Every winter, it seems Alex and I are out of town just about every other weekend for a quick trip. Hello Weekending! The locations are usually the same, on a rotation: Boca, Chicago, LA, Tucson, and NYC. We do occasionally travel to other cities, but no other places have our hearts quite as much as these five.
And since we take these weekend trips so often, I’ve become a pro at packing a carry-on and know exactly what I’m going to need, and when it’s one pair of shoes too many.
THE TYPICAL WEEKEND CARRY-ON BAG
ON THE PLANE
Over the years, my signature airplane outfit looks like this: leggings, a chambray shirt, and tan ankle booties. The boots are so easy to slip in and out of while going through security. Also, since these shoes are the clunkiest, I find that it’s best to wear them on the plane, as to save as much space in the carry-on as possible.
DINNER + DRINKS
A dark, moody floral print top paired with the same leggings, and same ankle boots. Paired with a slim black cross body purse, you really can’t go wrong. It’s super easy to freshen up in under 5 minutes once you land at your destination, and right back out the door for a meal and a beer!
SIGHTSEEING
Lightly distressed denim, my staple gray sweater, sunnies, and a pair of white chucks. A day chalk full of museums, gardens, sightseeing, and downtown walking equates to comfy laced closed toe shoes. The large tote bag is a must for long days. 
DATE NIGHT
I usually always try to pack at least one dress. Nothing too dressy, but something a tad more feminine that just pants. Even if I never end up wearing it, I’m glad it’s with me as a backup. The black crossbody purse and flats go well with dress, so it’s a no brainer to throw it in the bag. 
BRUNCH
Leggings, a tight white sweater, printed flats, and messy curls is the only combination I want with my eggs and mimosas. I like to pair this with my cheetah print flats, and my tote bag.
Usually there’s one or two more activities jammed in throughout the weekend, and any of these mix and match outfits will do. That’s the beauty of a capsule wardrobe, guys! Do you get it now?
OK, so that is what my typical weekend carry-on bag looks like these days. We’re off to Tucson next weekend for another quick trip, and another year of the G&M Show! What do you usually bring on a weekend trip?