It’s winter – almost.  That means a certain type of guy will be making an appearance over the next few weeks: the urban adventurer.  Unlike the gentleman to the left, they’re not out climbing a glacier, hoofing it up K2 or trekking the Appalachian Trail. No, they’re just going to work.

These are the guys who look like they’re in the process of summiting Everest but in reality strolling up Capitol Hill and then catching the elevator to the second floor.

You’ve probably seen him too; out driving in a vintage AA yellow Range Rover Defender – complete with exhaust snorkel – that has never seen so much as a gravel side street.  His laptop is housed in an expedition quality backpack and he weathers the occasional shower in a Patagonia monsoon-proof rain shell.

Now, while I enjoy poking a little fun at the Urban Adventurer, it’s all in good humor.  I think most of us have exhibited a little UA in our own way.  In fact, it’s pretty remarkable how intertwined the outdoorsy/technical/adventure culture has become in everyday life.

I remember the days when L.L. Bean was a genuine New England experience. Until the Original Preppy Handbook came along, no one outside 13 colonies had ever even heard of it.  REI was the domain of serious hikers like my brother Greg, who was president of the Dartmouth Outing Club back in the day and even had the honor of being written up in Yankee Magazine for having to be evacuated off the Presidential Range after tearing open his leg on a crampon.  It’s a long story.

Nonetheless, I’ve said too many times to count that classic, preppy styles often center around the idea of repurposing functional clothing for daily life.  Who do you think started the trend of wearing foul weather gear to the office anyway?

The difference is that too often men who yearn to be manly men turn themselves in to affected parodies of their heroes. Everyone role plays a little bit; I like messenger bags, but I’m no bike messenger. Others sport military fashions yet have never so much as looked at a gun, or wear team jerseys that barely fit over their couch potato paunch.

These fashions are usually a desire to connect with a cherished role model or organization. It’s a search for identity and belonging; aspirational but not too often overblown.

Yet when it comes to the couture mountain man look, moderation seems to go out the window. Even if you really are a transcontinental hiker, please don’t sport your Fortress Peak GTX hiking boots in the office. It’s tacky.

When worn in moderation, I think the outdoorsy look is classic, fresh and emotionally fulfilling. One feels a little more independent, perhaps a bit lone-wolf about life. Rustic.  There are some rules, however.

Avoid at all costs strapping on a back pack while wearing a business suit.  It looks silly and detracts from the professional seriousness of the suit.  At the same time it also diminishes the coolness of the back back.  It’s college kid stuff.

If you do want to use a technical or messenger style bag while dressed up, opt for dark solid colors and not too many straps, buckles and other dangling things.

Some looks, like the pairing of a technical jacket with selected business attire, can be really quite pleasing.

With casual office environments still common, the appearance of rip stop cargo pants and hybrid “trekking” sneakers have proliferated as well. Throw on a moisture wicking pullover to combat the air conditioning’s chill and you might as well be at base camp. I suppose it’s better than flip flops and shorts, but why not at least try and dress a little better for for your office mates?

Pairing cargo pants and and a casual oxford, pulled together with a wide leather belt, is a great alternative. Instead of a North Face Skareb 55 backpack, why not a Jack Spade waxwear bag instead?

A mountaineering coat may be rugged and functional, but its scale and overall feel should still match your other clothing. Neon orange and yellow serve a purpose in the wilderness but can be a little too much on an early morning metro ride. Try sticking to neutral, earthy colors instead.

Should the weather turn and force you to throw on a rain shell before heading out, the basic rules of proportion still hold true. The outer jacket should cover your suit or sport coat and not leave it hanging out the bottom.

If done well, the look says you are at home in both the outdoors and the corner office. Your clothes, particularly in this case, should not look gimmicky or forced.