Look on it as a challenge. Think about what you need (or at least think you need) and then consider how you can use your skills and talents to get it cheaper. Don't put yourself down, you do have abilities that can save money and give your ego a boost.
There are the short term, single use items. Don't spend much on these. You need some fancy clothes to wear on a cruise vacation or to a fancy do. These are once a year items. Now, if for some reason you have been nominated for a prestigious award--Best Actress, Nobel Peace Prize--by all means go all out. Splurge. The world is watching.
In other situations, the ones you are more likely to be involved in, don't spend more than absolutely necessary. This is where sewing skills could be useful. You can whip up a dazzling sequin covered top for less than $20 and the sequins will cover up any wobbly seams. No sewing skills?
See if you can borrow or try a consignment or thrift store. Use your treasure hunting techniques and skills. Glamorous apparel is inevitably in good condition from infrequent use. Some cruisers gain weight from cruise to cruise and have to upsize.
Sometimes you have to be patient and wait for a solution to present itself. I have been contemplating purchasing a small camping trailer for some time. As any dog owner can tell you, vacations can present problems when you have a pet(s). Airlines make it difficult and expensive to bring a dog on a flight, not to mention a few that have gone astray while in their care. Hotels and motels will sometimes label themselves as pet friendly and then use it as an excuse to add a $40 a day, per pet uncharge. I can understand that there will need to be a thorough cleaning including carpet shampooing at the end of the stay but an additional $560 for a week's stay with two small dogs is pushing it.
Wisely, I considered renting a camper for a trial run. Always a good idea with major purchases. For example, not that I was ever considering it, but driving in a relative's Mustang convertible a few times put me off that purchase permanently. Too difficult to get in and out of, too much wind your face and too much of a temptation for the driver to speed and subsequently get noticed by roadside patrols. But camper rentals specifically state, No Pets. I suppose they can't say No Children although small children can drop ice cream cones on the carpet and mess it up that way. Pulling even a small fibreglass camper requires a larger vehicle with a tow package so the entire project is still in the fantasy stage.
For now, a still living at home daughter provides pet care. We've yet to find a future solution but then they all seem to miss us so much when we're gone so we'll have to cope with the guilt factor first!
I remember that in The Tightwad Gazette, Amy Dacyczyn advised against getting premade pudding cups even if they were free (due to some extreme couponing venture). Your children (or you) will develop a taste for them and they won't always be free. Getting into that situation can lead to feelings of deprivation.