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First off I suggest buying the best you can afford, and make sure its what you want. I have a lot of bike clothes I never wear, but I found it on sale so I bought it instead of what I really wanted. The clothes the I really like have lasted me a really long time.

For shorts I'm super impressed with the new Yeti clothing line, and the black color shorts are subdued enough that you won't feel like you are advertising for them, the hard part appears to be getting the right size, and since they are hard to find that may be a huge issue.

I am also a fan of the Troy Lee Designs shorts, I have heard great things about the Ruckus and the skyline, but I like having a very breathable pair of baggies so I would suggest the Ace, which are super expensive, but I think they will last you years, especially if you buy the black color (cause they won't show stains). Troy Lee Designs® | Bicycle Pants & Shorts

I recently bought these, in blue, and I really like how light they are, but they are so thin that I'll be suprised if they last more than one season: Evo-X Short | SUGOI Performance Apparel

My longest lasting baggy shorts are from Endura, they are kinda heavy weight, so they are best in spring and fall, but I've had them for 5 years and they still look new, I think these are newest iteration of what I have: Endura - Products

For spandex shorts I really like the Pearl Izumi Elite shorts, they have a somewhat thin pad, but once your as$ gets used to riding you will prefer thin pads cause they dry faster and don't wad up into a ball and try to cram into your b-hole. these: Shorts

For jackets I have two that I really love. The first is a lightweight softshell that I found used, and I think something like this is similar: Men's ELITE Softshell Jacket - Pearl Izumi

The second jacket I absolutely can't live without is the RAB Cirrus wind jacket, it is a super lightweight wind/light rain jacket. It packs down to the size of a tennis ball, and fits my tall-skinny body type reallly well: Rab Cirrus Wind Top - Men's | Backcountry.com
(patagonia makes one that fits a bigger dude called the houdini: Patagonia Men's Houdini® Jacket - Windbreaker)
 

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Thanks for suggesting the pearl izumi elite for shorts under my baggys i want a thin pad something not to big like I am wearing a diaper LOL.
 
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