Wayward Staff’s Top Picks

Words by Chris Zimmerman

If there’s one thing you can say about the staff at Wayward, aside from being super friendly, knowledgeable, and generally good looking, is that they get their hands on a lot of product. Pretty much all of it actually. From knowing the in’s and out’s of all the latest gear, to helping customers find their perfect match, this team is a go-to for everything product related. Looking for a little gift giving help from the pros? Our Seattle, Bellevue, Chicago and HQ staff took some time from their busy schedules to highlight their top gifts for the season. After seeing, touching and trying on as much gear as they have, it can be hard to pick a favorite, but that’s what had them do anyway. Check out our full Staff Picks collection for even more top ideas from our team. 



Wayward Bellevue

My pick for the holidays is the Yellow 108 Dylan Fedora because this hat can do it all! The Dylan comes in many colors, is super stylish and outdoorsy, and does great in rain or shine! With its timeless look, this is the gift that will keep on giving… to your wardrobe at least!




Wayward Bellevue

The Bootleg Botanicals Old Fashioned Cocktail Infusion Kit is perfect for that crafty friend, a foodie brother-in-law, a new couple or just to have on hand for any extra Christmas Eve guests. Add a bottle of whiskey and it’s a great gift for under $60!





Wayward Bellevue

My pick is the Red Wing 6″ Classic Moc Toe boots. I need good support for being on my feet all day and the wedge style sole makes all the difference. I get no pain and no fatigue. With their durable leather uppers they’re great for trucking around the city and the countryside. Plus you get timeless style that only looks better with age and a construction that will last a lifetime.






Wayward Bellevue

My pick is the beautiful Copper Plated Growlerwerks uKeg 128oz growler. My husband and I love to stop by one of our many local breweries to fill her up with 128 ounces of liquid gold—an IPA. This baby can keep beer carbonated for weeks, but we never have it for that long. These uKegs are sure to make you the life of any holiday party and are great for gifts for parents, friends or even yourself.




Wayward Chicago

My pick for the season is the Filson women’s Moorcroft jacket. This badass jacket is warm, flattering, and protected from the elements. I may or may not have already snagged one up for myself.





Wayward Bellevue 

There’s nothing better to take off the edge like a hot, stiff morning coffee from the Yeti Rambler 20 Oz Tumbler with a little extra love from the Roark Runaway Flask. Take your time and wake up slow because your drink will stay piping hot, no matter the pace. Whether heading to the mountains or out to the in-laws, this morning pair will keep anyone warm and jolly all winter.



The Snackler

Wayward Marketing

My pick for the season is the Carhartt WIP Small Bag because it’s the perfect size to stash snacks. I like that it clips to your bag or belt so snacks are never out of reach and always by my side. It might even be worth buying two of them: snacks on each hip or as a backup snack reserve for an extra long day.





Wayward Seattle

My holiday pick is the Cotopaxi Bataan Fanny Pack, because if you are going to get a pack for your fanny, it had better be a statement piece. It’s also a great alternative to purses and backpacks if you’re just running around town or trying to take minimal items on an adventure.





Wayward Seattle

This season, I like the Lomography Simple Use Camera in purple. It’s like a time warp to the days before cell phone cameras. Also, with the filter options, it’s like having old-school Instagram at your fingertips, but you end up with a tangible memory to hold onto.





Wayward Chicago

My pick for the holidays is the Filson men’s Insulated Jac-Shirt because of its excellent durability and weather resistance for the coming winter months. The insulation provides warmth, and the waxed canvas exterior makes sure it’s long lasting.





Wayward Chicago

My pick would have to be the Carhartt WIP men’s Michigan Chore Coat! Not only for the timeless style but the design of the jacket itself is a perfect fit. I personally find jackets like these thrifting all the time, and I own one already, but it’s incredibly difficult to find one new. With that in mind, I really love the idea of getting a new version and making the wears my own!




Wayward Seattle

My holiday pick this season are Red Wing boots! Specifically the Clara Boot. From durability, comfort and style, Red Wing boots have everything I need. These boots are a great way to complete your look and take your outfit from a low 6 to a solid 10. Come try them on to find out for yourself!






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