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I’m going to a close friend’s gender reveal party this afternoon. It’s at a community yacht club in a New England coastal town. Dress code is “wear whatever you want.”
I lost more than half my body weight and my new wardrobe is somewhat small, so I’ve put together all the outfits that I think are appropriate, and hopefully flattering.
I’m looking for advice on what to wear today, and also general feedback on the outfits as I try to identify what works for me.




  1. LOFT skirt and off-white tee


  2. Quince linen dress - I feel like an oversized bowl of oatmeal in this dress, and I think I’m going to sell it because it’s too big. It’s an XS — come on Quince, really?


  3. Quince linen shirt dress


  4. Market & Spruce olive green dress and off white tee (I could change the tee to white or light pink). I’d love to wear it without a shirt, but the arm holes are cut too deep and it shows too much bra, plus my upper arms don’t look great after the weight loss.


  5. Vineyard Vines corduroy skirt and white tee. I’m wearing it with two different Jack Rogers sandals. The white is leather and more comfortable, but I think the navy crocheted one looks better.


  6. Lilly Pulitzer lobster skirt and white tee. I’m thinking this is more casual than I’d like for this particular event, and it needs a red tee. Thoughts?


  7. Jeffrey & Dana vintage maxi dress and black tee. I keep this dress because I was wearing it the night I met my husband, 28 years ago yesterday 🩷, but it’s too big (the back is laced up as much as possible, and I’m afraid it’s too much — see photo). Tee shirt because again, exposed bra and saggy arm skin.




Thanks in advance!


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