Confessions from a serial overpacker: I’m the kind of girl who packs 10 outfits for a 3 day trip because #options. I would’ve loved to have gone shopping in Nashville this last weekend, but given that there was -10% space in my carry-on, I allocated that time to filling the empty hole that is my stomach versus my suitcase.
That being said, one of you asked me for both options and the ability to close your suitcase without having to arm wrestle it shut. Specifically, versatile outfits for those trips where you’re Tarzan during the day but Jane by night. So, here are all the outfit options using only two pairs of shoes and two bags to take you from the trails to dinner.


Cargo pants never left us. The highly-rated Rectrek Pant from Outdoor Voices is made of elements-resistant fabric, but tailored enough to dress up with a pair of heels and a sleeveless jacket for dinner. I chose the Osprey Ultralight Stuff Pack for your daytime activities because it’s packable for when you want it stow it away, but roomy enough for all your essentials when you need some extra space.
My go-to affordable, yet stylish bag with a surprisingly amount of space is this one pictured above from Amazon. The pochette style can be customized to fit however much you want to carry, and it comes in all of the neutral colors to go with any outit.
Note: My all-time fave pair of sneakers are the New Balance Fresh Foam Cruzv1 Reissue because they’re lightweight, supportive, pull-on, and well…fresh looking. If you’re doing more serious hiking, you’ll want a more heavy duty boot.


Tanks with built-in bras and bodysuits are your best friends on trips. They can be dressed up or down and, when rolled tightly, can be reduced to nearly nothing in your suitcase.
For a versatile evening shoe option, pack your favorite pair of dressy sandals with a chunky heel. A larger heel gives you more support than a stiletto in case you need to do a bit more than just walk to dinner and back home.


Matching sets are basically a foolproof way to look stylish without trying. Pictured above is one of my fave recent Amazon finds for workout gear. Wear just the crop top with a pair of dark jeans for a more polished evening look and pair it with a denim jacket or shacket for chillier evenings. Layers are key when you’re traveling! Coming from the East Coast where the weather can swing 20º in one day, you don’t want to be caught drowning in your own sweat at 3pm and shivering at 10pm.
And lastly, a neutral shift dress that looks great with just about anything. While I wouldn’t necessarily suggest hiking in this, it’ll be easy to sport with a pair of sneakers if you plan on doing lots of non-backcountry walking and exploring. This one from Lululemon is made specifically for the active woman, and the midi-length ensures that you won’t need to hem it even if you’re petite like me.

Looking for more day to night outfit inspo? Head to my Instagram to see four ways I styled this “base” outfit made up of a bodysuit and denim shorts.
I hope this was helpful in freeing up juuuust a bit more space in your precious carry-on!
Till next time,
Anna
“Let go: how would your life be different if you learned to let go of the things that have already let go of you? From relationships long gone, to old grudges, to regrets, to all the ‘could’ve’ and ‘should’ve’ to the dead friendships you still hang onto…free yourself from the burden of a past you cannot change.”
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