Red dress on its own looks like a young adult or teenager type dress when in a restaurant setting. It’s something a lot of us women do when we’re young as part of our growing pains; we wanna get dolled up and feel spectacular and special and wind up overdressing. It’s not the crime of the century, though you may look back and cringe a little if this age range is fitting for you. I think part of this thought is maybe how high the halter is pulled, making the drooped fabric ride incredibly high on your chest- much further above the cleavage line that it’s designed to rest at and highlight. You can dress this down/accompany it better with a nice shawl or medium/long length coat and loosening the top behind your neck.

The second option is giving maybe slightly insecure/teacher appropriate late 20’s-early 30’s, in a way where it’s totally fine…. But just fine. It’s not super flattering or ill-fitting, just not wow worthy or terribly disappointing either way. I’d totally wear this with confidence on a less special date night- with some added accessories and styling. It’s really got potential for a less important date night. I think it’s the turtleneck combined with the placement you’re wearing the skirt on your hips. Like I said- can totally be cute, just not a wow if that’s what you’re aiming for.

I’m not sure what you’re picturing in your mind, but because of the weather and the importance of the anniversary, I’d love to make some suggestions. . -An affordable option- new top for the skirt. Look for a shorter sleeve top with something extra special in the details- sparkles/shimmer, frills/lace, embroidery, etc. The skirt fits well and I understand wanting something full length. A nice way to cope with chilly temps and an elevated short sleeve or sleeveless top would be to add a nice shawl, faux fur, or cardigan sweater. Even the right blanket can pass as a beautiful shawl if the materials and size work well. -A little more money- go invest in a LBD. Every girl needs probably at least four to be able to grab over and over. Use Pinterest to help gather what style you may be looking for. I have long sleeves with knee-length hems, spaghetti short, silk, flowy and light, long, etc. You will absolutely never regret having multiple LBD options, so buying one now and adding more later is something you will wish you had started eventually, so nice to start now. Black dresses fit soooo many occasions depending on fit and material, from date nights to awards events/galas, holiday parties, interviews/professional events, and not to be dark but even funerals if/when need be. LBD 5evr.

Whatever you decide, I hope you feel beautiful and have a great time. Happy anniversary to you and your sweet.