Hello,
My husband and I have traveled to many countries (8plus, some of them multiple times) and I can only speak for our travel wardrobe choices. We have only traveled in May and Sept/Oct.
I think it is smart to not draw attention to yourself, if you can help it. My husband was pickpocketed and he makes sure he keeps anything important in his front pocket or in hidden pocket in pants/shorts.
I am always concerned about my wardrobe and looking put together. I get a little obsessed to be honest. (If you are obsessed like me; then I can even tell you that I lay my "outfit" out with jewelry etc on my bed and take a picture so I know what to pack, and what can be worn different ways for multiple looks!!!.. this does help to not overpack) I'm sure I've lost a few readers by now!
My wardrobe: (I try to stick to a certain color scheme for our trip to make accessories/shoes etc. easier to select) I bring a pair of jeans, a pair of jean capri's, black capri/navy (depending on which color matches my color choices for that trip) ( have always worn capri's and totally acceptable). I bring a great black shawl from one of the travel stores, that I wear on the plane and tie around my purse if needed during the day. It's great for throwing over shoulders in churches/restaurants etc) I bring a jean jacket and a few scarves, a few cardigan sets, and several tops and a rain jacket that I can roll up. Most importantly are shoes.. I have had foot injuries and surgery, so I'm always on a mission for comfortable shoes. I bring a ballet flat from B.O.C., a merrill tennis shoe and a pair of merrill or mephisto walking sandal (which you can buy cheaper usually in Europe). A few cute sundresses and you are good to go. I've seen shorts on women, but i would pack a longer version, if you wear shorts. I also pack an Umbrella that I can collapse in my daytime bag. A crossbody bag is very important so you have better control for safety. (We've seen people have their backpacks snipped with scissors by the Louve in Paris)
My husbands wardrobe: (I don't lay his clothes out and take pictures!! ha!! I'm not that crazy!) A pair of jeans, a pair of black slacks ( I found on a travel site, that don't wrinkle) , a pair of black shorts and khaki shorts, short sleeved polo shirts, a long sleeved shirt or two and a lightweight all weather North Face jacket, a pair of merrill tennis shoes and a pair of black loafers.
On the coast there are tons of places that sell beautiful linen clothes if that is something you like.
We have really seen about everything over the years. The main things that make people stand out as tourists, are the name tags/badges, new white tennis shoes, people who wear their front (suppose to be worn under shirt) pouches with $ etc. on the outside of their shirts or so full they stick out, (so they obviously draw attention), tshirts and big travel vests stuffed to the max. .. Makes me chuckle thinking of some of the things we've seen that scream tourist!!
I think you have to be aware of your surroundings and have common sense when traveling. Of course it's hard to not draw attention when standing on a corner looking confused and at a map etc. which we have done many times.. ..but for the most part people are very kind and willing wherever you go to help you out and are not there to take advantage of you or any of your belongings.
Jody