I've tried to think ahead on my riding apparel needs and get gear that works in as many conditions as possible. I also watch out for closeouts on good quality gear. Yesterday's outdated gear was just a few weeks ago at full price and the latest and greatest. Once the new improved model comes out...it is no longer the latest and greatest and the price drops substantially.
I've been using an Olympia AST2 jacket for several years now. Last spring, I sold it and bought the Olympia Ranger jacket...the replacement for the AST2. There's not much difference in the jackets at all. There's a lot to like about both jackets, but perhaps the two features I like the most is it is waterproof and has flow through venting. A lot of jackets are waterproof, but the vents open up into the waterproof layer. With these Olympia jackets, they designed the vents to open up all the way to your body directly, yet retain the waterproofing. That makes these jackets true 3-season riding jackets.
A year ago, I picked up an Olympia Dakar jacket. The old, out of date, no longer latest and greatest version...for about half the price. I was going on some trips where the 4th season...hot summer...was going to make this worthwhile. Between the two jackets and the liners that came with them, I can ride in anything from 100+F down into the teens. And if it rains, I'm dry. I can't remember when I wore my rain gear last.
For pants, I picked up some Olympia riding pants. I haven't used my old mesh pants in two years since I bought these. I bought something that was two versions back of the current Olympia XMoto2 pants that now retail for $350. For about $200 less. The thigh area has a large panel of textile material that unzips and tucks nicely into the lower leg. You never feel it down there. Depending on your bike and the airflow, you'll get some nice cooling off the open mesh area on the top of your thigh. I didn't understand initially about the way the wind/waterproof liner worked. I do now. It's simple, effective. Olympia includes a separate liner (and I think a quilted insulated liner too, though I've never used it.) If you use riding pants with a built-in waterproof liner, you'll find that your boot soles will catch on the liner. After awhile, the seams get pulled and water leaks through. With this design, that hasn't happened in about 4 years of heavy daily use. And if it ever does start leaking...any rain pant from your local sports or hiking store will work just fine. Lastly, in the summer, the liner isn't making you sweat.
Gloves...I look for the sales at the season's end. Now is a good time to buy summer gloves. The stores want to dump their summer glove stock so they don't have to store them over the winter.
I have heated gloves for the winter. I think if I had to do it again, I'd buy glove liners instead. Why? Because that way I can get the heat I want, and get the glove that suits the conditions best for that particular ride.
Boots...I used to wear utility boots that I got at Big 5 Sporting Goods. They worked, but I find I prefer "motorcycle" boots now. The TourMaster Epic boots are a really good boot that'll give you a nice bang for the buck return. I bought the non-Air version first. They get a little hot in wearing them. I bought the old version "air" boot next. Both are comfortable enough to ride to a hiking trail and then hike in for a few miles.
Lastly, if you're really ATGATT, think about an airbag vest. The Hit-Air is about the same as the Helite version, just less expensive. It works. I dropped my bike once and landed against a curb. As I'm lying there, I'm realizing that I don't hurt. I should. That curb edge that I hit hard should've broken a couple ribs...but didn't. Oh!...it was the airbag vest. I won't ride without it.
Chris