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Review: These Madewell Sneakers Are the Greatest Everyday Men’s Shoes I’ve Found This Year

Shoes might be one of the most inadvertent lines of communication into a person’s true sense of style. Even beyond style, the shoes a person chooses to wear can paint a picture of their overall character. Look at somebody near you and think about the cleanliness of their shoes, the brand they’re wearing and the style they picked — there’s a story to be told.

There was a point in time where I thought Vans Slip-Ons looked stupid. Fast forward about four years and I owned, seriously, 13 pairs of Vans Slip-Ons. Today, as a person to detested chunky-soled sneakers, I’m beginning to come around to them. I broke the ice this past summer with the Ventura T-Toe Lace Up from Stacy Adams, and recently, discovered this Madewell sneaker called the Kickoff Trainer, and it might be one of the greatest sneakers I’ve found this year. 

For eight years, I worked in various shoe stores selling, well, various shoes. That’s probably where my shoe “collection,” we’re going to optimistically call it a collection, stems from. Of the 20-or-so shoes I’ve collected this year, nothing has surprised me more than this pair of vintage-inspired running shoes. 

Here’s why. 

Madewell Kickoff Trainer Sneakers


Madewell Kickoff Trainer Features

The Madewell Kickoff Trainer is a retro-style running shoe that, while not suited for running anymore, makes for a great casual sneaker for daily wear. They’re incredibly comfortable, boasting Madewell’s ultra-supportive MWL Cloudlift insoles, and had an overall break-in time of, in my case, under an hour.

Madewell Kickoff Trainer Sneakers

Despite the volume of raw material, these Madewell sneakers were designed as sustainably as possible. The Kickoff Trainer is a mixed-media shoe. The canvas and rubber outsole are made from recycled material and the suede was sustainably sourced. The leather used was also sourced from a tannery that scored a Gold Rating from an organization called Leather Working Group (LGW), whose mission is to bring awareness and accountability toward sustainably produced leather.


How Does the Madewell Kickoff Trainer Fit?

With sizes ranging from 7M-13M, finding the best fit is simple. In the case of these Madewell sneakers, my Brannock size, a 10.5M, fit perfectly. They fit great with any type of sock, but would also do well sockless, if that sort of thing is your bag, baby.

Do note that this particular type of style, along with many other retro-inspired running shoes, tend to run generously width-wise. This just means that more shapes of feet will also have an easy time fitting into these sneakers. 

Madewell Kickoff Trainer Sneakers


How to Style These Madewell Sneakers

Madewell men’s clothing is no stranger to us at SPY. One thing to love about Madewell Men is the neutral, but versatile colors the brand leans into every season. We’re talking the entirety of the greyscale, muted yellows, understated blues, masculine greens and all while finding a way to make beige not so boring. 

The Moon Rock Multi colorway in this Madewell sneaker focuses on the textural convergence of beige and grey with punches of black throughout. The beauty of styling a sneaker with a neutral color palette is that you don’t need to keep the style in-house. Today, as this story is being written, I’m playing on the black in the sneaker with a pair of black Levi’s 511 slim jeans, a black Levi’s western style shirt and a simple white t-shirt from Everlane.

Madewell Kickoff Trainer Sneakers


The Verdict: Should You Buy the Madewell Kickoff Trainer Sneakers?

Again, as somebody who was vehemently against wearing chunky-soled sneakers as recently as a year ago, I’m telling you this is one you need to consider. 

Given this Madewell sneaker’s easy break-in time, the generous width and the three versatile colorways, the Kickoff Trainer can easily become a twice or thrice-a-week sneaker in every man’s wardrobe for at least the next year. 

Yes, trends come and go, but the chunky sole has been popping up for close to four years now, meaning it’s likely to stay for a little while longer and you’ll get more use out of it.  Plus, at $98, and for a sneaker that features recycled materials, it’s right on par with the other best sneakers for men we’ve found this year. 

Madewell Kickoff Trainer Sneakers


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