness of these winter boots.

Pros

  • Cushioned PU footbeds to maintain the feet comfortable at all times
  • 400 grams of 3M Thinsulate insulation to protect the feet from harsh winter temperatures
  • Composite shanks for improved stability of the boots
  • Crosstrex 360 high traction outsoles for all kinds of terrains
  • Flexible and durable Cement construction
  • Abrasion resistant heels and toes
  • Waterproof and breathable membrane wicks moisture and keeps the feet dry

Cons

  • Not made in USA

Customer Reviews and Scores

There are more than 235 reviews on Amazon.com about these work boots at the time of writing, and they have given them a 4.4 out of 5 rating on average. The reviews of this pair of work boots are positive overall.

Check price at Amazon.com

2) Timberland PRO Men’s Direct Attach Six-Inch Boots

Features

  • Outsoles: Oil resistant, nonmarking rubber lug outsoles
  • Footbeds: Open cell PU footbeds
  • Waterproofing: Waterproof leather

If you’re the type of delivery driver who despises having cold feet, these Timberland Pro Direct Attach boots are for you.

For once, they feature 400 grams of Termolite insulation, which keeps the feet toasty warm even in sub-zero temperatures.

They also have an oil and slip resistant outsole and waterproof leather to round out the boot’s features to maintain the feet safe (and also the rest of your body!).

When it comes to comfort, these delivery drivers shoes feature open cell PU footbeds and shock absorbing midsoles that diffuse the impacts and keep the feet and knees pain-free and fatigue-free thanks to the proper arch support.

Pros

  • Waterproof leather uppers that maintain the feet dry
  • 400 grams of Thermolite insulation for guaranteed warmth during the workday
  • Oil resistant, nonmarking rubber lug outsoles that provide good traction
  • Mesh lining that wicks moisture away
  • Open cell PU footbeds that fully cushion the feet
  • Nylon shock diffusion plates to keep the feet rigid when walking on unstable surfaces

Cons

  • Non over here!

Customer Reviews and Scores

There are more than 318 reviews on Amazon.com about these work boots at the time of writing, and they have given them a 4.7 out of 5 rating on average. The reviews of this pair of work boots are positive overall.

Check price at Amazon.com

3) Thorogood American Heritage 6” Moc Toe Work Boots

Features

  • Outsoles: Maxwear wedge outsoles
  • Footbeds: Cushioned footbeds
  • Waterproofing: None

These American-made Thorogood boots come with impressive comfort features that will make the lives of delivery drivers much easier. 

Their dual density footbeds cushion the base of the feet, allowing workers to complete their workdays without suffering from foot pain when wearing these walking boots.

Furthermore, they feature ergonomic midsoles and fiberglass shanks that work together to provide excellent shock absorption and torsional stability, which is essential for a better wearing experience.

When it comes to protection, these delivery work boots boast “Maxwear” outsoles, which offer exceptional traction on slippery and uneven surfaces. A feature that is critical for avoiding job injuries.

Pros

  • American made
  • Removable dual density inserts that easy the impacts of feet and knees thanks to its cushioning
  • Made with 100% durable leather that achieves a professional look
  • Cotton Drill Vamp lining maximizes breathability to wick moisture away in hot and humid conditions to avoid sweaty feet
  • Goodyear Welt construction guarantees durability
  • Maxwear wedge outsoles guarantee traction on slippery surfaces that delivery drivers might walk on
  • Fiberglass shanks for added structural stability of the boots

Cons

  • Tongue is a bit big, take that in mind when tying them to avoid leather buch up

Customer Reviews and Scores

There are more than 2,229 reviews on Amazon.com about these work boots at the time of writing, and they have given them a 4.5 out of 5 rating on average. The reviews of this pair of work boots are positive overall.

Check price at Amazon.com

4) KEEN Utility Men’s Philadelphia 400g Insulated Work Boots

Features

  • Outsoles: Oil, slip and heat resistant nonmarking rubber outsoles
  • Footbeds: PolyAer PU cushioned footbeds
  • Waterproofing: Keen.Dry waterproof membrane

If you’re searching for a reliable and comfortable winter boot for delivery drivers, you’ve come to the right place.

These Keen Utility Philadelphia work boots stand out thanks to their 400 grams of insulation, which keeps your feet dry and toasty while exposed to cold outdoor temperatures and other adverse weather conditions (i.e. rain).

They also have nonmarking rubber outsoles that are oil, slip, and heat resistant to keep UPS drivers from plunging face first onto the hard pavement.

Although they are a bit big, these insulated boots include cushioned “PolyAer PU footbeds” and PU flexible midsoles, which are essential in supporting the feet and giving them and the knees the rest they need to recuperate, which is crucial for delivery workers such as truck drivers.

