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Casual Luxury: The Bennett Winch Briefcase

October 3rd, 2017

The latest offering by Bennett Winch is heavy on quality and style

There are no shortage of bags and briefcases out there these days. In fact, new brands seem to pop up every time you refresh your browser. One of the few that have distinguished themselves from the herd – at least in our opinion – is Bennett Winch.

You may recall our review of their stylishly rugged canvas duffle bag last winter and today we’re taking a look at a brand new product in the Bennett Winch line-up: The Brief.

bennett winch briefcase review


What distinguishes Bennett Winch are the high-quality materials they use. A 24 oz. British dyed and bonded waterproof cotton canvas is brushed and therefore not only has an elegant look, but an amazing feel as well.

That quality extends to the premium full grain leather trim and handles. You’ll also find solid brass hardware, which is welded in London, and YKK golden brass zippers. You might not think of cotton canvas as being particularly luxurious, but in this case, it is and then some.

bennett winch briefcase review

| WEARING | Michael Andrews Bespoke jacket, Brunello Cucinelli shirt, Yves Saint Laurent pants, Breifcase c/o Bennett Winch, Seaward & Stearn x HSS pocket square, Oliver Peoples sunglasses, Rolex watch, Loafers c/o Allen Edmonds | PHOTOGRAPHY | by Rob McIver Photo


The Bennett Winch Brief isn’t the largest briefcase, nor is it the smallest. From the outside, it’s just about the perfect size and its slim profile gives a chic and modern look. Inside, there’s a padded sleeve that holds up to a 15″ laptop, three interior pockets for various items and one external zip pocket that fits a phone, wallet or passport.

Design & Style.

I find the Bennett Winch Brief to be mostly well designed. There’s a leather panel on the back which can be slipped over the handle of a suitcase, making this briefcase an ideal travel companion. There is one detail that I have a love-hate relationship with: the leather hood.

The leather hood does not fasten down, it’s held in place by the handles when you carry it. I love this detail from a design standpoint – it covers the zipper and gives the bag a sleek, minimalist and modern flavor – but it makes it somewhat frustrating when trying to get items in our out as it continually flaps back into place and gets in the way.

bennett winch briefcase review

The Bennett Winch Brief really shines from a style perspective. The addition of the leather flap, while admittedly annoying, makes it less casual than a Filson Original Briefcase, while its cotton canvas body makes it less formal than an all-leather number. What that means is you get an incredibly versatile briefcase that could easily be an everyday carry.

bennett winch briefcase review

Overall Impression.

Personally, I love the style and look of this briefcase. It’s sleek and modern, yet still very classic. This isn’t an everyday bag for me, however. As I do a lot of commuting in and out of the city, I really need a larger outer pocket to quickly stash (and have easy access to) my phone, wallet, notebook, and so on. For me, the Bennett Winch Brief is a stylish situational carry rather than a workhorse briefcase.

Finally, let’s talk about price point. At $650 GBP (that’s roughly $870 USD), we’re talking a substantial investment. The saying goes, “you get what you pay for” and while that isn’t always true, in this instance it certainly is. I would recommend the Bennett Winch Brief for someone looking for a briefcase that would work in between their formal leather brief and a more casual twill.

bennett winch briefcase review

Thanks for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style

Brian Sacawa

Brian Sacawa is the Founder of He Spoke Style and one of the original men’s style influencers. Since 2013, his goal has remained the same: to provide men the advice and inspiration they need to dress well, develop their personal style, and gain more confidence. Brian’s interest and passion for men’s style and luxury watches has led to his writing for The Robb Report, The Rake, and Sotheby’s and he has been quoted on menswear in publications such as The New York Times, The Wall Street Journal,, Brides Magazine, and the Huffington Post. He lives in the woods north of Baltimore with his wife, Robin, kitties Nick and Nora, and German Shepherd/Collie mix Charlie.

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