Your choice of footwear is as personal, and definitely as important as any other decision you will make about packing. Listen up, and choose wisely! Some people spend their entire trip in rubber thongs, while others wear heavy hiking boots everywhere. I have seen travelers who think it is cool to walk around barefoot in cities. Everyone has their own needs and preferences, and I will not try to tell you what kind of shoes to wear. But I will give you all the pros and cons I can think of.
Most of us are used to walking around in shoes. You already know how much support you need from your shoes. If you cannot walk far in flat shoes, you will have a difficult time adjusting to wearing rubber sandals all the time. If you can get by happily with sandals, you will save a lot of room and weight. But your feet are your most important piece of equipment, and you must make them happy -- and take good care of them -- or you will not be happy at all. Bring whatever shoes you will need to walk comfortably for long distances. Just don't take too many of them. If you take hiking boots and running shoes and sandals and thongs, they will take up far too much room in your pack.
I will recommend that you take at least one pair of real (closed) shoes with a certain amount of support for your soles, if not arches. People have gone trekking and bushwhacking in sandals, but shoes are much better and safer for your feet in these conditions. If you wear nothing but sandals, your feet will be more vulnerable to the sharp rocks, thorns, nails, broken glass, jagged and hot metal, toe-stubbers, and dropped boxes that inhabit the Third World; not to mention mosquitoes, bees, (snakes?), dirt, and a reasonable variety of parasites, as well. If you and your feet are tough, you will happily survive.
Plan ahead, and choose wisely! Don't take footwear that you have not already broken in and find comfortable to wear on long walks. Good shoes are your best friends, bad ones are your worst enemy. You can easily walk 5 miles (8 km.) just going shopping in a city; will your sandals or flat shoes carry you that far? Try them and see! A few long sightseeing days may involve three or four times that distance. Your legs may get tired, but your feet should not hurt if you have the right gear for them. I repeat, do not take footwear that you have not already worn comfortably; bad shoes are your worst enemy!
All of the footgear I mention below can be recommended and is used by many travelers. But no one shoe is perfect for anyone, let alone everyone, in all situations. Choose the ones that will be the most comfortable for you in most situations; you can't take an entire wardrobe of shoes! Along the way you will easily be able to buy rubber or cheap leather sandals and cheap running shoes. In modern cities you will be able to buy reasonably good running shoes. Good hiking boots will be difficult to find. You will be able to buy ordinary shoe laces in many places, but it doesn't hurt to take an extra pair, especially if you need long boot laces.
Sandals
If your feet are not used to the sun, you can get a terrific sunburn on the tops of your feet from wearing sandals all day. Slip in some socks to give them a break.
Rubber thongs (flip-flops, go-aheads, click-clacks) -- Many rural people in the Third World have adopted rubber sandals as their normal footwear. You can get a cheap, thin pair anywhere. If you want more substantial and comfortable thongs for general use, bring them from home. They are great for the beach and the shower, and some travelers live in them. They tend to get slippery when wet, and obviously provide little support or protection for your feet.
If you aren't used to thongs, you will initially get blisters under your heels and between your toes. If you try to keep them from making their natural click-clack sound, you will get cramps in your toes, so just let them flop around and make noise. They are the most common object of flotsam washed up along the coast and, with a little sewing ingenuity and some nylon cord, you can put together an unmatched pair or two on most any beach.
Serious sandals -- If you have some comfortable and sturdy sandals at home that you are used to walking in for several miles, bring them along. Birkenstocks are very comfortable shoes, even though they look like sandals. If you buy leather sandals on your trip, they will likely be uncomfortable and cause blisters for awhile; soak new ones in water, and apply a little oil to soften up the leather. The leather straps on sandals will eventually break or pull loose from the soles and be difficult to repair. If you are lucky, they will last several months.
Water sandals -- Rafting and kayaking enthusiasts use soft plastic sandals with heel straps for boating. Good ones can be reasonably comfortable and will last for quite a while. They are also great for the shower, for rainy days, and can be used to protect your feet when swimming, diving, or beach walking. You won't find them overseas, and you may have to go to a specialty sports shop or catalog to find them at home.
