KEEN Utility Chicago Boots Review | Comfortable Protection

KEEN Chicago Boots

Last Updated on August 16, 2022

Comfortable Keen Utility Chicago Boots Offers Several Options

We had already received one pair of KEEN Utility Chicago Boots when my pair arrived. It seems Keen was very excited to get several of our takes on this new design. I put them on with a mixture of skepticism and hope—I’ve enjoyed some Keen boots to no end and disliked others. While they all use the same last to make the inner shape of their boots, the mix of soft toe, composite, steel, and now carbon fiber makes for some variations in fit. If first impressions mean anything, I immediately felt comfortable in them and really liked the traditional look. I wanted to find a tactful way of saying that Keen nixed their traditional rubber toe overmold in favor of a traditional toe—and I hope they never bring it back.

Editor’s Note: Check out our best work boots review article for our favorite products for all applications.


  • Unbelievably comfortable
  • Three different toe/material options
  • Super-lightweight
  • Grippy, slip-resistant outsole
  • Left/right-specific carbon-fiber safety toes
  • Three options: Waterproof soft toe, ESD-rated, and waterproof EH-rated with removable metatomical PU footbed


  • Can’t really find any…

Stepping into a Cushy Boot

Look, if you think work boots have to be as tough as you are—we get it. But that doesn’t mean your feet should ever hurt after a full day’s work. With that said, having a more flexible midsole and a truly flexible, grippy outsole may also mean you need to replace your boots more often than you might like.

I’m OK with that.

For this review, I committed to wearing the Keen Chicago Boots every day for two weeks straight. My review pair featured the KEEN.DRY waterproof membrane and carbon fiber toe. These boots also come EH-rated (meeting ASTM F2412-17 and F2413-17 F I/75, C/75, MT/75, EH standards) to protect against contact with live electricity.

Keen ReGen midsole

When I first put these boots on, I literally sank into them. The heels have a nice spring in them, but they don’t stay compressed like memory foam. Rather, they cushion on impact and then put your heel back into place.

It feels pretty darn good.

I also noticed the outsole has some nice grip and flexes along with the midsole. That led me to wonder how well they’ll hold up over time to rugged use on rough and sharp surfaces.

Keen Chicago sole

Three Models of Keen Chicago Boots to Choose From

KEEN Utility provides the Chicago in three “flavors”. I like options as much as the next fellow, and they seem to have done a great job making some key features available but not mandatory. Check out the models:

KEEN Chicago 6″ Waterproof Boot (Soft Toe)

This basic Chicago 6″ waterproof boot features a soft toe and the KEEN.DRY waterproof, breathable membrane that lets vapor out without letting water in.

KEEN Chicago 6″ ESD Boot (Carbon-fiber Toe)

Instead of a waterproof leather upper, KEEN goes with a regular full-grain upper and adds ESD (Electro Static Dissipative) protection to help reduce excess static electricity by conducting the charge from the body to the ground.

It also features a carbon-fiber toe. The carbon fiber adds almost no weight and this boot lands just 1.6 ounces above the soft toe model.

KEEN Chicago 6″ Internal MET Waterproof Boot (Carbon-fiber Toe)

The third KEEN Chicago Boots option adds a flexible internal metatarsal guard. This PPE device provides protection by dispersing the weight of items that might cause injury should they fall, drop, or roll onto the top of the foot. The internal MET system might be preferable to many of the “English Knight”-looking models on the market today.

metatarsal guard

This boot style adds roughly 2.7 ounces of weight over the soft-toe version of the KEEN Utility Chicago. Finally, KEEN keeps the carbon-fiber toe and adds back the waterproof upper to round out this boot as the most protective of the bunch.

Wearing the KEEN Chicago Boots

With a proper fit, the carbon-fiber toe on the KEEN Chicago boots we reviewed did a good job of holding your foot comfortably in place. They didn’t slide around inside the front of the boot, nor did the additional MET protection feel weighty or intrusive on the top of my foot.

KEEN Utility Chicago Boots

Wearing them outside, in the shop on concrete for hours at a time, and on uneven terrain, these boots consistently demonstrated excellent grip and comfort. They remain extremely flexible—even with a carbon fiber safety toe box.

KEEN Utility Chicago work boots

The Bottom Line

I enjoyed wearing the Keen Chicago work boots. They present a nice medium-duty boot that emphasizes comfort, lightweight performance, and grip. You can lace up these boots and—almost immediately—know that you’ll love them enough for all-day use. The only downside is that the flexibility of the outsole makes them subject to faster wear and tear. While we don’t have many months of wear under our belts, expect to replace these yearly.

If you’re ready to give them a shot, you can pick them up on Amazon for between $170 and $180. Incidentally, KEEN makes these in Women’s sizes as well.

KEEN Utility Chicago Boots Features*

  • Left/right asymmetrical carbon-fiber toes (15% lighter than steel)
  • KEEN.DRY waterproof, breathable membrane
  • KEEN.ReGEN lightweight compression-resistant midsole provides 50% more energy return than standard EVA foam
  • Non-mutilating upper uses eyelets that won’t mar or damage surfaces they rub against
  • EH rated
  • ASTM/CSA-Certified, internal, flexible metatarsal guard
  • Contoured 90° heel (5/8″ Height) provides stability and helps “catch or lock” the foot in place
  • Nylon shank for midfoot support
  • Heat resistant, rubber outsole rated up to 572° F / 300° C


  • Available sizes: 7 – 15 (whole sizes only 12 and up)
  • Available colors: Brown (Tobacco)
  • Safety ratings*:
    • Meets ASTM F1677-96 MARK II Non-Slip Testing Standards
    • ASTM F2412-17 and F2413-17 M I/75 C/75 EH Standards or SD 100 Standards
    • Meets ASTM F2913-17 SATRA Non-Slip Testing Standards
  • Safety toe: None or Carbon-fiber
  • Materials:
    • Full-grain or waterproof leather upper
    • Oil and slip-resistant, non-marking rubber outsole
    • KEEN.ReGEN midsole
    • Moisture-wicking textile lining
    • Removable metatomical PU footbed
  • Weight (soft/ESD/MET): 23.3/24.9/26.0 ounces each
  • Price: $170-$180

Visit Keen Utility’s website for more information!

*specs vary across the three models, see the KEEN website for specifics

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