Well, I personally would not but at 50+ you start realizing that it takes more than just working out to lose weight - it means giving up things that you love - like bread and wine.

Go for it! I LOVE the dress! I have a crush for denin dresses

If you have a plan and the motivation and time to implement it, go for it. Oooh, that tank dress is gorgeous too.

I have no idea whether you should keep it, but I do love the dress.

What makes it a bit tricky is the slim cut of it...even with stretch it might feel uncomfortable until it's loose-tailored on you vs. just-fitting. But. It's a great dress!

Years ago I had a top that was sooooo similar. I loved that top so much.

Oh, man I like that Rachel Comey dress, too!

OMG. The railroad dress is perfect for you! Wow, I just love it so much.

Right, but back to the first dress...

My other issue when I used to do this, was that my passions may have shifted or changed by the time the item fit and I wasn't excited to wear it, even though I could. But that doesn't necessarily happen to other people. I can easily fall in love with a new piece of clothing a month or two later, and then I am faced with the guilt of having purchased an item that doesn't even fit quite right. It makes for a bad situation for me overall. But if you maintain love for an item you own for a long time, that that won't be an issue.

Okay, I don't "know" you but considering your recent history, I think it's a reasonable gamble. You said it's been a difficult year and you've lost and kept weight off recently-- in the last 5 years. Only you know your own behavior and if you are changing it to make a difference but I'd bet on you based on what you've said. However, I would probably want to have some other ideas about how to "use" the dress (as a coat over something, not buttoned?) just in case because the price is a little high. I do love that dress tho--tres cute! I'm pretty obsessed myself these days with denim and chambray dresses.

Agreeing with Scarlet, but I confess, and I may be alone in the universe with this opinion, I don't really like the dress. I don't think denim dresses are appealing in general and I feel like I've been seeing this one for years.
Also I feel like all the collar and seaming action might compete with your face.

I try not to make these kinds of purchases -- or my bigger problem: purchases because they are great deals -- but what works for me isn't necessarily right for you. You've certainly proven to have great willpower (with both your past weight loss and your long shopping hiatus) so I wouldn't bet against you if you decided to give this dress a go. FWIW, I really love it.

PS So interested that you have purged all of your floral. I would love for you to write a post about what else you have purged and why. Is this trend-driven, or motivated by personal taste and new direction?

I would say go for it - and it sounds like you did! I'm glad, that's a really cute and versatile dress. You strike me as a very disciplined person, so your 10-pound goal sounds achievable.

I take those gambles, if I know I'm close to fitting the item - and I know I can use the item long-term (i.e., over a couple of years, through periods where I might gain and re-lose a few pounds).

I've gotten better at judging what is a good gamble - but again, I approach it as a long-term project, knowing that if there is a holiday splurge and I gain some weight back, it will take some time to lose it again.