Light shoes
By this I mean soft, flat shoes with closed toes, but not much support for your arches. Canvas boat shoes, Chinese kung-fu slippers, and many other types of shoes fall into this category. They can be made of cotton, canvas, or even nylon, with a flat rubber sole. Light shoes for women may have more of a heel or arch support. They are cheap, light, easy to pack, and easily purchased overseas if you look around a bit. Their advantage over sandals is that they cover your entire foot and do not have straps or thongs to dig into your skin. If you have weak arches, you can even insert an arch support and walk around in them for hours.
If you take hiking boots, this kind of shoe makes a good second pair to wear around town or camp. If you plan to live on sandals alone, you might consider picking up a light pair of shoes like this for when you need more protection for your feet, or when your good sandals from home fall apart. They can also be more presentable than sandals at border crossings and other official encounters.
Sports shoes
Running shoes, runners, tennis shoes, plimsoles; there are now a million varieties. They can be very expensive and give excellent support for your feet, but not your ankles. Or they can just be ordinary shoes with little support or comfort at all. If this will be your main walking shoe, make sure you get a pair that is comfortable for long walks, and provides enough support for your particular feet. They are compact enough to be packed away when you want to wear sandals. If you have reasonably strong ankles, you can go trekking with sturdy running shoes. They will stand up to numerous stream crossings and dry reasonably quickly, but any leather on them will eventually rot from too much soaking.
You can buy some serious hiking shoes that look like runners but have a shank in the sole to keep your foot from bending around sharp rocks. On a long rocky hike, this protects your arches, and gives you better footing.
If you will definitely be taking hiking boots, running shoes will just take up extra room in your pack. Consider getting a very light pair of running shoes, or some sandals or "light shoes" that take up less room. You can always buy some cheap "second shoes" on the Road.
Walking Shoes
This is just a catch-all name for anything from a sturdy running shoe to a low-cut hiking boot. They can be flimsier than running shoes, or have a solid "shank" just like a hiking boot. Whatever you call them, there is a huge variety of footwear that may have some of the attributes of both. Check them out for price, support, and comfort if you are looking for good quality shoes to do a lot of walking in. Make sure they have some kind of textured soles for outdoor use, not smooth ones fit only for concrete.
Boots
Hiking boots give you lots of support, for your arches and for your ankles. If you are trekking with a pack, it is easy to turn an ankle on unsure footing. If you are used to living in the city, the entire Third World will be unsure footing, even getting into your hotel room! Hiking boots should have a solid "shank" that prevents the middle of the sole from bending at all over sharp rocks, saving a great deal of wear and tear on your feet. Try bending any shoe in half to see how well it will protect your feet in this respect. Modern shanks are made of synthetics and are much lighter than the old steel shanks.
The main drawbacks of hiking boots are size, weight, and being hot to wear. If you are used to wearing hiking boots, and don't ever carry them in your pack, these problems will not bother you. But you will end up wearing your boots every time you travel because they won't fit in your rucksack. If you don't plan to do much trekking, or if your ankles are reasonably strong, you will get by with some good quality running shoes or 'walking' shoes.
You can now buy very light-weight hiking boots that provide most of the advantages of the old six-pound mountaineering boots. They are softer, require almost no breaking-in, can almost fold up for packing, and are therefore not suitable for expeditions where you carry a 70-pound pack across loose rocks. Since you won't be on too many of such expeditions on your travels, don't bring those old clunkers. Light-weight boots are usually made with nylon and "split" ("splits" or "half-grain") leather, which is half the weight and toughness of "whole-grain" (or "full-grain") leather. Split leather almost always has a rough ("suede") surface which is more difficult to waterproof and gets dirty easier. Whole-grain leather may be either smooth or rough outside.
Another advantage of hiking boots is that they can be waterproof. Wet feet are no fun for you or your feet on a long hike. Unfortunately, complete protection from wet feet is almost impossible. "Completely" waterproof boots are made from whole-grain leather, have very few seams, and are sealed (regularly) with waterproof boot wax. These boots are heavier and more expensive than others, and you will have to carry a small supply of boot wax on longer trips. Eventually, they can still soak through, especially when you have to walk through a stream in them! Then you will also have to worry about drying and caring for the leather.
Boots made from split leather or nylon cannot be effectively waterproofed, but they are lighter and cheaper. Gore-Tex-lined boots appear to solve this problem, but they can be just as hot and sweaty as leather boots, and can still soak through eventually, despite the claims. Light boots made of nylon and split leather with a Gore-Tex liner are not as perfect as they sound, but worth considering; what you get is a light boot that is fairly waterproof but lacks the ruggedness and support of heavy leather, for about the price of heavier boots. Some full-grain leather boots also have a Gore-Tex liner, but your feet will still get wet from sweat.
