I think I've done everything suggested here, except having a tailor take something in (though my very handy fiance has helped make minor adjustments - lots of hemming of dress pants from second-hand stores, etc). I wear the same clothes until they literally fall off/down, buy second-hand or discount, sell or give clothes to family, etc. The most versatile thing in my closet would be a fav pair of skinny black pants - works with almost anything!
My problem is that now I have hit the end of my closet - there simply is no more

. I can (tightly) wedge into my smallest pair of adult jeans (or equivalent size that I was at age 14). I can comfortably wear all but one of my shirts - and even then it's a mental comfort thing (need to work on flabby underarms - ick

)
Almost EVERYTHING I own is wayyy too big - especially pants. I go to my favorite second-hand store every 2-3 months, but lately it's been slim-pickings for decent jeans or dress pants for work. I finally bought a new pair of jeans last night at a discount-retail store (TJMaxx) so I got a $60 pair of pants for $25 --- Apple Bottom jeans for girls with booty!
But I am severely strapped financially and I need clothes! I'm tired of walking around with the "dumpy-drawers" look of a toddler in bad need of a diaper change! I'm feeling good and my body is looking better than it has in years - I wanna enjoy, darn it!
Also, I am FREEZING now that fall is coming and I've lost all my insulation! Anyone else having the chills after weight-loss??