Guy Style // Red Wing Boots

November 22, 2012
Hey all – Mr. Pepper, here.  Given that we’ve been faced with some slightly inclement weather over the past few weeks, I thought it might be time to address the importance of all-weather boots in today’s Guy Style feature.  See below for my tips plus more photos, and feel free to let me know if you have any menswear-focused style questions in the comments at the bottom of this page.

Over the past few posts, we’ve discussed several closet staples for the stylish gentleman in your life, and a decent pair of utility boots is no exception.  Ideally, they’re something that he can wear quite a bit during the colder half of the year, and they especially come in handy for those times of tromping through rain or snow.

While it’s true that a classic pair of Duck Boots will keep your feet warm and dry, they can look a bit silly if you aren’t hunting, doing farmwork or attending an equine sporting event.  I’ve found that something like this pair of Irish Setter Red Wing boots can be the perfect solution, and they fill the gap in nearly any shoe rack quite nicely.  They’re perfect for all types of nasty weather, yet they don’t look out of place if I wear them out with Mrs. Pepper on a chilly evening.


The trick in selecting your own pair of all-weather boots is to find a pair that not only suits your style, but that can clean up well when needed.  While I usually wear my boots with denim, I don’t mind pairing them with the occasional wool pant to create an unexpected touch to the outfit.  To ensure I don’t look like I just stepped off the construction site, I also make an effort to add the necessary “third piece” on the top half, and if you’re opting in for the same, be sure to pick something that fits well and elevates the look (think cashmere sweater, not zip-up hoodie).  As you can see here, I’ve kept my shirttails un-tucked for that artfully disheveled look, but you can do whatever you please.

Finally, a well crafted pair of all-weather boots calls for close attention and care.  Make sure to have cans of saddle soap and mink oil on hand (they make great stocking stuffers!) to ensure that the leather on your boots stay clean and healthy throughout the brutal winter.  Taking these simple, yet necessary precautions will mean that they will surely last for years to come.

Top to Bottom:
Shirt – Baltic stripe Thomas Mason, J. Crew
Sweater – Cashmere V-neck in heather toffee, J. Crew
Denim – Garment-dyed 484 Jean, J. Crew 
Boots – Irish Setter Red Wings

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  • Reply NadineisthatU November 22, 2012 at 8:01 am

    Mr. Pepper, one of the things I am putting in the men and boys stockings is a hand body lotion I got samples of last year. It is Dial for Men, NutriSkin Ultrahydrating hand and body lotion. It has magnesium, miacin, amino acides, and Vitamin A, C, and E. Even got some for my working hard hands. The women’s version does not contain these ingredients, so I went for the men’s which I can attest to. My shoes are always taken care of, having been an event rider, and it being absolutely necessary to take care of your tack and your boots. Have a great holiday.

  • Reply Isa November 22, 2012 at 9:03 am

    I love guy style. Love the layers here and the rolled jeans – and, of course, the boots.

  • Reply mike crawford November 22, 2012 at 1:41 pm

    G$! – I think my Redwing purchase, inspired by your Irish Setters, was one of my best ever…still loving them so much…miss you guys!

    • Reply Jessie Artigue November 26, 2012 at 2:54 am

      Perfect, Mike! We miss you guys, too. :) Hope you and the fam had a fabulous Thanksgiving! Come see us in NYC!

  • Reply Aymara November 24, 2012 at 6:36 pm

    We love Mr. Pepper! My guy treated himself to a pair of these last year and they have been a great investment!. I’m going to suggest this nice autumnal color palette you’ve tried here. Thanks!

    • Reply Jessie Artigue November 26, 2012 at 2:54 am

      Oh, yay! Glad he can be of some inspiration for your guy. :) XOXO

  • Reply Isabel November 9, 2018 at 10:02 pm

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