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Your main concern will be to avoid blisters – you don’t want these wretched things at all – so, the best way to avoid them is to make sure your boots are just about perfect, however, you can do things to increase your chances of avoiding them. When you get your boots, the insole that comes with them isn’t of a particularly great quality so, rip this out and replace it with an after market Sorbathane (or the like) insole. These are a lot thicker, more comfortable and offer superior shock absorbsion for the feet. Your choice of socks will also make a big difference. I settled for a pair of the 1000 miles socks – so called because they are guaranteed blister free for 1000 miles. They are, basically, a sock within a sock. Blisters are caused by the friction of a sock rubbing on the skin, what happens with the 1000 mile socks is the sock rubs on the inner sock and not your skin. They worked perfectly for me. However, some of my fellow HM’ers wore two pairs of walking socks without problems. You wont know until you try.
Other clothing should be warm and comfortable. Waterproofs should always be carried, including leggings. The shower type overcoats will keep a shower at bay but they do sweat badly if worn for long periods which means you’ll get wet with sweat anyway so, it’ll be worth investing in a proper breathable waterproof coat for the really wet days. These can be expensive so shop around – I found mine on e-bay for £20.
Trousers should be loose fitting to prevent chaffing at the tops of the legs. Jeans should be avoided at all costs. Good, light, walking trousers are ideal but very often a kilt is worn and these are very comfortable and surprisingly warm – just be careful what you wear underneath, if you go commando then you may have to apply the cream to the tops of the thighs etc.
The main problem on a long walk is sweat – it comes from everywhere and can really make you quite uncomfortable. There are ways of reducing this by wearing what is known as a Base Layer. This is a specialist garment that wicks away sweat from your body keeping your other clothing dry. These can be expensive to buy, so, if you can afford them, go for it, if not take a few t-shirts with you and change them en route if possible. It worked for me.