If you are considering hiking boots, a major step in your decision may be accepting the fact that you will have to put up with wet feet at one time or another. If you can live with this, you may just as well go with lighter boots or running shoes that don't pretend to be waterproof. If you want to keep your feet dry, you can do it most of the time with serious boots and some extra care.
Socks
If you wear boots you will want to wear socks; if you wear sandals, you won't. You can wear running shoes with or without socks, but socks protect your feet from blisters and dirt, and keep your shoes from getting sweaty, dirty, and very smelly. Wear socks with new sandals that cause blisters. The main drawback is that socks are hotter than no socks. So try it both ways and choose the one that is best for you. You can get very short socks, or just roll yours down, so that your ankles still stay cool, tanned, and grimy.
You can buy socks anywhere, but the common ones tend to be very thin, made of synthetics, and wear out quickly. Very thin socks, however, can be just what you need for light duty around town to keep your feet clean and blister-free. You will be able to find reasonable cotton socks in better shops. Like underwear, white socks will soon turn some other color, so start off with another color of your own choosing. For long hikes, "body powder" (or baby powder) in your socks and shoes will reduce friction and help prevent blisters.
Trousers -- Take at least two pairs of trousers, unless you also take a skirt or two. More than two pair gets pretty bulky and you can always buy something local along the way. Get one pair that will stand up to hard, dirty travel and rock climbing, and another that is tough but looks more presentable in cities and public offices. Those who start a trip with stylishly frayed jeans are clearly short-timers. For the long haul, you'll want to start with newly broken-in trousers, and you will mend them religiously.
Cotton is always a good choice and pure synthetics are not nearly as good. Heavy denim jeans are a favorite and are certainly tough, but they are heavy, a real chore to wash and take forever to dry. They are also pretty hot to wear in the tropics. Loose fitting trousers with plenty of room in the seat and thighs may not be stylish this year, but they are much more comfortable in the long run. Avoid green. You can buy some variety of jeans almost everywhere, but not in large sizes. Can you trade jeans? Well, perhaps in the Former Soviet Union, but unless you know the score, they are hardly worth hauling around for that purpose.
Many people are taken with the idea of trousers with legs that zip off to make shorts. It sounds quite useful, but I am always leery of extra zippers that can jam and break. If you carry a lot of things in your front pockets, you may need to sew up the bottom from time to time. You can often find very light and flimsy trousers in local shops or beach areas; they are cool, and cheap enough to buy, even if they only last a month.
Belt -- You will probably need a belt to keep your trousers or skirt up, especially after losing a little weight. Take something simple and light. Leather is acceptable, but canvas and nylon will not rot or mildew like leather, although those little "boy-scout" buckles on many canvas belts soon break. I now make my own (travel) belts from black webbed nylon pack-strap material (3/4" or 1/2" wide), with a plastic rucksack fastener clip for a "buckler" -- you can buy these "spare parts" most anywhere you can buy backpacks, and sew them together to your size. Suspenders (braces) are a cooler alternative, especially if you are used to wearing them. Belts overseas are usually plastic or leather and of mediocre quality.
Shorts -- Some travelers live in shorts in the tropics. On some trips where I knew they were not acceptable, I didn't even take any, substituting nylon swim trunks in beach towns. We are used to seeing bare legs, but in many places they are considered indecent and therefore insulting to the local people. In Latin America, only young children and homosexuals wear shorts, except in beach areas. In Muslim countries, male travelers may get by wearing shorts sometimes, but only because the people are too polite to complain. Women in shorts will only be acceptable in 'modernized' countries or beach areas; in any case, showing bare legs just encourages hassles from men.
In many areas though, you can spend months in shorts, so find a pair as sturdy as your travel trousers, with legs that are not very short. Loose fitting ones with big pockets are the most comfortable. Since they are not commonly worn outside of former British colonies, good shorts can be hard to find on the Road. In New Zealand, businessmen are seen going to work in suit-coat, tie, and matching dress shorts. Good on 'em!
Remember that trouser legs provide more than modesty. They protect your legs from relentless sun, thorns, scrapes, insect bites, poison plants and hot metal bus parts. Shorts are not always the best for bushwhacking, even in hot climates. They are great in the tropical rain, however, and dry more quickly than trousers. Wear them when you can, but be aware of local sensibilities.