Pros

  • Composite safety toe caps protect the toes without adding bulk or weight, which is key when carrying heavy loads
  • Keen.Dry waterproof membrane maintains the feet dry and wicks moisture away
  • Oil, slip and heat resistant nonmarking rubber outsoles that prevent delivery drivers from slipping and getting injured when walking on tricky surfaces
  • Nylon shanks that provide torsion stability and midfoot support
  • PolyAer PU footbeds and PU midsoles provide good shock absorption and decent arch support
  • 400 grams of Insulation

Cons

  • They’ve got a very large design

Customer Reviews and Scores

There are more than 163 reviews on Amazon.com about these work boots at the time of writing, and they have given them a 4.2 out of 5 rating on average. The reviews of this pair of work boots are positive overall.

Check price at Amazon.com

5) KEEN Utility Pittsburgh Steel Toe Waterproof Work Boots

Features

  • Outsoles: Slip resistant outsoles
  • Footbeds: Dual density compression molded Eva footbeds
  • Waterproofing: 100% nubuck waterproof leather

These Keen Utility Pittsburgh may be one of the most comfortable options for the delivery industry since they are popular among delivery drivers.

For once, they’re made with detachable metatomical EVA footbeds and PU midsoles that provide arch support, which is ideal if you’re on your feet all day.

Furthermore, these steel toe boots contain 100% waterproof nubuck high quality leather that looks amazing and keeps your feet dry while exposed to the elements, such as rain.

Steel toe caps and the slip resistant outsole are included in the boots to avoid injuries and offer the delivery driver an extra layer of protection that may be needed when they least expect it.

Pros

  • 100% nubuck waterproof leather looks great and guarantees durability
  • Manufactured with the Cleansport NXT technology that wicks away mositure and breaks down odor in sweat
  • Locking metal lace hooks provide the ability to achieve a perfect fit
  • Removable metatomical dual density eva footbeds guarantee comfort during the workday
  • Dual density compression molded Eva footbeds and PU midsoles
  • Steel toe caps prevent toe injuries from taking place

Cons

  • No cons over here!

Customer Reviews and Scores

There are more than 3154 reviews on Amazon.com about these work boots at the time of writing, and they have given them a 4.4 out of 5 rating on average. The reviews of this pair of work boots are positive overall.

Check price at Amazon.com

6) Timberland PRO Boondock Comp Toe WP Insulated Industrial Work Boots

Features

  • Outsoles: Slip resistant Thermal PU outsoles
  • Footbeds: Cushioned footbeds
  • Waterproofing: Waterproof full grain leather

These Timberland Pro Boondock work boots are the perfect winter boots for all tradesmen, including delivery drivers. 

Delivery drivers will no longer suffer from foot pains because of these boots’ dynamic anti-fatigue technology, which features cushioned footbeds and shock-absorbing midsoles.

Moreover, this heavy duty work boot has amazing features in terms of protection, such as:

  • Composite safety toe caps with entire toe protection to keep your toes from being smashed by falling packages.
  • Waterproof leather
  • Thermal PU outsoles for good traction on any surface

Pros

  • Nonmetallic composite safety toe caps that provide total toe protection without being bulky or heavy
  • Waterproof full grain leather
  • Thermal PU outsoles that are slip and oil resistant
  • Goodyear Welt construction that adds years of durability and makes the boots flexible
  • Dynamic anti fatigue technology with cushioned footbeds and shock absorbing midsoles
  • Fiberglass shanks for improved support and torsional stability
  • Exterior heel cups for added protection

Cons

  • They can be bulky for some workers

Customer Reviews and Scores

There are more than 9905 reviews on Amazon.com about these work boots at the time of writing, and they have given them a 4.6 out of 5 rating on average. The reviews of this pair of work boots are positive overall.

Check price at Amazon.com

7) Timberland PRO Men’s Hyperion XL Waterproof Work Boots

Features

  • Outsoles: Slip resistant Vibram outsoles
  • Footbeds: Dual density footbeds
  • Waterproofing: Waterproof leather

These Timberland Pro Hyperion work boots are unlike any other winter boot in comfort and protection.

They include Vibram outsoles, which are known to be slip-resistant on slippery surfaces, which is a vital guarantee for delivery workers who have to walk on slippery terrains regularly.

Furthermore, they are made of waterproof leather, allowing delivery drivers to work in bad weather without getting their feet wet.

Even though they take time to break in, they have a lot of excellent features like their Powerfit comfort system, which is made up of EVA midsoles and dual density footbeds and makes these boots very comfortable to wear, even for long hours, which is vital for truck drivers, to give you an example.

