Best cycling clothing sets for men according to redditors

Sure thing! I try to be as frugal as possible. Amazon has been good to my wallet.

Base Thermal Kit

Windproof Jacket

Overshoes

Balaclava Mask

Windproof Gloves

The thermal kit is very comfortable and perfect for riding in the 40s and 50s. Once it dips to the 20s and 30s, I add the jacket on top and switch from regular winter skully to the balaclava mask. My feet were noticeably warmer with the overshoes too. If you buy any items, order 1 size bigger. For example, I'm normally XL by American standard. These are Asian manufacturers, so I order XXL.

Happy [warmer] cycling!

There are a number of things you can do before you have to plunk down for a $200 leather saddle.

1. Before you buy special bike shorts, know that they sell gel pads that wrap around the saddle. This is not a good long term solution, but it's cheap and will help as you build up your muscles down there. Also, try some talc to let the boys slide around more smoothly.
   
   
2. Buy a pair of shorts liners before you blow a lot of money on "real" bike clothing. The liners are meant to be worn under regular shorts. The difference between the liners and the gel pad is that the pad in the shorts won't slide around as you move. This will help prevent chafing to your boys and your butt crack. The difference between the liners and "real" bike kit is that they're relatively cheap and you wear them under your regular clothes which can be a win if you don't feel comfortable appearing in public in spandex.
   
   Once you've used #1 to get over your budget hump, and you've tried #2 to find out exactly what bike shorts can do for you, then you can worry about whether or not you really need to buy the full kit.

I second the Sponeed Bibs, I have a set and love them. I went for their cheap jersey and bib combo set:

https://www.amazon.com/Shorts-Sponeed-Cycling-Jersey-Black-red/dp/B00VLM3ASU/ref=sr_1_15?s=sporting-goods&ie=UTF8&qid=1499355534&sr=1-15&keywords=sponeed

What are some good brands for buying jerseys and shorts? What to look for/look out for?

edit: ended up getting this.

I've been happy with the Zerobike stuff on Amazon. You can get shorts + jersey for ~$30.

They have some fun designs, and some fairly conservative designs. The green is a relatively good compromise between being visible, without being too wild.

https://www.amazon.com/dp/B01ELCTUX0/ref=cm_sw_r_cp_dp_T2_ddPDzbGVTYQ64

Cut on the short sleeve stuff is reasonably good; not super aero, but not frumpy. The long sleeves catch a bit more wind. Pocket design is good; the pockets are stitched to full depth, and they can take water bottles, large phones, or whatever junk you happen to carry there.

I like the look of that knox jacket liner.

https://www.amazon.co.uk/Lixada-Cycling-Resistant-Breathable-Sportswear/dp/B01M9DZO7V/ref=sr_1_6?ie=UTF8&qid=1481811709

I use one similar to one of these things, it's close fitting, windproof, has a high neck and as a double bonus I already owned it. Not well insulated though. It's a lot warmer than a fleece mind you.