Avery,
A guy I’m seeing invited me to a bar this weekend to celebrate his birthday with his family and friends. I want to look good for a night out, but I also don’t want his family to think I’m a tramp. What should I wear?

This night will be a very delicate operation: you must walk the fine line between hot ‘n’ classy and hot ‘n’ trashy. Just because there will be real adults there doesn’t mean you have to totally reign it in and wear something from Ann Taylor, but you should make an effort to look like a lady. So what does one wear to such a function? Not to fear: I’ve pulled together a few looks to choose from to ensure the night (and your look) goes off without a hitch.

Look No. 1

Spring and summer are all about the LWD — Little White Dress. You have at least eight months of cold weather the rest of the year to wear your boring old black dresses, so why not take advantage of the nicer weather and lighten up? Warm weather is a good time to wear lace and crochet, too, so combine it all into one with a white crochet mini-dress. But for a night out, your look shouldn’t be all sweetness and innocence: add a little edge with a faded denim motorcycle jacket, cool jewelry and some killer wedges. 

Jacket: Urban Outfitters, $79
Dress: Nasty Gal, $68
Wedges: Aldo, $100
Serpent ring: Urban Outfitters, $24
Turquoise ring: Urban Outfitters, $24
Amber ring: Forever 21, $5.80

Look No. 2

You’ll certainly stand out in neon yellow skin-tight skinnies that are right on trend. A bustier with that? Yes please — I’ll take any opportunity to promote the wearing of bustiers. Add a choker, platform peep-toes with a buckled ankle strap and a sock bun, and you will literally look fabulous, which is not a word I toss around a lot. This outfit shows just the right amount of skin, is sophisticated without trying too hard and is super-duper chic. And in case you were wondering, winged eyeliner and an electric blue or green envelope clutch would really take this look to the next level. Just saying.

Jeans: Gap, $59.99
Bustier: LuLu’s, $42
Necklace: Forever 21, $10.80
Shoes: Nine West, $99

Look No. 3

I know shorts can be scary for some people, but they really shouldn’t be. They are a beautiful thing, especially these shorts. Are the nearly $500? Yes. Do I care? Not really. These pants should be an inspiration to us all: embrace the statement short and put aside negative feelings about your thighs. Cool shorts shouldn’t go un-loved, so find a pair of your very own. And once you do, wear them with a bright silk t-shirt, an arm-load of bracelets and metallic sandals. You’ll be happy you listened to me.

Shirt: JCPenney, $18
Shorts: Free People, $488
Shoes: Zara, $69.90
Turquoise crystal bracelet: J.Crew, $78
Wing bracelet: Forever 21, $8.80
Woven bracelet: Forever 21, $6.80
Yellow bracelet: Urban Outfitters, $120

Photo courtesy of Flickr / himenohogosha.