That being said, there are many ways to re-wear a dress to make it look different and new. You would be amazed. Having such a large family, the "dressy" events never seem to end. My sisters and I take great pride in our skill of re-wearing dresses. Here are some of our tricks:
Before you buy: Before you buy any dress you need to assess how many times you can potentially wear this dress. If it costs $300, but you can wear it 5 times.. in my book that dress is $60. You are better off buying a great $300 dress vs. a one-time wear $150 dress.
Cardigans: A cardigan changes the entire look from the waist up. If you are re-wearing your dress to a "dressy" event, find a fancier cardigan. There are so many out there, embellished, lacy, gem toned, floral, colorful, etc.
Shoes, Purse, Jewelery, etc: Your shoes and purse should usually go together (not match per se, but "go"). If you have a simple black dress, you can try a colorful shoe and a colorful purse. Try hoops instead of pearls, silver instead of gold... a charm bracelet instead of bangles. Or maybe even a belt.
Hair: Your hair really changes your look and the entire vibe of your entire outfit. Re-wear your dress with a low pony tail, a flower clip, a headband, or other hair accessories. I am a big fan of the flower clips. I have them in many colors. You can also clip them on your dress to make them look like part of it.
Alterations: If you are really tired of wearing your dress, take it to the tailor and get it altered. I do this a lot, it really cracks up my tailor. Usually I bring it in and try and on and ask him what he can do with it. Take the sleeves off, shorten it, taken it in, whatever. Usually it costs me about $12 - $24 and it looks brand new. Think Project Runway.
Change / Add Buttons: Find some fancy buttons online, colorful, cameo antique looking, pearl, etc. The fanciest of buttons are usually less than $12 for a dozen. If your dress has buttons swap them out. OR if you have a plain black dress, get some fancy buttons bring them to your tailor with the dress and tell him to sew them around the neckline. Congrats, you will have made your dress look $100 more expensive with a few buttons.
Some parting words: Don't be ashamed to wear the same dress over and over again. My sisters and I think of it as a sport. You win by wearing the dress the most times, and the least distinguishable from the original.
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