Skirt -- Many female travelers don't bother taking a skirt because they never wear one at home. Light-weight cotton skirts are cool, comfortable, compact, easier to wash than trousers, and easily purchased wherever you go. They aren't always good for rugged traveling, but quite comfortable around town. In some conservative areas, trousers are considered inappropriate on women; you can usually get by, but bring one skirt along for Muslim countries, at least. Skirts should fall far below the knees to be acceptable in many places.
Shirts, blouses -- I could easily take a dozen shirts for different situations, but you can't take everything. I recommend taking two or three short-sleeved shirts or blouses and one or two long-sleeved for everyday wear. Don't take this many if you also bring several T-shirts for everyday wear. Make sure they are comfortable, washable, and look good even when dirty.
In most situations you will be wearing some shirt that covers your shoulders. For warm weather you can usually wear T-shirts, but I personally prefer a collared short-sleeve shirt made of a cotton-polyester mixture. I carry two or three of these and wear them constantly; I get them with one or two pockets and a square tail that can be worn outside for coolness. They are very light and cool, weigh almost nothing, "never need ironing", rinse out and dry easily, and the collar can be pulled up to protect your neck from sunburn. For some reason, they seem to last forever; I have had two that survived as old friends over several trips. You can open some front buttons for more coolness, depending on the social situation and your gender. They go right into the shower with me and dry out while I walk around in them.
If you like sport shirts with a few (placket) buttons at the top, these are a good alternative if they are not too heavy. If you ever sweat, take note of how the moisture shows up under your arms; on some shirts it is hardly noticeable, on others it quickly becomes an obvious dark circle. Take the former. Don't take anything that needs pressing to look presentable. You can buy reasonable short-sleeved cotton and cotton-poly shirts in most cities.
Women's blouses should follow similar guidelines, although there are infinitely more styles. White blouses look nice but quickly show dirt; limit yourself to one white one. Light is great, but see-through fabrics may be provocative in some cultures. Remember that delicate fabrics, fancy buttons or lace may be easily damaged (when being pounded on rocks), so you'll have to wash them out yourself.
Long-Sleeve Shirt -- One light-weight long-sleeve shirt is recommended for both men and women. Even in warm weather, you will be thankful for one to protect your arms from sun and mosquitoes, and there will be a few countries where bare arms are considered quite immodest for both men and women. You can always roll the sleeves up when you want to. You can easily find a light cotton-polyester collared shirt which will also be very presentable at any official offices or border crossings. In India and Pakistan men and women can buy a "camise" of the local style which is reasonably cool and fits right in; you can even have one made for you in a day or two.
A heavier long-sleeve shirt can be useful, especially in cooler climates or for serious bushwhacking. Depending on your tastes and destinations, you may choose a heavier long-sleeve shirt instead of the light one mentioned above, or as part of you cool weather gear. Cotton flannel or heavy weight cotton are good for warmth and durability. They are better protection not only from cold, but also from mosquitoes (who can bite through thin fabrics) and very hot sun, and will stand up to rugged situations. My latest is a heavy rip-stop cotton which I find much more rugged than flannel.
T-shirts -- Some people live in T-shirts and it may be a major part of your wardrobe. Get them loose enough to let a little air circulate; a form-fitting T-shirt can get very hot. Personally, I find them too hot and constricting, especially around my neck; but I take one for diving and as an undershirt in cool weather. Avoid white. For better or worse, T-shirts are good trade goods and you can see locals wearing the most astounding specimens from all over the world.
Swimwear (swimmers, swim togs, bathing suit) -- Take at least one swim suit, and two if you will spend much time on the beach. Light nylon swimmers weigh very little and don't take up much space. Men will usually get by with swim briefs, but a pair of nylon swim trunks (shorts) will be more appropriate in some places, and can double as shorts, at least in beach areas; so get some with pockets if you use them. A passable alternative is a pair of gym shorts. Women should take a one-piece suit which is less than risqué for general use. Bikinis are not well accepted in many places but you may be able to wear a bikini (or less) at some beach 'resorts'. Some women just roll their one-piece suit down to the waist when they find themselves at a liberated tourist-only beach. Men and women will be able to buy quite ordinary swimwear in large cities, but bikinis will be very hard to find in the Third World; try the Club Med.
