The Jefferson Derby

The Jefferson Derby

Ink Black / 8 / Wide
$185.00
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The Jefferson Derby
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The Jefferson Derby

$185.00
✅ Premium Full-Grain Leather
✅ Zero Drop, Wide Toe, Flexible
✅ All day natural comfort
✅ Free exchanges
✅ 30 Day money back guarantee

Sizes are US. Size down if a half size.

ColorInk Black
Shoe size
Shoe fitWide
Description

The Jefferson Derby - Our barefoot Derby made from premium full grain leather. We only work with tanneries that hold a Gold rating from the Leather Working Group (LWG)—the highest environmental standard in the industry. LWG-certified leather means responsible water and energy use, controlled chemical management, and reduced environmental impact.

Details
  • Premium Full Grain Leather
  • Wide Toe
  • Zero Drop
  • Faux Heel
  • Flexible
  • Slip On
Product Video

Barefoot Dress Shoes for Professionals

Traditional dress shoes cause joint pain, poor posture, & toe squeezing.


OAKA's give you all the comfort & benefits of barefoot shoes while remaining stylish for the office and special occasions.

As Featured In

Free Your Feet

Our aim is modern comfort. We redesigned the dress shoe from scratch to be wide toe & zero drop allowing your toes to splay and your gait to strike naturally.

Timeless Style

We created special cutouts in the outer sole to mimic a professional heel without actually adding any height. We combined this with classic styles to provide comfort and a clean look.

These cutouts double as outlets for our hidden tread system, normally found in sneakers, that helps prevent hydroplaning.

Premium Leather

We only use full-grain leather and only work with tanneries that hold a Gold rating from the Leather Working Group (LWG)—the highest environmental standard in the industry. LWG-certified leather means responsible water and energy use, controlled chemical management, and reduced environmental impact.

Freedom Through Natural Movement

Zero Drop

OAKAs have a zero drop inner sole allowing you to walk as if barefoot. This means your toes and heel sit at equal height to each other to the ground.

This improves posture and aligns your gait.

Wide Toe

Our shoes come with a wide toe box allowing your toes to splay as they naturally would helping to improve balance and reduce foot pain.

Flexible Sole

Our whole shoe is soft and flexible for comfort and foot mobility, unlike rigid traditional dress shoes.

Anti Slip

We also made OAKAs anti-slip through a hidden open tread outer sole that reduces hydroplaning.

Similar to sneakers however we use our faux heel cutout to allow water to displace without having to show the treads on the outside.

Customer Reviews

Overall rating: 4.8 / 5 from 105 reviews.

Nicely made and comfortable. I wish the shape could be a bit more like the Adams- these super-wide toe boxes just can’t help but looking a bit like “special” shoes!

The Jefferson Derby

The initial size was a little small but having received the next size up, all was good. Applying the shoe can be a little 'different' as the opening is relatively small and the tongue can get dragged in as your foot goes in. However, once you get a technique going it is a lot easier. Once you get p and walking it is like wearing a pair of comfortable slippers. Magnificent!

The Jefferson Derby

Excellent shoe - it has a wide toe-box for natural foot expansion and zero heel drop simulating barefoot walking. The non-slip outsole is excellent, and the footbed is very flexible. (I now have three pair)

The Jefferson Derby

Excellent shoe - it has a wide toe-box for natural foot expansion and zero heel drop simulating barefoot walking. The non-slip outsole is excellent, and the footbed is very flexible. (I now have three pair)

The Jefferson Derby

I ordered two pairs. The first pairs that arrived were too big. The return was super simple. The shoes are little challenging to get on. The insoles are comfortable but really grab socks when trying to put your foot in. I would suggest unlacing one of holes prior to initially putting them on. My only complaint with the shoe is the heel, I cannot wear dress socks with them. I have to wear athletic socks for the heels to be comfortable for me.

The Jefferson Derby

Shoes are great! Just as described and as they appear in pics! Very satisfied with them!

The Jefferson Derby

Love the look and always loved the feel of Oaka shoes.

The Jefferson Derby

Very comfortable and well made shoes

The Jefferson Derby

I love walking in them and they look conventional enough that I don't seem to get attention from anyone (the goal). The heel back was actually wearing into the back of my heel though. I ordered "Heel Grips Liner Cushions Inserts for Loose Shoes" through Amazon, and that saved the day. Maybe I could have used a half size smaller shoe? I don't think you offer half sizes though. Still, I like the shoes after my modified heel back intervention.

The Jefferson Derby

Comfortable shoes with plenty of toebox space

The Jefferson Derby

They feel great, only thing is that the back cuts into your ankle, so it need to be broken into order thick socks. Other then that no complaints

The Jefferson Derby

Elastic laces coupled with fabric on tongue are a problem preventing the foot from easily getting into shoes. The tongue sticks on the socks fabric necessitating loosening the top lace by pushing out of its hole.

The Jefferson Derby

Great for long commutes. Comfortable the whole time.

The Jefferson Derby

Works well for business casual outfits. Very wearable daily.

The Jefferson Derby

Easy to slip on and go. Great for busy mornings.

The Jefferson Derby

Comfort over everything here. Very noticeable difference.

The Jefferson Derby

Great for business casual settings. Not too formal.

The Jefferson Derby

Very lightweight and flexible. Perfect for long commutes.

The Jefferson Derby

These feel closer to sneakers than dress shoes. The flexibility makes a huge difference. I don�t feel fatigued after work.

The Jefferson Derby

Not ideal for black tie. Great otherwise.

The Jefferson Derby

Feet feel healthier wearing these. Much less strain.

The Jefferson Derby

Easy to wear all day. Good flexibility.

The Jefferson Derby

Too wide for me. Comfortable though.

The Jefferson Derby

Good for walking around the city. Flexible and easy.

The Jefferson Derby

Good breathability throughout the day. Feet stay cool.

The Jefferson Derby

I use these mostly for commuting and office wear. They perform well in both. Comfort is the biggest benefit.

The Jefferson Derby

I bought these for work travel. They pack easily and feel great walking through airports. Definitely a practical upgrade.

The Jefferson Derby

These are surprisingly comfortable. Much easier on my feet than leather shoes.

The Jefferson Derby

Comfortable right out of the box. No adjustment needed.

The Jefferson Derby

The material feels breathable and flexible. Good for warmer days. My feet stay comfortable throughout.

The Jefferson Derby

Comfort is excellent for a dress shoe.

The Jefferson Derby

The wide toe box makes a difference. No more pinching.

The Jefferson Derby

Very lightweight compared to traditional options. Walking feels more natural. I don�t notice them much during the day.

The Jefferson Derby

Feels natural when walking. Much better than stiff shoes.

The Jefferson Derby

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Frequently asked questions

What is the return & exchange policy?

We accept exchanges and returns within 30 days of receipt. You can see full details at our Returns & Exchanges Page.

Are the insoles removable?

Yes, our insoles are removable. Replace them with any others you prefer.

What is the stack height of the shoes?

Stack height is about 11mm.

What if I'm a half size?

We suggest sizing down. But no worries, you can exchange for free to make sure you get the right size.

When will I get my order?

There are two shipping options. Our standard option shipping times typically takes 3 to 5 days while our expedited takes 2. International orders typically can take up to 2 weeks to arrive. All orders usually ship out of our warehouse within 48hrs of purchase.

Can I use my own laces?

Yes, the laces are removable and you can use regular laces with your OAKAs.