Customer Reviews Timberland PRO Five Star Regent

These are the most comfortable boots I've ever worn in my life, they feel a little big for Timberlands because the Pro's I always wear fit a half a size small, but these run a little big which is great because I usually wear a 16 or a 15 wide but these are great. I want to order a second pair but they're not in stock.

A casual shoe with enough appeal to pull off in dress situation, the Timberland Pro Five Star does well to provide amazing comfort and fit while still maintaining a level of support and style we all look for.

They are just as advertised. Extremely comfortable. I have not tried them yet during inclement weather but they should be great.

These are very similar to the slip-on type Chukkas that Timberland used to make under its general (i.e. not "Pro") brand. They seem to try to chase the styling of the moment there but these are cleaner and more classic looking. I just wish they made them in brown as well as black.

These were purchased to replace an older pair, quality and workmanship were much better on the older ones. Originals made in Wash. new ones in China and it shows; would not buy again.

The boots were fine at first, but widened out to where 3 socks needed to make them fit right. After 2 months I gave them away.

This boot runs a 1/2 size big, so please consider that when ordering. It is a great looking, comfortable, classy boot. I would recommend this item.

Like others have said, buy a half size smaller. I have another pair of Timberland boots, and I still had to buy small. At first, I wan't crazy about the slip-on fit, bit adding an insole made it feel perfect.

These are the most comfortable boots I've ever worn. Originally ordered 9 and 9.5 (which is my regular size). Both were too large. Returned and ordered the 8.5 which was perfect. Seems Timberland's sizes are bigger than marked, or perhaps other brands are smaller than marked.

I bought this for my husband to replace an old pair of boots. He loves them. They are comfortable and stylish. Good arch support and roomy around the toe area. This was definitely a good buy.

I had read some review that said that this boot runs a little large, so I sized down and got the 11.5 wide -- smart choice. As it's a slip-on, my heel does slip a little bit inside of it even though I'm normally a 12 US/45 EU with wide feet, but it's nothing that I'm worried about -- it is a slip-on, after all! It's incredibly comfortable and has been supporting my fat feet for an entire month now, and not once after any 10-hour days have my feet felt sore in these. Pair with some padded socks for maximum comfort in a nicely dressy, well-constructed boot!

Love these boots. Wear them for work daily and they still feel great. I would recommend these boots to everyone.

Tighter in the toe box than my Timberland PRO workboots of the same size - specifically there is a squeeze across the top of my toes. However, it has been decreasing with wear and otherwise they are just as comfortable as my workboots.

Okay, so these boots are not shoes. If you have never had your foot properly sized for work boots, cowboy boots, western footwear, etc., then you need to do that first. For instance I wear a 9.5 in sneakers and dress shoes since high school. In this boot, I wear a 8.5EE. They fit perfect. All difficult manual labor and heavy lifting and bumping and kicking that I do every day at work goes unnoticed by the boot. They don't scuff or scratch. They're light and comfortable. They pop on easy and I can kick them off with my other foot. Tiny rocks get stuck in the sole and will scratch a wood floor, but it's a small price to pay for such a great boot. I wear them 5 times a week with jeans, khakis and work pants. Worth every penny you pay and then some. Don't even bother looking at other brands that look the same. Don't forget...know your boot size before ordering.

I was very skeptical of ordering shoes on the internet. Zappos return policy and ratings made it an easy choice. After reading the reviews of this boot I thought I would give it a try. Delivery was fast and easy. About the boots. I work in retain and am standing on my feet all day, with other boots I have bought my back is aching at the end of a long shift. These boots are AMAZING they feel like I am wearing slippers and MY BACK DOESN'T HURT AT THE END OF THE DAY. I wasn't sure if I would like the slip-on low cut of the boot but after wearing them everyday for almost 3 weeks it is the most comfortable and natural feeling shoe/boot I have ever owned. From the moment I put them on they fit and feel perfect. I am going to get another pair for normal wear and keep these for work. Do yourself a favor and get these boots.

These are a great investment. I'm in the restaurant business and have had these shoes for three months and they still look new. I haven't oiled or polished them either. I only wish they came in brown.

I am a huge fan of Timberland products. That being said, these run a half size too big. I wear a 10 1/2 and had send them back and ordered a 10. The Size 10 fits like a glove. Great looking shoe and very comfortable. This is the second time that Timberland has been off on sizing. Wish they could make up their minds on the sizing scale. Last time on other PRO series boot they were a size too small.

I love the shoes, I've owned them before and knew they run one size too big. I always get compliments on them and they make you an inch taller! Very happy with the purchase.

I'm very pleased. They do run a half size large, and I learned this by exchanging a pair of 12's for 11.5's. They are super comfortable and can be worn all day, they look sharp, and they slip on and off pretty effortlessly (great for TSA checks). The slip-resistant sole is good for around the city/suburbs. I wish they made one in brown and with hill-scrambling tread.

Nice looking boot. Perhaps a little bit larger than size, might consider 1/2 size smaller when ordering. Otherwise fits and looks great.

Looked all over my metro area for a professional work boot with a little style. No one stocked them. Found 4 excellent options on Zappos. These shoes have been very comfortable and provide me the level of sophistication I was seeking.

Nice looking boot and it fit well from the day I put it on. It is easy to put on with the helpful loop on the back of he boot. Very good none skid surface on the sole of the boot

I am a woman and I got these in a mens 8 when I wear between a 9 and 10 in womens. They fit me like I like, so true to size. Great work shoe. Truly non slip. Super comfortable even after 10 hours. They look good too.

Great shoe, very comfortable. I can wear this all day. The sole has cushion and it comes with an extra insole. The shoe looks good, but wears a little large. Get exactly the size you wear or maybe half size small. I usually wear a wide shoe, but this one is just wright due to fitting a bit larger than usual. The stretch elastic on the is great, allowing you to put on and take the shoe off very comfortably.

Man, Zappos is great. I ordered (5) pair of shoes before deciding on this boot (which is also a fantastic product - very comfortable and rugged) with free shipping both ways (including returns). The service is always superb. In fact, I will never go to a shoe store again.