Frye Prison Boot Review

Frye Prison Boot black

Do you need a nice pair of above-the-ankle boots? You are in the right place! If you read any Frye Prison boot review , you will see that this pair of boots will set you back a good amount of money.

Therefore, you do not want to buy these shoes when you are in a hurry. You want to be sure that this product is worth all the money that you will pay for it. If the features and the durability justify the price, well, you can go ahead and buy.

If looks matter to you, you can go for this pair of footwear. They do indeed look unique from the soles to the upper parts. They come in stonewash leather, in all sizes and they mostly come in black or brown color. From the looks alone, you can tell that these boots are different from many others that we have reviewed here. However, looks alone cannot tell you much. That is why you need to see the features and specifications.

Frye Prison boots features & Specifications

First, perhaps we can start with what these boots are best suited for. They are great for motorbike riding. They are also good for regular wear. You can wear them with a pair of jeans or even dress pants and they will look awesome on you. Some people even wear them for outdoor recreational activities such as hiking.

Design and build quality

These shoes are designed to reach a couple of inches above the ankle. They are full lace up boots and they come in different shades to suit the needs of different people.

The shoes are designed to last a long time. The hardy leather upper plus the thick sole (which we shall look at next in detail) are built to last. Going by the longstanding tradition of the John A. Frye Shoe Company that has been in operation since 1863, you can only marvel at the many years of experience that have gone into making these shoes.

These shoes come in neutral colors. Therefore, they match with just about any color of pants. This kind of versatility makes the boots endearing to any man.

You may get lucky and order their 150th anniversary edition boots. When you get them, they will look distressed, rough and a bit aggressive. They will look as if a railroad worker has worn them for years. This is intentional, but if you do not like the overly rugged look, you can tone it down using some clear polish.

Upper and sole

The upper part of this footwear is made of leather. Going by their name, these shoes were made for prison system and so they have a prison number stamped on the side. They are tough and resilient and the leather does not sustain scuffs easily.

Image of Frye Prison Boot

The shaft measures 3 inches or thereabouts. Therefore, if you will be wearing the shoes to a place where you need more ankle support, perhaps you had better look for another boot. The inside of the shoes feels quite comfortable. The leather has been carefully treated and the shoes lined in the interior to make your feet feel comfortable even if you wear them for a long time.

You can apply oil on the leather to make the boots water-resistant. However, please note that just like any other leather shoes, if you wade in water for too long, the leather will eventually be soaked. However, they do hold their own against showers and splashes very well.

Leather has a quality of breathability. Even this one is not any different. When you wear the shoes in summer, they will allow air in and your feet will not sweat too much.

The upper part of the shoe is mounted so skillfully on the sole. Our guess is that should there be the need to replace the outersole, it will be very easy to remove this one.


The Frye Men’s Prison Boot is made with a synthetic sole. We do not know why they used this sole and not the combination of leather/rubber as they have done with their Men’s Bowery Combat or the complete leather sole on their Frye Men’s Tyler combat boots.

Synthetic soles have the benefit of being waterproof. They do not soak or allow water to seep in. You can rely on this outer sole to keep you completely dry.  The sole is thick, such that even if you walk on pebbles or on rocky ground, you will not feel these rocks pressing into your feet.

The way the sole is joined to the shoe it is not going to be any trouble to remove it when it is worn out and replace it with another. In another Frye Prison Boot review, we saw a customer saying that their shoes have gone through three sole changes.

You will eventually have to change the sole because it takes all the beating, being in contact with the ground and carrying your weight. However, with good care and maintenance, the upper part of the shoe will remain intact for long.


The shoes come with stock insole. You do not need to remove this one because it is comfortable. You will have to break in the shoes for a short period, but the longer you wear the shoes, the more the interior conforms to the shape of your feet.

Please note that these shoes are quite roomy on the inside. Therefore, if you feel like adding another insert, you can go right ahead. For most people though, the stock insert is more than enough and they do not need to add anything else.  Just listen to your feet.

Size and fit

These boots are made for men. Therefore, they come in men’s numbers and width sizes. All customer reviews say that these boots run large, some say they run true to size. However, it is recommended that you order a half size down so that they can fit you snugly.

These boots need to be broken in. This is no surprise because most leather boots require to be broken in. However, you will be happy that these ones require just a short time and so you can wear them daily soon after you unbox them.

From checking with different people, the basic rule of thumb when ordering Fryes is to order a half-size down. Therefore, if your wear size 11.5, order size 11, or the shoes will be too big for you. If you have wide feet, you will love the comfortable and roomy interior of the boots. The toe area looks slightly boxy, but only slightly. This enhances the appeal of the boot, making it look much better on and off your feet.

Lace and Tongue

For boots that you plan to wear almost every day in a week, you have to ensure that the tongue is good. The tongue is the extension of the boot that insulates your foot from the pressure exerted by the laces. At the same time, the tongue prevents debris from getting inside your shoes.

With these shoes, you can walk with them on bushy trails or areas with pebbles and none of them is going to find its way inside your shoes. Besides, the tongue is wide enough to keep your foot covered completely. One downside with many boots is that their tongue slips to one side most of the time. However, with Frye Prison boot, the tongue stays intact.

The laces are made of leather. They can get a bit nasty if they absorb water and when they are new, they tend to be a little tough to tie up. However, they will soften with time as you continue using them. They also take some work to lace up. With good care, the laces should last as long as the upper part of the shoes.

Frye Prison Boot Pros

  • Built to last a long time, usually need a couple of sole changes as years pass
  • Rugged finishing for the upper leather part gives the shoes more masculine look
  • Require minimal to zero break-in period
  • These boots are good to wear with any pant color
  • They can be used for a variety of purposes including riding motorbikes
  • The are comfortable on your feet and require no custom inserts
  • You can wear these boots with a dress suit
  • The leather requires minimal care and maintenance, mostly colorless polish
  • The soles are thick to offer more protection


  • A simpler lacing system would have been better than the leather laces
  • They require a break-in period albeit a short one


These boots will cost you between $200 and $380 on different online marketplaces, but prices do change from time to time. Considering the durability that you will get from these boots, the price range is quite fair and some customers even say they have bought up to three pairs.

Who should buy the Frye Prison Boot?

Basically, these are men’s shoes. That is why they look so rugged and they are only available in either black or brown color. Whether you are looking for dress boots, bike riding boots or casual wear boots, they will meet your needs perfectly.


Having read this Frye Prison boot review, you can now decide whether you want it or not. If you get it, you will be assured of ultimate protection for your feet, stylish design and comfort even if you have to wear them all day long.

However, they do need some tender loving care from time to time. You should clean them and polish them with neutral polish so that the scruffs in the leather can be toned down some. As far as stonewash leather boots go, these ones are excellent.