Pros

  • Slip resistant Vibram outsoles provide reliability and safety on slippery surfaces
  • Waterproof leather allows delivery drivers to work under the rain without getting their feet wet
  • Powerfit comfort system include dual density footbeds and shock absorbing EVA midsoles
  • Highly flexible and durable structure thanks to their Cement construction
  • Anti odor mesh lining that wicks moisture away

Cons

  • A bit stiff for the first few weeks

Customer Reviews and Scores

There are more than 2554 reviews on Amazon.com about these work boots at the time of writing, and they have given them a 4.5 out of 5 rating on average. The reviews of this pair of work boots are positive overall.

Check price at Amazon.com

8) Thorogood V-Series 8″ 400g Insulated Waterproof Work Boots

Features

  • Outsoles: Slip, oil and heat resistant outsoles
  • Footbeds: Removable shock zone PU cushioned footbeds
  • Waterproofing: Waterproof leather

These Thorogood V-Series are ideal for delivery drivers who have to work in chilly weather since they have 400 grams of Thinsulate insulation to keep their feet comfortable at all times.

Furthermore, they are made of waterproof leather, essential for preventing the feet from being wet while exposed to outside liquids.

Their V-series Chevron outsoles are slip, oil, and heat resistant, which is critical for delivery who want to feel confident when walking on slippery surfaces.

Last but not least, they have PU “Shock Zone” cushioned footbeds that give the feet the support they need to avoid long-term problems like plantar fasciitis.

Pros

  • Waterproof leather maintains the feet dry
  • 400 grams of Thinsulate insulation keeps the delivery man’s feet dry when exposed to winter conditions
  • Semi-oblique composite safety toe caps are both protective and ergonomic
  • Removable shock zone PU footbeds cushion the feet
  • V-series chevron outsoles are slip, oil and heat resistant
  • Goodyear Storm Welt construction is both durable and ergonomic

Cons

  • They’re on the larger side

Customer Reviews and Scores

There are more than 292 reviews on Amazon.com about these work boots at the time of writing, and they have given them a 4.3 out of 5 rating on average. The reviews of this pair of work boots are positive overall.

Check price at Amazon.com

9) Timberland PRO Endurance Steel Safety Toe Puncture Resistant Work Boots

Features

  • Outsoles: Slip, oil and abrasion resistant outsoles
  • Footbeds: Contoured single-density open-cell PU footbeds
  • Waterproofing: None

Here’s some insider knowledge: Timberland PRO Endurance is one of the best winter boots for delivery workers on the market.

These boots have superior comfort features, such as:

  • Contoured single density open cell PU footbeds that fully cushion the feet to maintain them relaxed during long drives, which is particularly good for truck drivers.
  • Shock absorbing midsoles that delivery excellent arch support
  • Moisture-wicking mesh linings with antimicrobial properties

Even though they are a little hefty, these steel toe reinforced boots contain protective features like slip, oil, and abrasion resistant outsoles that prevent significant injuries when delivery drivers need to walk on slippery or uneven surfaces.

Regarding the level of protection these boots provide for delivering packages, they have steel toe caps, puncture resistant plates, and abrasion resistant toes, making them,  by far, one of the most protective choices of this article.

Pros

  • Abrasion resistant toes for increased protection
  • Puncture resistant plates guarantee underfoot protection
  • Electrical hazard protection
  • Steel toe caps
  • Slip, oil and abrasion resistant outsoles guarantee high tracion on slippery surfaces
  • Antimicrobial mesh lining for odor control
  • Cement construction reduces break in time and maximizes durability
  • Contoured single-density open-cell PU footbeds and midsoles provide excellent feet support
  • Fiberglass shanks that substantially improve stability

Cons

  • They are a touch heavy

Customer Reviews and Scores

There are more than 3088 reviews on Amazon.com about these work boots at the time of writing, and they have given them a 4.6 out of 5 rating on average. The reviews of this pair of work boots are positive overall.

Check price at Amazon.com

10) KEEN Utility Davenport Composite Toe Insulated Waterproof Work Boots

Features

  • Outsoles: Oil and slip resistant nonmarking rubber outsoles
  • Footbeds: Cushioned footbeds
  • Waterproofing: Keen.dry waterproof membrane

With their uncomplicated mixture of features, these Keen Utility Davenport could be the best winter boots for delivery drivers.

I mean, they come with 400 grams of Keen.Warm insulation, which maintains the feet at a nice and toasty temperature when exposed to cold winter conditions.

Moreover, they have composite safety toe caps and slip and oil resistant outsoles, making them very protective.

