Urban Shepherd Boot Review

Let’s be honest, if you have a friend who wants a pair of boots under $300, chances are you either tell them to save up or you tell them to buy a pair of Red Wings. Sure, there are other options technically such as Wolverine, Chippewa, Thorogood, and even Allen Edmonds depending on your style. However, none of those brands have matched Red Wing in popularity or even in overall consistent quality. Not that I don’t like Red Wing, but it is a shame that I haven’t had any other brands to recommend to people in the highly important sub-$300 price point.

Fortunately, there have been a few boot brands recently that have tried into this very market. Today, I will be taking a look at one of those brands. Urban Shepherd boots are made in Portugal, which originally sounded a shrill alarm in the back of my head. Portugal makes fine products, but it is often used as Europe’s go to place for denim and boot brands to outsource their production at lower prices. Thankfully, Urban Shepherd’s founder is in fact Portuguese himself and therefore the production is not outsourced to a different country, something that I can very much appreciate. Moreover, these boots are said to be uniquely Portuguese or at the very least, inimitably Iberian.

To give full disclosure, these boots were sent to me for review by Urban Shepherd. I have stated and will continue to state the fact that no human can be completely unbiased. I will still try to be objective as possible, but please do keep in mind that these boots were not purchased by me with my own money and this may affect my review.

I don’t know if it’s movies or just my imagination, but these boots do have a very European work boot vibe to them. They make me think of French or Iberian work boots that I feel like I’ve seen somewhere, but cannot exactly place. The specific pair that I have is the “Country” boot which is their standard six eyelet lace up boot, but with the addition of a cap toe. It is a polarizing design for sure. The heel is not a woodsman, but it is a little higher than standard. The mini lug sole is not my favorite, but it works decently well here. Red stitching and red or white cotton only laces are interesting choices that I personally like, but a lot of people do not. Even the shape of the boot is abnormal. It looks quite short and stubby. The toe is not upturned or bulbous, but the boots appear quite stout and wide.

Personally, I really love this look overall. They certainly do not look like service boots, Iron Rangers, or anything else. They stand out. In my eyes, they stand out well. That early-mid century European work boot vibe they have is really pleasing to me. I also think that the red stitching helps them stand out. With that said, a significant amount of people have commented to me that they despise the way these boots look or don’t like some of the specific details. In fairness, I agree that Urban Shepherd should make a slightly more standard looking boot given their mass appeal price range or at the very least, should offer models that have leather laces and white or tonal upper stitching instead of red if for no other reason to appeal to more people.

Styling is not something that can be objectively measured, however. What is more objectively impressive, however, is the list of features these boots have for their price point. Currently listed at $275 with a coupon that takes them down below $250, these boots include features such as actual Vibram soles and are fully lined with calfskin leather.  They also have brass hardware, genuine leather insole, midsole, and heel stacks as well as a cork footbed and natural waxed flesh leather from a Portuguese tannery.

The leather is something else that I personally like, but may not appeal to everyone. It’s a nice mid brown color that is nicely waxed and matches well with the natural finished midsole and red upper stitching. Being waxed flesh, it should age very well, especially if you are someone who loves patina. Waxed flesh is also a great choice for a less expensive boot as it can age really nicely without being vegetable tanned and hides boring/lack of grain or imperfections better than a regular smooth out leather. However, I again have to point out that it is a fairly unique choice that a lot of people may not like and Urban Shepherd would probably be wise to add some more options if for no other reason than to have… well, options.  Recently, they did announce that they will be producing some boots in black leather which is a nice start, but still more options, and non-red stitching with leather laces would be nice too.

For me, comfort is excellent on these boots with only one issue. As with styling, this is extremely subjective as every foot is different. One interesting note about the comfort that I noticed was that the footbed of these boots is extremely soft and even quite squishy feeling from the first wear. I have talked to other Urban Shepherd owners and they mentioned this was the case for them as well. Hopefully this does not come at the price of durability and long term comfort, but I have no reason to suspect that as of now. On the plus side, this makes the boots impressively comfortable out of the box, especially in the foot bed.

