Fancy Moments on Adventure Trips: What I Bring to Be Ready for Anything
While most of the time when on the road, we’re in spandex of some variety or cutoff shorts and tshirts, occasionally, there are times when we need to be a little bit dressier mid-adventure. Maybe there’s a work meeting that comes up, or a nice dinner we want to go out to, or there’s an occasion we knew was going to be happening, like a wedding halfway through a trip. Whatever the scenario, it helps to be prepared—but not over-prepared. I used to travel with WAY too much nicer stuff and then end up not going anywhere where I needed nice stuff… or going out somewhere where moderately nice stuff would have been ideal but I was either waaaaaay underdressed or way overdressed!
This last trip was a month-long one that involved driving across the country twice, camping for 18 days in a tiny tent or the van, staying with friends, and finally staying in a crammed-full beach house with the Hurford clan. The trip involved MTB Nats, an Ironman, a hiking/MTB trip, a few beach days and a lot of work from coffee shops. But it also involved about five dinners out to reasonably nice places with friends and family, plus a date night. And this is just one trip! I’ve done a few with similar schedules in different temperature/climate variations, and I’ve learned a ton about what makes me happy & comfortable.
So… a few of my best pieces of packing advice for being prepared for any occasion.
The Little Black Dress (or some iteration thereof)
I freaking love this black tshirt dress. It’s hella comfy, it doesn’t wrinkle, it’s thick material so it isn’t see-through, it can be washed and dried in a normal machine, and it can be dressed up or down. (I think short sleeve is the perfect option here—especially with the shorter length!) I grabbed it at Garage a couple years ago and it’s been the best sub $30 piece of clothing I’ve bought in a LONG time. In the winter, I swap this out for leggings and a nice sweater plus a short long-sleeve dress that I’ll wear over the leggings, or dark jeans and a nice sweater, but the idea is the same. Wrinkle- and hassle-free.
For the Gents
Peter has two dress-up variations he brings everywhere. In warmer climates, he does these Rapha trousers with a button-down, and in the winter, he adds a sweater for over the button down. And since he wears the trousers as regular pants, not just for dressing up, he barely takes up any extra space. Mission accomplished. (Dudes have it SO EASY.)
The Right Jewelry
I’m a known over-packer, and that includes jewelry. But in the last year, I’ve gotten way more minimal there. I rarely wear anything other than my wedding ring on a daily basis, and I’ve gotten super into the “one signature piece” concept over the last two years. It started with a rose gold Nixon menswear-style watch that became my favorite accessory (and was the first time I’d ever spend more than $25 on a regular non-sports watch or bracelet of any kind). Then, Rhys May Jewelry made me a lily necklace to match my wedding flowers, and that came everywhere. And most recently, I started stalking Favor jewelry when they popped up on my Instagram feed.
Apparently, I have a thing for active women making rad jewelry. Rhys is a cyclist and now on the JAM Fund team and living in my old stomping ground of Easthampton, but I was in love with her funky style long before I knew that. And Favor’s founder, Monika Reed, is an avid hiker and super into travel!
This trip, a couple pieces from Favor came on the road with me: the Nomad bobby pin (appropriate!) and the Slip Hoop earrings. They’re handmade in Portland, Oregon, and as soon as I checked out the website after admiring the Instagram for a while, I forwarded it to Peter saying “please only buy me presents from here.” (He tries with jewelry but I am picky as F.)
Dress Up Your Hair
Moral of the story, I was not a big believer in bobby pins until I got this one. But as someone who spends 95% of her time with her hair up (ahem, see my undercut post here), I was stoked that I could look (and feel) a bit fancier by adding a hair clip to my damp, tossed-up hair. (The tattoos help a little too, but I don’t necessarily recommend that…)
I have a pair of everyday sandals that I’m wearing in this picture (from Madewell), but I’ve also worn this with sneakers for a more casual day wandering around, and I have a pair of wedge sandals for something dressier, i.e a last-minute nice dinner or wedding. (With our friends, anything is possible.) In the winter, I swap that for sneaker option and a high boot option, but usually skip the heels altogether.
Golden Rule: Keep. It. Simple.
Overarching point: When you’re in a van and trying to look nice, you’re not going to be able to do a full face of makeup. Silk shirts will wrinkle. Cashmere can get a little smelly when it needs to be washed but you haven’t been able to get anything hand-washed in a while / you don’t want your van to smell like a wet sheep as it dries. You probably won’t want to walk in those fancy heels from the car to dinner to the boardwalk. And hair straighteners need electricity to function. So, when you’re packing your ‘nice outfit,’ think about :
- Picking one garment that can be dressed up or down, versus multiple pieces (if you know you’ll have a couple of events, a jacket or shawl can help change things up, but really, when living the #NomadLife, expect to wear the same thing over and over.)
- Jewelry should be pieces that can’t get tangled, so something like a big watch, cool earrings, etc. that can uplevel an outfit but won’t end up getting destroyed in your bag
- Dress/leggings or jeans & nice top should be ones that don’t require any special care, i.e an iron or steamer and can be machine-washed (but will be OK if you can’t wash it before second wear!)
- Shoes should be super, super walk-able. (I have yet to wear this dress on an occasion that didn’t involve a fair amount of time spent walking)
- A way to put hair up (to disguise the unwashed nature) while still looking like you tried at least a tiny bit
- Makeup that won’t make you look like a panda the next day, i.e copper-y eyeshadow and clear mascara versus black eyeliner and mascara. Tents aren’t conducive to taking off makeup.
Let me know in the comments: have you been caught out on a trip where you were missing a reasonable going-out outfit?
Earrings and bobby pin gifted by Favor but all opinions are my own (and this is just the start of what I’ll end up buying from them!)
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