I do not need to tell you not to wear stilettos. There are two sorts of opinions people have about stilettos: the type that knows stilettos are irrational and doesn't care because of how fabulous they make their legs look, and those who would rather go barefoot, and neither one finds my advice relevant.
One of my biggest struggles traveling used to be how many pairs of shoes to bring. Practical shoes for travel? Shower shoes? Hiking boots? Running shoes? Fancy work shoes? Goin' out shoes? Water-socks? The possibilities are endless, and I have found (more than once) that my suitcase was so full of shoes that there wasn't space for anything else. Like clothes.
I now have a strict travel code: Thou shalt not bring more than three pairs of shoes, and thou shalt always bring two pairs of shoes. Why? Unless you are headed to a yoga retreat or towards a beach vacation (which I'll get back to in a bit), you will likely be walking a lot more than you normally do. This is certainly true on air-travel dates, when there is much standing, walking, waiting in line, waiting on the moving walkway, etc. Having an alternate pair of shoes helps in any long day, so long as neither pair is a pair of pointy heels.
Fancy shoes: Try to find something comfortable. This may not be possible for the black tie event or school reunion, but if you're headed to a wedding, graduation, or other event where people will care less about your footwear, be kind to yourself. I love Aerosoles, Danskos, and J-41.
Beach shoes: Bring shoes that cost $1-$3. Plastic flip-flops are the best... anything that can be sandy and will not get hot on the beach (no black bottoms). I like brightly colored flip flops, but also have some that look remarkably like cork-like while still being completely water resistant.
Running shoes: If you intend to actually run (as in, you have a regular running routine and know that you will not only have time but will make the time to run) you will need actual running shoes. The socks pack right inside, as do the shorts and top (probably). Bring one or two pairs of running socks only, and wash them in the sink of your hotel. The same is true for winter boots, should winter boots be your travel shoes of choice.
Walking shoes: There are dozens (ok, hundreds) of excellent walking shoes with nice sole that are significantly smaller and lighter than actual running shoes. I recommend these for those who enjoy walking, using an elliptical trainer, or a stationary bike.
Tiny slippers: These are essentially socks with non-slip bottoms and a tiny bit of cushioning. This is not the time for bunny slippers, but you might really appreciate them if you are staying in a place with a cold floor, or if you are staying with in-laws and you want them to think how put together you are by bringing your own slippers.
1. Pack your smallest shoes and plan to travel wearing your largest shoes, such as your running shoes or work "heels." If your travel shoes are sandals, I also recommend keeping the teeniest pair of socks in your purse for the nippy airplane temperatures.
2. Stuff things into your packed shoes, if possible (think socks, undergarments, pjs).
3. Select packable shoes, like flip flops or "crushable" walking shoes.
4. If sparkly, fancy, or otherwise highly polished footwear is required, pack each shoe inside an old tube sock to prevent rubbing or contact with clasps and zippers.
5. Make sure you bring clothes that match all of your shoes, not shoes that match all of your clothes.
