So my starter for 10 - this is for winter/colder training:
Base layers: I have allsorts, from expensive to cheap, and as i'm essentially fine with anything Merino
Mid-layer: Typically a cycling top year round - but anything technical to wick moisture away from the base layer
Top layer: I have several, it depends on the exact conditions as to what I wear,
I haven't used mine a lot yet, but early indications are that the Pactrac jackets are very good for a wide range of conditions.
DHB Windslam Roubaix - well fitted, comfortable and warm. Very versatile, a base layer, this and my ultra-packable pretty much takes care of everything from November-Feb/March.
Altura transformer jacket - no insulation, but windproof and the removable arms are a boon for when it is a chilly start but warms up during the ride
Pearl Izumi Barrier WxB - I have never, ever been wet from rain when using this. To be honest, I rarely wear it as I tend to overheat in it, but when it is needed it is great. It also will stuff into a jersey pocket, so is great for longer rides with changeable conditions. No insulation though, so will need layers underneath.
But my no.1 piece of kit is my Endura ultra-packable jacket (others will do). This has been used across 4 seasons as a layer, and is awesome if the rain comes down when your out. Stuffs into it's own pocket and fits in a jersey or jacket pocket with little bulk, so really easy and lightweight.
Shorts: Always bibs for me unless on the turbo, i have 2 pairs, Altura Airstrem, which fit great and are good for rides up to about 3 hrs, and my Assos shorts - simply the best, supremely comfortable, perfect fit. I could wear them all day, and they last forever. You will cry when you first spend the money, but after 5 years with mine, i have still no intention of changing, and i think they actually represent better value for money long term than cheaper options. This will be very gender specific though, so would be good for the ladies to weigh in on shorts for the girls.
Others: I tend to layer, so this makes up the rest of my kit -
Leg warmers - Endura thermal knee warmers & Funkier full length. Both are great
Arm warmers - Endura Merino ( great, but short!) and Endura thermal. Endura are slightly better for me.
Gloves - I believe that is is ok to be wet as long as your warm, so I don't go in for waterproof gloves. I have Castelli neoprene gloves and have not been cold yet - if it's biting wind, I wear a pair of running gloves underneath. I also have some engineers gloves which are great, but i'm blessed with not normally getting cold hands.
Head wear - In the winter I wear a skull cap (I have a Specialized and an Adidas, both are great), and if it's really cold a merino buff as well for my neck/face.
Overshoes - I have a pair of neoprene toe cover which are OK for Spring/Autumn, but for really cold weather I use Endura neoprene overshoes and these are great. I have recently got some Velotoze overshoes, which so far have been great, but I have yet to test them on a cold ride.
Finally, a great site to pick up some bargains from is Sports Pursuit. It is a flash sale site, with some great discounts available, but as always, shop around to ensure you are getting the best deal. www.sportpursuit.com/sales