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The Gladiator Chelsea Boot in Honey on model

The Gladiator Chelsea Boot

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Kennedy in Grey side view
Kennedy in Grey top view
Kennedy in Grey back view
Kennedy in Grey bottom view

The Kennedy Shoe in Grey (Last Chance, Final Sale)

993 reviews
Regular price $250 $175
(Last Chance, Final Sale)

The product is currently out of stock.

Free shipping in the U.S.

Meet the Kennedy. Our favorite thing about this shoe is the versatility. Wear it with slacks, wear it with jeans, wear it to work or a dinner party. The Kennedy will quickly become your new go-to. This is a captoe lace-up with Blake construction. It has a reinforced stacked leather sole with rubber inserts for extra durability. The wool flannel is made in Italy and then shipped to our factory in Spain. When we initially previewed the shoe it became a fast favorite and we couldn't be happier to finally have it available. 

Product Details
  • Wool Flannel from Italy
  • Standard D width
  • Handcrafted in Spain
  • Blake Construction (resoleable)


Customer Reviews
4.8 Based on 993 Reviews
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Michael Z.
United States
Comfortable & versatile

My second pair of Taft shoes...they are a bit tighter than the Saint boots, but still very comfortable. These shoes literally go with everything (except shorts) - I've already received tons of compliments. Highly recommend.

TAFT The Kennedy Shoe in Grey (Last Chance, Final Sale) Review
Lazaro S.
United States United States
Another Perfect Product

This is the second time I've gotten the Kennedy in gray. This has become a staple in my shoe collection. I like how you can dress the shoe up or down. I absolutely love this shoe.

Jordan M.
United States United States
1st order review

So here's the deal. Came across an aesthetic style of shoe (kennedy in stripes) and liked them very much so and they were on sale. Sizing scale told me to go a size 10 (I wear a 10 in timb boots) but I wear a 9 or 9.5 in shoes or dress shoes (wide). Since this was my first pair and a last chance deal I couldn't return, or re fit the style. After unboxing I aboslutely fell in love. The quality of the shoes and box to the shoe horn and even the bags the shoes can travel in were the utmost quality I've ever experienced with a sophisticated men's dress shoes brand. I tried them on and they do fit.(with some room). They are comfortable. However I wish from my own experiences I wish I could have found out prior if a 9 would have been a better fit. Granted a 9 wasnt avail. A return or exchange for resize wasn't available. They don't offer "half" sizes. But I can't wait to wear these shoes.out to dinner with a few friends and can't imagine the compliments I'll receive. Maybe I'll play around with the sizes for the next order but I'll what, if you read this long, I can't wait to buy another. The shoe addiction is gonna be real.

Charles F.
United States United States
Great pair of Shoes

In typical Taft fashion, the unboxing was magical and the shoes look great and are well built. They were very snug compared to other Taft size 11s, but they loosened up to size when after wearing them a few times. I've gotten lots of compliments when wearing them around town.

Alex A.
United States United States
Love These Shoes

Stumbled upon this brand and thought The Kennedy Shoe looked really nice. Bought them on Final Sale and hoped they would fit since they don’t allow returns on Final Sale products. They fit perfectly, are very comfortable, and look great! The shoes have minor differences between them, but they aren’t very noticeable unless you sit and stare at them. The size guide worried me a bit, but it was accurate. I will be buying more shoes and boots later on.

Find My Size

Sizing Guide

How To Measure

For fail proof measure please take the time to measure your foot.
  1. Put a piece of paper on the ground next to a wall
  2. Standing firmly on the piece of paper with your heel slightly touching the wall, mark the paper where your foot is the longest (most likely at the tip of your big toe)
  3. With a ruler, measure the distance from the wall to the mark on the paper (indicating the longest part of your foot)
  4. Take that measurement and match it with a measurement in the “Inches” column in the size chart.
    • Wear socks when measuring your feet
    • Measure your feet at the end of the day, as your feet tend to expand throughout the day
    • Measure both of your feet, as one may be bigger than the other

Sizing Guide

All Taft shoes are designed to match standard US dress shoe sizes. However, to ensure the perfect fit, please make sure:
size d
All our shoes are standard D width. If you have wide feet, please select next size up.
size inbetween
If you wear in-between sizes, please size down for Taft boots and shoes.
size sneakers