Lastly, they have electrical hazard protection, which you might think it’s a bit extra for, let’s say, a FedEx driver, yet it has proved to be an essential feature to avoid electrocution when exposed to live wires.

Pros

  • Composite safety toe caps are as protective as steel toe caps yet 10% lighter
  • Keen.dry waterproof membrane is responsible for keeping the feet dry when exposed to exterior liquids and also for wicking moisture away
  • Oil and slip resistant nonmarking rubber outsoles that allow delivery workers to confidently walk on slippery surfaces
  • 400 grams of keen.Warm insulation protects the feet from exterior cold temperatures
  • Electrical hazard protection

Cons

  • No cons over here

Customer Reviews and Scores

There are more than 272 reviews on Amazon.com about these work boots at the time of writing, and they have given them a 4.5 out of 5 rating on average. The reviews of this pair of work boots are positive overall.

Check price at Amazon.com


What Are The Best Winter Boots for Delivery Drivers Overall?

Timberland PRO Men’s Direct Attach Six-Inch Boots

Because of their various qualities, I rated these Timberland Direct Attach boots as the best overall for delivery drivers due to their many features, such as:

  • 400 grams of Thermolite insulation that keeps your feet warm in cold weather
  • Oil-resistant, non-marking outsoles that provide excellent traction on slippery and uneven surfaces, which delivery drivers frequently encounter – Open-cell PU footbeds and shock-absorbent midsoles

Anyway, if you want to read the entire review, just click the button below.

Go to Review

What Are The Most Comfortable Winter Boots for Delivery Drivers?

Timberland PRO Men’s Hyperion XL Waterproof Work Boots

Of all the winter boots reviewed in this article, the Timberland Hyperion is the most comfortable.

Delivery drivers can keep their feet cushioned and supported on all terrains thanks to their Powerfit comfort system, including dual-density footbeds and shock-absorbing EVA midsoles.

Moreover, the boots feature slip-resistant outsoles and waterproof leather, making them an excellent footwear option for delivery workers.

Go to Review

What Are The Best Women’s Winter Boots for Delivery Drivers?

Timberland PRO 6IN Direct Attach Women’s Winter Boots for Delivery Drivers

The MaxTRAX tread outsoles, which provide optimum traction on slippery surfaces, are essential features that make these Timberland Direct Attach work boots the best footwear option for female delivery drivers.

They also feature steel toe caps, which prevent the toes from severe damage caused by falling heavy packages.

Last but not least, cushioned footbeds and shock-absorbing midsoles can help female delivery drivers avoid foot exhaustion and other issues by keeping their feet relaxed.

Check price at Amazon.com


Quick Comparison

NameOutsolesFootbedsWaterproofing
1. Thorogood Men’s Crosstrex Series 400g Insulated Waterproof Hiker Boots
Crosstrex 360 high traction outsolesCushioned PU footbedsWaterproof membrane
2. Timberland PRO Men’s Direct Attach Six-Inch Boots
Oil resistant, nonmarking rubber lug outsolesOpen cell PU footbedsWaterproof leather
3. Thorogood American Heritage 6” Moc Toe Work Boots
Maxwear wedge outsolesCushioned footbedsNone
4. KEEN Utility Men’s Philadelphia 400g Insulated Work Boots
Oil, slip and heat resistant nonmarking rubber outsolesPolyAer PU cushioned footbedsKeen.Dry waterproof membrane
5. KEEN Utility Pittsburgh Steel Toe Waterproof Work Boots
Slip resistant outsolesDual density compression molded Eva footbeds100% nubuck waterproof leather
6. Timberland PRO Boondock Comp Toe WP Insulated Industrial Work Boots
Slip resistant Thermal PU outsolesCushioned footbedsWaterproof full grain leather
7. Timberland PRO Men’s Hyperion XL Waterproof Work Boots
Slip resistant Vibram outsolesDual density footbedsWaterproof leather
8. Thorogood V-Series 8″ 400g Insulated Waterproof Work Boots
Slip, oil and heat resistant outsolesRemovable shock zone PU cushioned footbedsWaterproof leather
9. Timberland PRO Endurance Steel Safety Toe Puncture Resistant Work Boots
Slip, oil and abrasion resistant outsolesContoured single-density open-cell PU footbedsNone
10. KEEN Utility Davenport Composite Toe Insulated Waterproof Work Boots
Oil and slip resistant nonmarking rubber outsolesCushioned footbedsKeen.dry waterproof membrane

Must Have Features of The Best Winter Boots for Delivery Drivers

Winter boots must have certain features to be suitable for delivery drivers. So let’s have a look at them.

