Just by making simple fashion decisions, you can boost your self-esteem, make you more productive and improve your career opportunities. Every week, I help 1,000+ men make the most of their wardrobe with fashion tips to upgrade your life.
I’m an outdoor style aficionado. I’ve been collecting for years, and I’ve built an online business based on my love of classic outdoor clothing.
Old Woolrich, vintage L.L. Bean, salty Abercrombie & Fitch from the ’60s, patched-up cotton canvas jackets, field pants, W.C. Russell hunting boots—yes, please!
The materials are all natural, typically wool or cotton. The cost of classic pieces is usually very accessible if you’re willing to search.
The level of comfort is hard to beat, and the performance—in the city or the woods—is spot on.
So, let’s build an outfit!
Footwear
W.C. Russell Moccasin Zephyr Boot
I always start at the feet and work my way up. For classic footwear, my default is W.C. Russell Moccasin boots.
Russell Moccasin has been making outdoor boots and shoes in Berlin, Wisconsin, for 126 years. They’ve put boots on explorers ranging from Charles Lindbergh to Mr. Indiana Jones himself, Harrison Ford.
My Russell boot of choice is the Zephyr Boot. It’s highly water-resistant, roomy, and tough enough for the woods, yet dressy enough for the city.
A handmade American boot will set you back about $1,000, so if you want to save, start searching your preferred online marketplace for bargains.
The best part of the Russell line is that they can be repaired and resoled, lasting essentially forever if you take care of them.
Keep yours clean and conditioned to keep them in great shape.
You can view the entire Russell Premium Build line on my website: www.cwoodcockandco.com.
Pants
A Pair Of Well-Loved Dickies Cotton Canvas Carpenter Pants
For a classic field pant, I lean into basic cotton canvas trousers. I prefer a roomier seat and wider leg—plenty of room to move in the field and space for my boots at the cuff.
For the past 15 years, I’ve worn Dickies 12oz cotton carpenter pants in duck brown, cutting off the hammer loop as soon as they arrive.
Lately, I’ve been buying these pants on eBay to score that perfect pre-fade from day one.
A solid pair that will last you years can be picked up for about $25.
Belt
Kingfisher Leatherworks Plantation Cut Belt
I make belts, so I wear my own—I haven’t bought one in years.
For this particular look, I recommend a 1.5” - 2” Garrison Belt in full-grain leather with a solid brass buckle.
You can’t go wrong with this classic style, and expect a quality belt to outlive you.
W.C. Russell also makes a fine belt, available via my website.
Expect to spend about $100 on a handmade-in-the-USA belt.
Don’t sweat the initial acquisition cost as the per wear over time cost will be pennies.
Shirt
Vintage Abercrombie & Fitch Viyella Shirt For my field look, I’ve loved classic Viyella shirts for years.
The Viyella wool/cotton blend is a sure-fire winner when the temperature drops.
Vintage A&F Viyella shirts will last for years and are still relatively inexpensive on the vintage market.
New versions are available from several online retailers. Just remember to wash cold and hang dry to extend their lifespan.
Jacket
Vintage Drybak Field Jacket I’m a huge fan of the vintage cotton canvas field jacket. These come in dozens of variations from numerous makers.
Ralph Lauren has produced versions of this American classic for years, and the RL versions perform as well as they look.
Other great options include L.L. Bean, vintage A&F, American Field, Filson, and more—often available online at reasonable prices.
For something contemporary, check out the Tensaw Jacket by Tom Beckbe in Birmingham, Alabama.
Cap
I’m partial to the classic long-bill fishing cap for the field. Hemingway wore this style in the 1930s, and it looks as sharp today as it did 80 years ago.
Papa Nui Cap Co. and Quaker Marine Supply both produce excellent versions in several variants.
In 2024, I collaborated with Papa Nui on a design called the Blue Marlin, which I wear religiously in the field.
Bring any—or all—of these elements into your autumn style, and I guarantee you’ll find yourself reaching for them again and again.
Get into the field!
Do You Need My Help?
Have you ever found yourself staring at the closet not knowing what to wear?
Do you need help with coordinating pieces?
Do you constantly struggle putting an outfit together and want to turn that confusion into confidence?
Then let's talk about how we can improve your look.
Just by making simple fashion decisions, you can boost your self-esteem, make you more productive and improve your career opportunities. Every week, I help 1,000+ men make the most of their wardrobe with fashion tips to upgrade your life.
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