Sarong (lungi, kain, pasin, kanga, pareu, lavalava, lap-lap) -- The basic garment of Asia and the Pacific, this is a length of thin cotton cloth about one meter by two or two and a half meters. Besides being useful as a beach garment and bathrobe for both men and women, a sarong can be used as a top sheet, beach blanket, towel, shawl, scarf, carry bag, window curtain, picnic blanket, and changing room -- to mention just a few. Because of its many uses, I recommend getting one that is not already sewn together into a sheath, as they are typically worn by many Asian women. If you want to use it for a sheet, get one that is long enough to cover you from head to foot, to keep the mosquitoes off; Indonesian "sarungs" tend to be cut a bit longer. Sarongs wash out easily, dry fast, and take up little space. If I'm headed for the beach, I carry two. When not in use as a shawl, or when you're walking on the beach, just gather it into a sash around your waist.
Wear a sarong to the shower since you don't have to drop it to the wet floor to put it on; it is equally convenient when using the toilet. You can buy them almost anywhere in tropical Asia and the Pacific, as well as in East Africa. The cheapest ones are printed on only one side; get one that is dyed through, and soak it in cold salt water (the ocean) to set the dyes. If you need to start out with one, just buy two yards (meters) of cotton fabric, the thinner the better. You can have hems sewn in the ends to prevent fraying if you like. You might find a pricy Hawaiian 'pareo', but a stroll through a yard-goods shop should turn up some reasonably interesting-looking material for much less.
There are dozens of ways for men and women to wear sarongs. First, find a style you can use without losing your sarong while you have both hands full! Then experiment with the local methods, see how other travelers wear theirs, and ask them to show you. You can pick up numerous techniques, including how men tie theirs into shorts when working; I prefer the Balinese look, myself.
Bandanna -- Let me say here that sarongs and bandannas are the epitome of travel utility and improvisation. Like its big cousin the sarong, the number of uses you can find for a good-sized cotton bandanna is limited only by your imagination. It can often serve as a head-band, dust mask, neck or head scarf, sun or sleep mask, four-cornered hat, hot pad, wet compress, tablecloth, and seating mat. You can also use it as a washcloth, bandage, tourniquet, or fly swatter. In a pinch it serves as a towel, pot scrubber, carry sack, tooth cleaner, or short cord. I have seen slender women wearing them as a top garment. And of course it is the catch-all handkerchief and rag. Its classic western style is imminently American, but imminently useful; take several and give some away, they are not generally available.
Cotton underwear is the best; synthetics are just too hot and sticky, and may encourage fungus growth. White underwear and T-shirts soon turn various funny colors and are the sign of new or novice travelers. You might as well start out with beige or other colors. You will be able to buy quite ordinary cotton underwear (even in colors) just about anywhere, so don't take any more than you need.
Underpants (pants, knickers, panties) -- Take three to five pairs of whatever style you wear normally, with the emphasis on comfort over stylishness. Anything that binds or rides up will plague you on long bus rides. Wash them out often, and buy new ones as they wear out. Paper underpants are a good trick for short trips, but you won't find any more on the Road. A few men go with no underpants at all; it is cooler, but not very practical when you've got intermittent diarrhea. In addition, dirty jeans can easily lead to urinary infections this way.
Undershirts -- Aside from the ubiquitous T-shirt, mentioned above, are sleeveless singlets (tank-tops, vests, muscle shirts) and string shirts. These are best worn under other clothing in cooler climates for a little warmth, without the constriction of a T-shirt. You can also use 'tank- tops' for the classic traveler's beachwear, and many women prefer singlets to T-shirts as underwear. String T-shirts may be good under a shirt for situations where you sweat a lot, like trekking.
Bra -- Bring two or three of the bras you normally wear most comfortably, but lightweight cotton is the coolest. Like other underwear, beige or off-white will look better longer. They can get quite sweaty, so rinse them out often and scrub the straps and elastic to prevent sores. If you don't normally wear a bra, you (women) should take one along anyway, because there will be situations where you should have one. Some locally worn blouses are very thin and cool (in India, for example) and quite acceptable as long as you have a bra on underneath. You can buy common bras everywhere, but the more bulky styles predominate.
Pantyhose -- These are good for keeping a chill off and are beastly hot in the tropics. They won't stand up to much hard traveling, so keep them for special occasions or substitute dance tights or long underwear for warmth.