This post was a request from one of my housemates about how not to look like a tourist when you're traveling. I think it's funny that people get really stressed out about what to wear while sight-seeing in other countries. The hardest part for me is finding an outfit that works for a lots of different situations--say you're traveling around Italy. And you want to visit some cathedrals, go out to a nice lunch, do some shopping, and walk around a lot. You need something fancy enough for a nice restaurant, modest enough for a church, and comfortable enough for lots of walking and shopping. I have two go-to outfits for sightseeing: sundresses and tops+jeans, because they're both so versatile. I put together a jeans+top outfit here that would work for all of those situations, and still keep you looking cute.
J. Brand Bombshell Cigarette Jeans, $174 at shopbop.com, Frannie Camisole, $78 at anthropologie.com: As far as jeans go, I know at least in Europe wearing ratty, light jeans around will make you seem like more of a tourist. However, a clean pair of black jeans like this is great because you get the comfort of a jean (and these have a ton of stretch and a nice high waist), but you still get a very polished look. It's very Audrey Hepburn. And I love this white top. I am a huge fan of tops that are basic, but still have a fun and unique twist. This one is easy to style around, since it's white, and the sweetheart neckline and fitted waist are extremely flattering. It's a step up from a tee, but it's not too revealing (especially if paired with a little sweater or jacket).
Frye Melissa Button Boots, $328 at fryecompany.com, J. Crew Jenna Cardigan, $70 at jcrew.com: I'd do boots for sight-seeing. Flat sandals can lead to gross, dirty feet, and ballet flats always tear my feet to shreds. Please don't wear high heels around cobblestone streets. You will hate yourself. Flat boots are a great option because they have a formal feel, but they're comfortable and easy to walk in. The riding boots are very classic and polished, which works nicely with the vibe of the black jeans and the blouse, and they're a nice, rich leather, so they wear well and look very expensive. Then I'd add this navy blue cardigan on top. It adds a little warmth and coverage for, say, going in a church, plus it's cropped to a great length that highlights the waist and doesn't add any visual bulk. The navy adds a little color, but it's still a neutral, so you can wear it with a ton of other outfits.
Foley + Corinna Snake Chain Cross Body Bag, $425 at shopbop.com, Ray-Ban Oversized Wayfarers, $145 at shopbop.com: The only practical bag for sightseeing is a shoulder/cross-body bag. It keeps your hands free, but has lots of storage, and is hard to pickpocket from. I love this bag. It's leather, so it's sturdy, the black makes it versatile, and it has a bunch of little details that make it really fun. The chain on the strap and the zippers down the side add some edge, and the ruching adds an organic feel and some visual interest. It's a basic enough bag to wear with a ton of different outfits, but it still has some sass, and it's large enough to store a guidebook, camera, some snacks, your phone, etc, etc. I kind of want it for real life...As far as accessories go, lots of jewelry isn't so great for traveling. It can attract pickpockets (paranoid but totally true) and if you lose it in a foreign country, chances are you'll never find it. Sunglasses are a great way to accessorize an outfit as an alternative to jewelry. I like these over-sized Wayfarers because they're big enough to protect the skin around your eyes from the sun, and the classic style is flattering and goes with a lot of outfits.
Images via shopbop.com, jcrew.com, fryecompany.com.