Dressing like her Old Self

I would be embarrassed if the "office fashionista" commented about my wardrobe to me or others.

Think about it this way, if she put on a lot of weight but still wore the same clothes would you say anything to her?

She's not your friend, just someone you see in passing at work.You probably dont even think about her at any point of your day, except when you see her in person so why should you offer any advice to her about her clothing.

I think it would be a mistake. She may have a loose belly that she is very self conscious of and tighter clothing accentuates it. It takes time for everything to fall into place. If she is already self conscious about something and you make her self conscious about her current comfort level, you could accidently ruin her whole outlook. Sometimes its better to just provide compliments and let people be happy with their current situation. The only reason I posted this, is because that is my situation. I look frumpy in my big clothes, but I feel like I look dumpy in the clothes that fit. I know I am more than half way to my goal and that will change as I get closer to my goal, so for now I wear my big clothes. When my floating tummy catches up with my new abs, I will be happy to slip into something smaller. I think its touching that you are enthusiastic with her success but if she is as shy and self conscious as I am, you may do more harm than good.

after I lost all my weight I knew i needed to get new clothes, but i was used to baggy crappy clothes that weren't appealing. A coworker told me i needed to get new clothes, and honestly, i appreciated it and took it as positive criticism. Of course, i'm a dude and don't take things personally. I think you should tactfully bring up the topic and get her on track. You might make a really good friend if you approach her right. Something like, "I'm amazed by your weight-loss. The next step is getting you some hot clothes to compliment that beautiful body. How bout we go out for a shopping spree and get you some new stuff?"

bump

2 memories stand out for me from the last time I lost a significant amount of weight - I went from super fat to chubby (and I'm here to help me get from chubby to fit!):

1) Security guard at my office on a casual Friday - I was wearing my one pair of jeans, with the bottoms turned up, thinking that I was rocking the 'boyfriend' loose fit - his comment "Damn girl, your *kitten* don't fill them jeans no more!". No kidding - I spent most of the day pulling them up.
2) A friend of mine told me every time I wore a skirt that it was too big and not doing me any favours. One day she turned around and said "no kidding, it looks like you're wearing a bucket. Throw it away. Give it away. Get rid of it. I never want to see it again."
When I got home I used it to do some dusting to make sure I didn't just put it in the wardrobe and wear it again a week later.

It's hard sometimes to see the changes in yourself. I'm used to dressing to make sure my arms are covered, that nothing is too tight, that trousers are unlikely and jeans are out of the question (unless, like above, they were at least 2 sizes too big). Sometimes you can see the changes, but can't afford the wardrobe. And sometimes, when you know you're not done yet, you want to hold out until you hit your goal.

There's nothing wrong with telling her how healthy she's looking, and, seeing as you know it's intentional, worked-at weight loss, striking up a conversation about how she's managing it. The clothes subject could be worked into it - say you're looking forward to treating yourself to some new things in 5, 10, 15 pounds time.