Bottled water - you will find this surprisingly helpful, especially at night and for when you want to brew tea or coffee. If you sleep rough with a blanket over your head you will get thirsty.

Bedding: You need the best quality sleeping bag that you can beg or buy, the ones that say '1-season' or '2-season are actually perfectly adequate with a few added blankets. but if you can get a 3 or 4 season one and keep it then you are doing well, you will be ok. Cardboard or a groundsheet or ground blankets are essential as well, cold from the ground is as bad or worse than cold in the air and you do need something, as much as possible, between you and the ground at night, all year round.

Add as many blankets, small duvets and shawls to your bedding as you can get from the soup run or daycentre, the more beddng you have the more comfy you will be, the only thing is that you need to store them, if you are lucky then you will be able to find somewhere to store with permission. If you are clean and honest then some churches or households will allow you storage space as long as that doesn't disrupt them. If not then you have to look around for somewhere, put your bedding in black plastic bags to keep it dry, look for dense bushes on wasteland or at the edge of grass verges, woodland, under bridges, corners of derelict churchyards, etc etc, the one thing you need to do is hide the bedding from human view as best you can and hope no-one has a clearup and thinks it's rubbish.

Bed and breakfast: For rough sleepers who need a night out of the weather and stress sometimes and have an income from benefits, big issue or begging, don't declare yourself as a homeless person, turn up looking neat and tidy, book in at a cheap B&B for a night using a c/o address of a friend if possible, cheap B&Bs don't tend to ask many questions. A B&B will give you access to a shower or bath, hot drinks, a safe place to put your bag down for a while, and usually food as well. Make the most of what is on offer in the B&B included in the price, sometimes there are toiletries as well, check in early and check out as late as possible and the break from the elements and dangers will do you good.

Benefits: It is hard but not impossible to get benefits when you are on the streets, if you apply then you need an address, even if it is a c/o address usually, I have heard that if you really make an effort you can get benefits as a rough sleeper without an address, but I have to admit I don't know how it works and I wasn't able to do this. The benefits office like to pay benefits into an account for you, but if you have no account then they will issue a giro which you cash at a post office, you need ID to collect and cash the giro.
The type of benefits you are entitled to depends on your personal circumstances, but any money you can get helps towards hot drinks, food and other essentials. Being on benefits also gives you entitlement to concessions on courses and other things, and benefits letters can be proof of identity in some circumstances.

Begging: Often associated with drug and alcohol use, begging is a tough subject for me because there have been times when I have been unable to access homeless services and have been tempted to sit and beg, but I can't because I keep myself too well and I don't look like a rough sleeper.
Avoid begging unless you are in dire need, if you do beg, sit and beg, don't frighten and pressure people by going up to them, as this indicates classic desparate drug addict behaviour and people may report you.
If you beg, do it because you need food or other essentials, and say that you need food, people really do care and want to help someone in serious need, and they will buy you food and hot drinks and may ask if there is anything else that you need. But before you beg for food, exhaust all other options, saved food from soup kitchen, daycentre, bins, friends, vouchers, and that will help your pride and reputation.
The only time I have asked for anything is when I was starving and my blood sugar levels were dropping, and in that circumstance I usually ask for a hot sugary drink or water to make a drink, and when I explain my circumstances I am usually offered food as well.
It is classic that the only time I have been turned down for a hot sugary drink was by a certain church in London who would rather see a homeless person collapse than remember what the very foundation of the church is!
Ps I agree that not all beggars are druggies or alcoholics, but it should be possible to get money and food in other ways less harmful to yourself, and beggars are vulnerable and I know a number who have been kicked and beaten while begging. Also keep in mind that begging is illegal in some regions and towns, and the police are more than keen to enforce that.
Busking is slightly different, singing or playing an instrument in return for money is a trade of sorts and some people legally earn a living this way, buskers vary in quality, and if you have talent you may do ok, if not then you are making a fool of yourself.


