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The Blog

Approachable inspiration for a stylish life. 


What to Wear to an Outdoor Office Retreat

Kristen Berry

Cutter Scout Reservation, Boulder Creek, California

Cutter Scout Reservation, Boulder Creek, California

If you know me, this will came as no surprise: I have never been camping. That is, until last week, when my company held its annual team retreat, this time during a two-night camping trip. As someone who likes to bring it wardrobe-wise at the workplace (and in every other way, really), this trip posed a bit of a packing challenge.

We were to depart for the campgrounds from the office Thursday morning. And while the itinerary for the trip was kept a surprise, I knew that previous retreats involved team brainstorms on business topics and presentations of the group’s ideas before the entire company. Given this, I wanted to kick things up a few notches above what I might wear on a casual camping trip with friends.

J. Crew V-Neck Band-Sleeve Top (   on sale for $36   ) and Garden Short (   on sale for $24   ), both in the print “Palm Frond.

J. Crew V-Neck Band-Sleeve Top (on sale for $36) and Garden Short (on sale for $24), both in the print “Palm Frond.

When I spotted this adorable two-piece set on super sale at J. Crew (an extra 40% off the sale price? Yes please!), I knew I found my perfect first-day-at-camp outfit. Normally I shy away from wearing matchy-matchy pieces at once. However, this set worn together gives off more of a romper vibe, which lends it a charmingly casual and playful vibe that feels appropriate for the setting. I also love that the elevated fabrics make the pieces comfortable and breathable as well as a bit more refined than actual campwear – the top is silk, and the shorts a surprisingly wrinkle-resistant linen. The other benefit of wearing a cute, work-friendly outfit to your trip? It works like a wearable conversation piece, just as I described in my recent post on the role fashion plays in my battling the downsides of being an introvert.

I should also note that this trip was largely more “glamping” than “camping” – check out the gorgeous accommodations put together by Shelter Co., which specializes in this sort of luxury outdoor event setup. This setting made my choice of outfit seem all the more appropriate.

If you find yourself invited to a similarly rustic company event, I recommend taking a similar approach of thinking through the types of items you would likely wear to the same setting sans coworkers (shorts, tank tops, jeans, t-shirts) and fancying them up just a bit by opting for work-appropriate silhouettes, attractive colors and patterns, and avoiding items that are too revealing or threadbare. J. Crew is my go-to resource for dressed-up casual pieces – I can always count on them for classic, preppy items with a stylish twist, and in cuts that I'd be totally comfortable with my boss catching me in.

These same rules apply for sleepwear, loungewear and workout wear, too. Don’t bring your teeny tiny hiking shorts or sexy yoga top for your activities, even if it’s scorching hot outdoors. You want these folks to respect you at your Monday morning status meetings.

Here are a few key wardrobe/beauty lessons I learned along the way to help you further rock your next camping/glamping trip:

  • Baby Wipes and Makeup Wipes Will Be Your Best Friend. Even though our tents were gorgeously appointed, we were still largely limited to port-a-potties in the bathroom department. Wipes were ultra-clutch when it came to quick clean-ups along the way.

  • So Will Water Bottles. Because brushing your teeth with fresh water right outside your tent sure beats having to hike seven minutes uphill in the dark to the one bathroom with actual plumbing.

  • Everything will Get Dirty. Like, filthy dirty. If you wear black, it will show every speck of dirt. Only wear comfortable, durable shoes you can basically throw in the wash (or can retire on the trip, as I did with the old metallic gladiators pictured above). Re-wear whatever you can to limit what will require laundering upon your return.

  • You Will be Colder at Night Than You Think. I regretted not having a hat, gloves and scarf with me around the campfire at night. Bring them even if you don’t think you’ll need them. I was extremely thankful that I had packed my fuzzy fleece PJs and thick, warm socks, though.

  • Get Your Beauty Sleep. Ear plugs kept me blissfully unaware of the sound of the port-a-potty doors slamming throughout the night. Next time, I’ll be sure to bring a sleeping mask as well, to keep the early morning sun at bay.

Special thanks to my awesome coworkers Erin for suggesting this post, and Allison for snapping the OOTD :)

Happy Camping!

- Kristen