Slip Resistant Outsoles

Delivery drivers are accustomed to walking on various types of terrains. Unfortunately, some of these surfaces are too slippery to safely walk on, causing them to trip and fall onto the hard concrete.

I advise delivery drivers to get slip-resistant outsoles on their next pair of work boots.

This will assure them that they will have an excellent grip on all surfaces and that no severe injuries will occur.

Safety Toe Caps (Optional)

Even though this is not the primary concern when choosing safety footwear for delivery drivers, we can note that these workers are responsible for lifting hefty packages that could collapse and crush their toes.

This is why I chose a few of the previously reviewed work shoes with safety toe caps, which will give complete foot protection in the toe box area.

So, if you’re the type of delivery driver that accidentally lets heavy packages fall on their toes, I’d recommend a winter boot with protective toe caps.

Insulation & Waterproofing

Delivery drivers are not only exposed to low temperatures but also to sudden rainy weather when working in winter conditions.

This is why I believe it is critical to get winter boots with good insulation and waterproofing, as both will keep your feet dry and toasty when working outdoors in the harsh winter.

In terms of insulation, I prefer 3M’s Thinsulate, although there are other excellent options available, such as Thermolite insulation.

Reliable Construction Method and Materials

Do you enjoy wasting the money you earned as a delivery driver?

No? Well, me neither, which is why I’d say that durability should be your priority when looking for the best winter boots for delivery drivers.

So, how do you go about doing this?

Simply ensure that your boots are:

  • Made from high-quality materials (100 percent full grain leather)
  • Built using tried-and-true methods (i.e. Goodyear Welt method)
  • Made by reputable companies (i.e. TImberland, Keen Utility)

Cushioned Footbeds & Shock Absorbing Midsoles

And what about comfort?

Don’t worry; I haven’t forgotten about those delivery workers that suffer sore feet at the end of their workdays. 

When shopping for your next pair of winter boots, I’d recommend looking for two features:

  • Shock-absorbing midsoles
  • Cushioned footbeds

These qualities will give your feet the arch support they require so that your feet and knees do not suffer the brunt of the impact when walking on hard and uneven surfaces, which should make any boot perfect for all day wear.


Frequently Asked Questions

The following are the most often asked questions concerning the best winter boots for delivery drivers, including the answers.

How to maintain the best winter boots for delivery drivers?

The process of maintaining leather winter boots is pretty simple, you just have to do the following:

  • Dust off the boots with a brush
  • Wash and rinse the exterior of the work boots with saddle soap
  • Let the boots dry for an hour (or for as long as they need it)
  • Apply a thin layer of leather conditioner and let it work for about 30 minutes
  • Remove excess conditioner with a clean cloth
  • Buff the boots with a clean brush

And that’s it, your boots should be looking as good as new now!

What are the best boots for a UPS driver?

The UPS driver is a vital part of the UPS supply chain. They are responsible for delivering packages to their destinations on time, doing heavy physical labor. UPS drivers typically work in a truck, van, or SUV.

Due to the nature of their jobs, their winter boots should have the following features:

  • Sturdyness: UPS drivers will be using their work boots for 8 to 12 hours on a regular shift for driving, walking on pavement or mud, hell, even for climbing stairs. In that context, you’ll need a boots that will sustain the beating without issues.
  • Slip resistant outsoles: Slippery driveways, stairs and other wet surfaces are very common surfaces on which a UPS driver walks. This is why they should get work boots with slip resistant outsoles that will guarantee traction on these areas to avoid serious injuries from happening.
  • Black or brown leather: As a company policy, all UPS drivers should wear black or brown leather boots.

In that context, I’d say the Timberland Direct Attach should be a nice option for them as they hit all the previous points. Again, you can read the full review here.

What features should the best boots for driving long distances have?

Driving lengthy distances has the disadvantage of being quite exhausting. It can also be risky, as avoiding accidents requires high attention. Additionally, the driver may become exhausted and angry, leading to severe accidents. This is why I believe the best boots for driving long hours should have features that bring the maximum comfort possible, such as:

  • Cushioned footbeds
  • Shock-absorbing midsoles
  • Fiberglass shanks that provide torsional stability and good ankle support.
  • Lightweight and flexible construction methods (i.e., cement construction)

In that context, I believe the KEEN Utility Pittsburgh boots might be a really nice choice for a delivery guy who drives long distances.

Author: Jack Sanders
Hey there, I’m Jack, founder and editor in chief here at WorkBootsGuru.com. After my best friend spent hundreds of hours trying to convince me, I decided to take control of my life and finally got to make this site. I’m on a mission to share my insider tips with every man who has a skilled trade job.

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.