Many will have only experienced warm summer weather riding and will know what to wear in those conditions. The usual combination for this type of riding is Bib Shorts – padded (worth spending some money on as we all know what happens when this area becomes uncomfortable – again check out the brand you are considering on a bike forum). Short sleeved top – ACC do a yellow one! – with 3 pockets at the back – more of this later. And shoes – again more later.
In the winter, life is more complicated and dressing more time consuming. Long cycling trousers are essential – usually called Bib tights – for riding between October and April/May. These are padded and should be tightish fitting around the legs and ankles. Thicker socks are also advisable but not too thick to fit in cycling shoes! Believe it or not feet get cold when cycling in the winter despite the fact they are moving all the time. An essential item of clothing is therefore a pair of over shoes usually made of waterproof (Gore tex) material. They may have a zip and will have a hole at the bottom through which your cleats can get access to your pedals.
Cycling shoes are many and various and can be expensive. The key change from what you may be wearing at the moment will be that the sole needs to be rigid to protect the foot and to create the most efficient transfer of power from you to the pedals and cranks. They will feel strange at first but you will soon get use to them.
Cleats need to be clicked in and out. “In” is not difficult to grasp. However you should expect to fall off your bike – usually when standing still – if you forget you have cleats and forget to twist to release. Everybody does it so do not be embarrassed unless it is the fourth time!!!
In the winter, most of the cold gets in through the front torso so you will need more than a short sleeve jersey when venturing out. A bit like walking, building up layers gives the best, least bulky, protection. A base layer of merino wool or some synthetic “wicking” material is necessary, followed by a normal jersey or preferably a long sleeved version. Then a top jacket in some sort of robust, goretex style, material. This may or may not have pockets but needs to be reasonably tight fitting to prevent unnecessary wind resistance.
Lastly, under the helmet, I would advice some form of tight fitting cap or a Buff, to keep out the chill. You can get ones with ear muffs but that is a fashion/style decision!
Putting on all this clobber takes time – it is worth taking it.