Shoes, I can't answer for a woman. As a guy, I keep a pair of comfortable walking shoes for trips. Sometimes I'll throw in a second pair, depending on the trip.

As for a shoulder bag, I've had the same Le Sportsac for the past 25+ years. I can't seem to wear this out. It's a very dark blue.

It's been from the U.S. all over the world, 50+ times.

Good thing is, it has 5 zippered pockets, so it naturally keeps pickpockets at bay. I've used it mainly for passports, wallet, cameras, $$$ and the like.

However, it will hold 5 bottles of wine if necessary, or 10-15 cans of beer, depending on your needs/wants.

I swear by my Kipling bag - I have a cross-body style that is great. It is large enough to fit a guidebook, basics like small wallet, pen, chapstick, sunglasses, phone, and a small bottle of water. I used to have a larger bag - more messenger-style but I found it too big. I couldn't easily hold the larger bag on my lap and things like that - but the smaller size is much nicer for that. The strap is adjustable so I can wear it cross-body or over my shoulder. The fabric is very nice - resists stains and abrasions. I like that the bag zips up completely and also has a snap buckle - double safety from someone unzipping the bag and reaching in. And there are a couple different compartments/pockets to keep things organized.


Here is a link to the site - I don't see the bag that I have shown anymore, but there are quite a few that look good.

http://www.kipling-usa.com/home/index.jsp

This one is pretty close to what I have - mine is black though:

http://www.kipling-usa.com/product/index.jsp?productId=12179974&cp=2999461.2999759&parentPage=family&cid=1214907

Oh - I forgot to mention shoes I bought these from Sketchers last year and I really like them:

http://www.skechers.com/style/22025/sassies-stylized/blk

I usually wear a pair of mini-socks with them - I don't know what these socks are called, but they are made of the same type of material as tights - a little thicker than nylons - and they just cover the bottom and sides of the foot so they don't show with this shoe.

I most often wear sneakers (athletic shoes) because I have never found a walking shoe that is more comfortable for long days. Merrell loafers are a second choice. I just use a normal purse/pocketbook with a sturdy strap. I don't like "travel purses" because I don't care for lots of different pockets, zippers, etc.

I usually take athletic shoes too for long days of walking. I love my Asics - wear them for all sorts of fitness, long walks for fun, long walks for exercise - they really hold up well.

The other shoe trick is do NOT take anything brand new. Make sure you have had them and worn them around for awhile and know they'll be comfortable (made that mistake more than once with new-ish shoes/sandals).

I travel with over-the-ankle hiking boots from Vasque. After I fell in Switzerland my chiro convinced me I needed the support, if you don't want the support you still need sneakers or very well constructed walking shoes. Your feet will HURT otherwise - what do you use for walking in the UK? I also take Ecko sandals and switch off on fine days - used to be Birks, but they don't have enough grip.

BTW, are you sure you want to travel with jeans? Aside from being hot, they take up a lot of room and take a long time to dry.

I always travel with jeans - they only take up a little more space than cotton and I can always get more wearings out of them between washes to the time to dry and the extra space evens out.

I love Merrell's and Clarks. They have many different styles for casual or more dressy outfits. Zappo's has a good selection and you can return them for free if they don't work out.

I also really like my Baggelini bag. I bought mine for a great price at TJ Maxx but you can get them online or from other outlets as well.

http://www.ebags.com/category/handbags/cross-body-bags/b/baggallini?origin=left_nav

As Suze said, whatever shoes you end up, make sure they're broken in before your trip.

On a related note, I wear shoes for at least 10-15 minutes in the store before buying, walking around the store. If they're shoes that I intend to wear all day walking/hiking in, I wear them longer.

I've learned the lesson that they may feel good for a few minutes standing in the store, but pressure points etc. only reveal themselves with longer wearing and moving around in them.

As for bag, what do you normally need to carry in it? I usually take a couple in various sizez when travelling so that I can be flexible depending on the day's activities and weather. Do I need a jacket but want the ability to stuff it in the bag? I generally always carry a water bottle, but it may be the small 350ml one if I know I'll be able to refill it easily or the larger 750ml one if not.

This is my larger bag: http://www.mec.ca/AST/ShopMEC/Packs/ShoulderBags/PRD~5027-232/timbuk2-clipper-tote.jsp

I also use it as my personal carry on item.

This is an updated version of my smaller travel bag:
http://www.mec.ca/AST/ShopMEC/Packs/ShoulderBags/PRD~5026-303/mec-globetrotter-shoulder-bag.jsp

Most bag manufacturers have a bag similar to this.