I can't dress myself!!!

April 15, 2008 5:25 PM

What to wear? I don't want to commit a fashion faux pas...

I am having dinner at Charlie Trotter's in Chicago this weekend. But I am a jeans and t-shirt kind of girl, with little experience 'dressing up'. I thought that I could wear this really nice black dress I have, but should I wear black tights/stockings, or a color? Are black shoes ok, or would I be violating the spring dress code? Or do I need to go out and start fresh? Any helpful thoughts on fine dining?

posted by bolognius maximus to clothing, beauty, & fashion (12 comments total)

What is the weather like in Chicago? How long is the dress? Black hose with black dress might be too heavy. It can look dated as well, depending on the dress.

The weather looks like it's going to be in the fifties this weekend. If it were me I'd buy something new. It wouldn't be a waste because you could go to this outfit for several occasions. You can never go wrong with nice pants, a fine gauge sweater (preferably cashmere or cashmere blend), a piece or two of nice jewelry (does not need to be real) good shoes with a bit of a heel and a nice bag.
posted by LoriFLA at 5:47 PM on April 15

Without pictures this question is almost impossible to answer. Here's my best go at it, though:
A black dress is fine as long as it isn't too long- you don't need to wear a gown!
You don't need stockings- save those for the dead of winter, if ever.
Black shoes are also fine if they are sufficiently feminine. Don't wear clunky black shoes. If your black shoes are heavy/clunky/too flat, do you have any silver, gold, or dark bronze heels? Preferably toward the more muted side of the metallic spectrum. If you do a colored jacket or wrap, try to make sure the shoes and the wrap coordinate; not the same color necessarily, but at least complimentary.
Make sure your jacket matches the tone of the dress! By tone I mean sufficiently dressed up: don't wear a fleece or an old boxy sweater. A nice trench in any color would do, or maybe a dressy cardigan or wrap in a contrasting color? Don't go out and buy something new (unless you want to!) but do pay attention to how your outerwear matches your main pieces.

And don't worry too much about being super-fancy, since many people under-dress for nice dinners out. You won't be the most casual person there, trust me.
posted by ohio at 5:47 PM on April 15

a black dress and a cute cardigan are great. wear plain black flats--you can get a pair of black ballet flats at target for like $15.

if your dinner companions are dressing up, black sheer hose is fine, as is no hose (or nude) but i think stockings in a fun color would also be perfectly acceptable as long as everything else is understated. (black dress, black flats, purple tights, black or dark gray cardigan)
posted by thinkingwoman at 5:53 PM on April 15

Wear your dress. No hose/tights/stockings. Black shoes or black strappy sandals. A nice dressy coat in a bright colour to make the whole ensemble a little more springy.

Unless, of course, you want to buy something new. I wish I had a list of recommendations but that's not really feasible not knowing what you look like or what your budget is like.
posted by snoogles at 6:00 PM on April 15

Sorry that I forgot pictures! I tried to find something close to the dress I have, and this is the closest thing I could find (pretty close, just not plus size). I think it is going to be in the 50s-60s on Saturday in Chicago. Would silver strappy Kenneth Cole shoes (very similar to this) be ok (without tights), or better go with a different shoe? Thanks for all the replies so far!
posted by bolognius maximus at 6:03 PM on April 15

The dress is lovely and the shoes are lovely and they will look great together - just make sure to get a good pedicure!
posted by Evangeline at 6:06 PM on April 15

Charlie Trotter's is pretty upscale, so I wouldn't recommend the colored tights. Black dress and black shoes with sheer or no stocking is best, and you can make the outfit less somber with sparkly jewelry or a different colored heel if you have one.
posted by rmless at 6:06 PM on April 15

Yes I agree, the shoes and dress go well together! No stockings with open toes, but you probably know that already.
Take a cardigan in case it's air conditioned in there...
posted by rmless at 6:07 PM on April 15

that dress is fine for Trotters. The times I have been there have been women dressed fancier--but not much. There will be women there is fancy every day clothes (as opposed to that dress, which is more of a cocktail or party dress). You might get cold with bare legs (it should be in the low 50s, but it's damp). If you're still in your 20s, sparkly stockings and a closed toe shoe would be great. If you're older, maybe not (says the woman on the far side of her 30s).
posted by crush-onastick at 6:14 PM on April 15

See, you can so dress yourself! I like the dress, too, and think it would be lovely with a pretty pendant around your neck, or skip that and do great earrings. A really fabulous bit of silver jewelry and a wrap (color would be great) are really all you need with that combo.
posted by ersatzkat at 6:17 PM on April 15

wow! Thanks so much for all of your answers! You guys have really helped me out! I will do my best to look and be fabulous. And I hope the elf food is delicious...
posted by bolognius maximus at 6:24 PM on April 15

Have fun, bolognius. I love the dress and shoes.
posted by LoriFLA at 6:27 PM on April 15