Oops, I guess cycling is a hobby. Should have read before posting this. Oh well. Might still help.
Here we have stores that sell "last seasons" clothes at a steep discount like TJ Maxx. Recently we were looking for workout clothes for my husband (his were literally falling apart). Instead of $40 at Sears, a new workout shirt in the quick-dry fabric was $9 at the "last seasons" store. Much better!
For the work clothes, you just need a few good items. Think "cost per wear" not upfront cost. It doesn't matter so much what a great-fitting pair of pants costs (within reason) if the same few pairs will be worn hundreds of times each.
I had a 70% plus another 50% off the remaining price coupon for the Banana Republic outlet last Christmas, and got 2 good pairs of wool dress pants and a suit.
Good quality, I paid 15% of original price and I won't need to buy either again for many years, I bet!
If you do bike to work, it may a bit counterintuitive on the initial price , but there's companies that make items exactly for cycling to work and still looking/functioning great.
What about buying less, but better?
Eg one dark gray and one navy pair of pants from a company like Outlier (that makes super durable, comfy, 4-way stretch, reinforced for biking , quick dry /stain resistant /won't wear thru stuff you can cycle to work in and still look great), then wear only those two pairs for a long time.
(There are similar companies, but Outlier is one I like)
http://shop.outlier.cc/retail/pants/