Break in was overall quite easy, but not perfect. The reason for this is that one issue that I alluded to in the previous paragraph and that is the fact that sizing on these boots is as confusing as a healthy cheeseburger. I am a 10.5 D on a Brannock device and was told by Urban Shepherd to take an 11 in their boots, but this is still slightly too small on me. This did cause them to rub the sides of my feet a little too much for the first week of wear, but this has since disappeared. Now the boots are quite comfortable, but I can tell that I probably would be slightly better off with a half size larger boot. I hope the Urban Shepherd team can figure out their own sizing soon, because this is something they should already have understood better. I am not the only person who received boots from them who had sizing issues. With that said, their customer service appears to be quite excellent and responsive so that is a big plus. The end result of this is that I would personally suggest taking one full size up from your Brannock size, but take this with a grain of salt.*

Now we can move on to what I believe is the most important aspect of any boot and what can most objectively be measured- construction quality. Here, the Urban Shepherd boots are a mixed bag. One massive positive is that the finishing on the heels/edges/outsole is seriously good, especially for the price. In fact, the finishing here is far superior to my Viberg boots which cost more than three times as much. The overall finishing is quite good and they do appear to have put some real effort into it, even waxing down the upper stitching which helps hide or prevent frayed or loose threads from showing up. The sole stitching is fairly even and neat, though not extremely dense. The upper stitching is also fairly neat, though not especially dense either.

On the downside, there are some wonky stitches here, especially where the vamp meets the upper. There are some ugly, overly-long stitches here that look quite unsightly. Worst of all, there is a broken stitch on one of the uppers. On one hand, this is in an area with quad stitching so I’m not worried about long term durability. On the other hand, this is really not good and does not speak well of the brand as it is the only pair in my collection with this issue. My guess is that the waxing down of the upper stitching hid this issue from the quality control team which is a shame. I did mention issues like this to Urban Shepherd and they did mention that they would address this, so hopefully it will be taken care of in the future.

In terms of construction, I am split. They are both better and worse than my Red Wings. Where the construction and finishing is great, it walks all over Red Wing, but the worst issues are worse than either of my Red Wing boots. Objectively, this is tough to call because there are objectively better and worse aspects to the construction and finishing with these boots when compared to Red Wing. As far as my opinion goes, I would say that Red Wing is a safer choice as of now, but Urban Shepherd has the potential to beat them in terms of overall finishing quality in the future.

Overall, I am not entirely sure how to feel about these boots. Despite some construction and sizing issues, I like them. They are a mess of contradictions these boots. The insoles are super comfy, but the sizing is confusing. Some aspects of the finishing are stellar, but other construction aspects need serious improvement at least in terms of consistency. The boots are fairly unique in terms of design and style, but they are also quite polarizing and will definitely not appeal to a lot of people. While I do like the look, I have to also point out that they are far from my favorite in terms of looks. However, this is also unfair on Urban Shepherd because I obviously prefer engineers and lace up boots with woodsman heels that take inspiration from Pacific Northwest Packer boots instead of European work boots.

Bringing price back into the picture definitely helps. At under $250 right now, I would say that they are worth the money. If I was buying my first pair of good boots and my budget was under $300, I would definitely save my money until I could buy exactly what I wanted which is exactly what I did do. My first pair of quality casual/Amekaji boots were John Lofgren engineers and I did not regret going so high end from the get go.

If you told me I absolutely had to buy something under $300, then I would either buy a pair of Red Wing engineers just because I love engineers so much or a pair of Urban Shepherds, though probably one of their pull on boots simply because I am more of a laceless boot guy.**If the brand can clean up their construction a bit and figure out their sizing, I think they have a chance to be a real player in the sub-$300 boot market. However, only time will tell and I think they do still need to make a few more moves before they are going to start challenging Red Wing, but I hope they do. The more competition there is at this price point, the better for boot lovers. To answer my own question at the beginning, I would recommend Urban Shepherd to someone looking for boots under $300, but not instead of Red Wing, only alongside them at this point.

*You should take ALL sizing advice with a grain of salt. I have never EVER seen people able to agree on how any boot- from Viberg, to Lofgren, to Road Champs, to Red Wings should be sized and that’s because ALL FEET ARE DIFFERENT. Do NOT take any one person’s sizing advice as gospel, including mine.

**I chose to review this lace up pair because I already have so many pull on boots in my collection.