Timberland Wodehouse Cap Toe Oxfords Review

Timberland Wodehouse Cap Toe Oxfords Review

Timberland Has a Dress Shoes Line?

Timberland Wodehouse Oxford

This is the Timberland Wodehouse Cap Toe Oxfords review. It’s hard to come across a vintage looking Oxford dress shoe that works for both your business suit and your everyday casual outfit. The Timberland Wodehouse Cap Toe Oxford fits the bill. What looks like some engineer’s worn out dress shoes brings you one the most unique shoes currently out there.  I recently bought two styles of the Wodehouse and I can tell you they are some of the most comfortable shoes I’ve owned. Here’s a few reasons why.

Timberland Wodehouse Cap Toe Oxfords

Timberland Wodehouse Cap Toe Oxfords

One of the biggest highlights about this classic shoe is the larger toe-box area at the front of the shoe. Most people will usually feel pretty cramped around the balls of their feet due to the snug width of most dress shoes initially. However, the Timberland Wodehouse Oxford fixes that by giving you just the right amount of space to wiggle your toes around without keeping your foot from flopping around. A flexible strap connected with the tongue of the shoe helps to keep your feet comfortably in position. With this in mind you’ll probably notice that a size down will fit you better as the shoe runs a tad bit on the larger side. The first thing you’ll notice after trying on the right size? Instant comfort. 

Another major highlight about the shoe is the outsole of the outsole of the shoe. As you’ll notice it doesn’t come with much of a back heel like most wingtips and oxford dress shoes do. As a result, your foot will lay much flatter and closer to the ground. I think this is what adds to the comfort level of this shoe. When you follow the back part of the shoe up to the front you will also notice that it curves upwards, producing an almost see-saw like affect as you stroll around in the shoes. This however puts less strain on the back of you heel and divides up the pressure, while putting the majority of your weight in the balls of your feet. The result is less strain and more comfort for the long periods of time you’ll find yourself spending in these shoes each day.

Timberland Wodehouse Oxfords

Timberland Wodehouse Oxford Strap

Looking at the shoe from a distance there will probably be a few thoughts that come up in your head. One will most likely be..these look worn out or too distressed. Not so much the story here. The leather is of Horween quality, some of the best quality leather that you can still get today. The thinness of the leather has also been craftily weathered down to give it its softness and customized look. When you actually try one on in person you’ll see just how genuinely soft the leather is on the outside and inside. Each shoe being finished differently will also give it a unique feel and look that fits to your liking.

As for the worn out look, it may not seem like a style for you at first, but it grows on you the more you wear it around. You’ll see why so many magazines list it as both a business and casual shoe.  Some detailed aesthetics were also brought into mind when designing the shoe. Looking at the cap toe lining you’ll see that its not fully complete on either shoe. 2/3rds will stretched across on one end with the other 1/3 finishing the cap toe lining on the other. A surprisingly nice effect Timberland brought with this shoe.

Timberland Wodehouse Cap Toe Oxfords

Final Thoughts?

You might be thinking, “What do I dress these guys up with?”. It’s actually quite simple. As mentioned before it can float both ways with your wardrobe. Dress it up with a business suit and feel confident in sticking out with a unique and crafty looking shoe that still shows off professionalism. Dress it down with your casual after work attire or going-out night attire. Jeans and khakis will all work with this shoe, especially the black. No matter what situation you wear them in you’ll always be found to carry a strong sense of fashion.

Last thought that may still make you question these shoes..Are they resoleable? That answer is a yes. Take them to your local cobbler and you’ll be right back to the first day you bought them. Check them out here on Timberlands website.

Timberland Wodehouse Cap Toe Oxfords

Timberland Wodehouse Cap Toe Oxfords Sole

Anson Zong-Liscum

Lots of things interest me in this complex world. The things that have the biggest influence on my life however would be the creative world of fashion, mesmerizing art, the life-changing effects of traveling, the global world of cultural connections, and the way marketing effects all of us. It's an interesting world out there. Hit me up if you live in my world.


  1. I’m thinking of getting some of these Timberland Wodehouse Oxfords, but the size I tried on was snug. The salesman said these will definitely stretch out and give me more room. Since this post is a few years old, can you provide any real-world insight into how much they relax over time?

    • Hey Corey,

      Since these shoes do not make half sizes and run pretty big for standard sizing, I would definitely go down to the next whole size. I bought a nine and should’ve went with an eight. The leather is not super thick like many other dress shoe brands and so they will stretch easier compared to other leather shoes you own. As long as they’re “comfortably snug” I would recommend the size down. They are some of my favorite shoes. Let me know if you have any other questions!

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