Blankets: Essential, even if you have a sleeping bag, have blankets to sleep on and blankets on top of the sleeping bag, and a blanket to put round your head and shoulders at night - it feels vulnerable but makes all the difference.
Even if you are begging you need a blanket if you are sitting on the ground. Most soup kitchens, soup runs and daycentres have blankets available, some churches do.
An essential blanket for all homeless people, just in case, is an emergency reflective blanket, a little silver thing that opens out into a noisy bright lifesaving blanket that reflects your body heat back to you when you are wrapped in it, you can get them from some homeless services, most outdoor shops, and at one time the pound shop were selling them, two for a pound, carry one and you won't regret it, one day you may come back to your stash and find your bedding gone, or you may  find someone who has just ended up on the streets with no bedding, and the emergency blanket in your backpack will be a lifesaver then. Only use them in emergency, they are noisy and bright and prevent you hiding well, and if it is windy they are very prone to trying to blow away. I have used them and they do work in calm conditions, the bigger the emergency blanket the better, some are a bit flimsy, some are a good size, you can also now get ponchos or jackets made of the same material, also for emergencies.

Bins: A lifeline for a homeless person with few resources, but tough to access. Lets start with the big bins behind shops, some supermarket or bakery bins can provide you with a really good feast when you are hungry, but you have to be careful, you may be on CCTV, the bins are sometimes locked or locked in secure compounds, do not break locks but sometimes if you are neat and tidy you can bin raid where there is CCTV as long as the shop owners have not had homeless people abusing their bins and property, some wll turn a blind eye and grin about you sneakily accessing this wonderful source of food. But you may get chased off or have the law after you, the law will only tell you that that shop doesn't want you raiding their bins, unless you are always in trouble or have done any damage, in which case they will delight in being as unkind as possible. I have never been chased or warned off. I only raid the big bins that are unsecured, at night and when no-one is around. I used to raid bins overlooked by a police station :) Bin food can be bulky and hard to stash, it can be dairy products with sell by dates that day, fruit - too much for one person, snacks and savoury food, sandwiches and cakes, bulk bags of crisps or six packs of drinks, if you can't eat it all, dispose of the waste in bins or people may notice, or share it with other homeless people who you trust not to monopolise the bins and prevent you from getting your share of the goodies.

Smaller bins - household waste is unproductive, don't bother with that, then there are litterbins, litterbins have two uses, one is if you are really starving you can get the leftovers of people's takeaways from litterbins, but that is very risky, it is easy to pick up infections and worms that way, ionly do it if you have to do it to keep alive, I have done this. The final use, well known to my blog readers and reluctantly shared, is collecting McD's stickers, collect six and you can get a free hot drink at McD's, lots of homeless people do this.
After doing bins, it is a good idea to wash your hands, I know from experience that you can get ill and get infections from bins. I carry instant handwash gel with me and wash my hands after handling anything from the bins or off the ground, and yes, people drop half-eaten takeaways on the ground that you can salvage.

Boots: Essential, you can't be a rough sleeper, mobile homeless person and wear trainers or soft shoes, you will end up in agony with damaged feet and boots are also less perishable and tougher than shoes, hiking and walking boots are designed for long hard walks and are ideal. Don't get climbng boots though.
If you feel vulnerable where you sleep, sleep with your boots on, that will also keep your feet warm. Boots will support your feet and ankles during the inevitable walking, but make sure they are comfortable before you take to wearing them, don't be tempted to wear too big or small boots or the damage could be permenant. Get the best you can afford or the cheapest proper walking boots. Some really cheap ones aren't ventilated and that means you will have to take them off at night or whenever you can or your feet will suffer. Waterproof boots are best, if your boots aren't waterproof and you are out in wet weather for some time you can end up with athletes foot quite easily, as well as cold wet miserable feet. Wear thick socks with the boots, not thin ones that allow the boots to move around, that causes blisters and sores. Don't wear ribbed socks, wear several pairs of smooth socks or a pair of rougher boot or walking socks, or even sports socks.
Boots with quick release laces, proper laces, are best, easy to remove to tend your feet or give them a break from boots. Spray deodorant in your boots every so often to keep them fresh and dry the sweat.
Watch how the tread on the soles of your boots wears down, if it wears rapidly or severely one side but not the other then see a doctor or podiatrist about orthotics, orthotics, balancing insoles, may make a big difference to your walking, and you may find yourself walking easier with them.
Insoles, if you can get a cheap pair of insoles to cushion your feet, then do, most markets and pound shops have them.
Look after your feet, get the best boots possible, change them as soon as they are wearing down if you can. Don't wear work boots, they are heavy and not designed for homeless walking, the best place for decent boots at decent prices is outdoors shops, especially boots that are on special offer, never buy from a shoes shop.