If you are going to walk, the first and most important piece of equipment is going to be on your feet. It makes sense, its the only part of you that will come in contact with the ground (usually, but that’s another story)
Don’t go out and buy the first pair of boots that look pretty, stop and consider the kind of areas you are really going to go to.
Walking on tarmac is going to suggest a shoe, or trainer with a hard wearing sole, and cushioning under your foot. Grassy fields warrant a more aggressive sole pattern to stop you slipping, and if you fancy fell walking a boot is essential to protect your ankle from twisting over.
The boots I chose are “Alt-Berg” which sounds foreign, but they are made in Richmond, N.Yorks. If you visit Blackburns Outdoor in Huddersfield, they will make sure you get boots that fit. They are an independent retailer, but more importantly, they have been out there and done it, so go and see Steve and Carol. Do this! It is absolutely the best thing you can do.
Between your footwear and your skin you are going to have some extra cushioning in the form of 2-layer or single layer socks. For me this question was answered long ago, I choose Bridgedale Trekker socks. They work for me, personal preference I know, but its not a bad place to start. Again, these can be sourced at Blackburns, or you can get them from amazon.
Ok, moving swiftly up the leg, trousers. Lightweight, but quite hard wearing. Able to dry quickly. Most important comfortable, and a place to pop your map and compass wouldn’t be a bad idea. It sound like a tall order, but I have found that cragghoppers have just the thing. I surround the bottom of them with a pair of Rab gaiters and that me sorted. If its rainy, a pair of NorthFace waterproof pants quickly gets put on over the top. No need to remove boots, the half leg zip works really well, even in high wids these are easy to get on.
While we are on the subject of the lower half, boxers or briefs? whichever you choose, I would like to suggest you steer clear of pure cotton, it holds moisture, and if you get hot you will sweat. Moisture is what will cause rubbing, and it will hurt! You will have no problems finding technical fabrics made into boxers, but briefs is tough. You could do worse than Rohans briefs that wick moisture away. I can vouch for these in all seasons.