Here’s my two (or more) cents (and I only made it through about 1/3 of the comments above so I apologize if it’s repetitive and nagging… and long!)
1. This is pretty controlling for someone whom you aren’t married to. If you are officially engaged and discussing JOINT budgeting, then that’s different. But him approving every top you buy is a little reaching. He may just be in a panicking mode because HE isn’t used to spending (as you mentioned) and doesn’t know your budget.
2. That being said, discuss with him that you aren’t comfortable with this. Don’t pull the “not fair, I do what I want” response. It won’t go over well and will come across too harshly. Express that it’s hurting your feelings and making you feel controlled. He probably doesn’t realize that this is how it came off. BEFORE you sit down and talk, print out something showing YOUR current expenses. Show all the proof you just posted about (having more money, etc). Show your expenses, how much you spend on “fun” things, and how your future finances may look. If you are seriously considering marrying this guy, you shouldn’t have a problem talking about this. Have this stuff ready, and then after you express your distain for his restrictions, show him the facts. Show him how you’re managing money smartly.
3. The suggestion of an “allowance” is brilliant and works perfectly… for a marriage situation. Again, being that you’re not married it doesn’t make sense to do that right NOW. BUT…. mention that maybe you’d be willing to do such a thing once you are married.
4. My husband and I came to a resolution when it came to my clothes shopping. Every time I buy something, I get rid of something else. If you turn your hangers backward, and then turn them front again once wearing/using that item, This will be easy to track what you don’t wear in a year’s time. Again, mention this to him as a way to compromise with your shopping. Also… you’ll find it refreshing to have a constantly changing wardrobe and not have things lost in “i’ll wear it later” section of your closet.
5. Most importantly… remember that this is the man you are thinking of marrying. Speak calmly, maturely, and kindly. He will respect that you came to him about it instead of stewing or going behind his back. The dress for a surprise trip? I would just simply tell him something like “honey, I bought a dress for this event but I really want to keep it a surprise for you to see. I would love to see your face for the first time about it because I like it so much”. Make it seem like this hiding of the dress is really more for his sake – which it should be!
side note… I read your comment about returning 90% of stuff you buy online. If that’s the case, why purchase at all? Stop shopping online! Go TO the stores, try things on, and chances are the amount of money you spend on clothes won’t seem so shocking. Even if you DO return the things you buy online, it’s still a matter of having the initial funds to purchase. In the time between buying and returning, you’re left with that amount out of your bank account – and into his head for your shopping “habit.
Again.. just some input! I wish you the best on this.