Wear these outfits to a cocktail bar

I adore dressing up. For most of my life, I attended schools that had pretty strict dress codes, leading me to get super creative (and often theatrical) in my attire. I’ve since then calmed down, but if there’s one place to get a little festive, it’s a cocktail bar.

Cocktail bars aren’t always fancy, but an air of pizzaz and originality is always present (if you’re in the right place, which you should be). Things are chic, but not exactly fancy. Classy, but not uptight. I’m all for wearing whatever you please, and if that’s sweats or a disco ball shiny dress, go for it. However, you might find yourself sticking out. So the question remains, just what do you wear to a cocktail bar? Here are my favorite looks:

Look 1: The Quirky Kitten

  • A kitschy dress
  • Tights
  • Bright heels
  • Loud makeup

I really dig Zooey Deschanel’s style – on occasion. This isn’t a look I rock constantly, because it’s cute, too cute, almost. However, it’s a fun throwback to when actual speakeasies existed. Here’s your inspiration:

Get the latest in beer, wine, and cocktail culture sent straight to your inbox.
Wear this quirky outfit to a cocktail bar
Get the look: dress, tights, shoes

Look 2: The Simple Dreamer

  • Straight leg, dark jeans
  • Loose blouse
  • Shirt-jacket
  • Ankle boots
  • Minimal makeup

This is a timeless look that you can rock at the office and at the bar. It’s comfortable, timeless, sophisticated, and completely appropriate for an upscale bar. I’m five feet tall and have never met a pair of jeans I didn’t have to tailor – except for my dark straight legs. Why? Because I can fold the material at the bottom and they look like cigarette pants, not 90’s-era capris. Everyone should have one pair. And a tip? Don’t wash them unless you need to. Here’s your inspiration:

Wear this casual look to a cocktail bar
Get the look: jeans, blouse, shirt jacket, boots

 Look Three: The Motorcycle Mixtress

  • A cotton black dress
  • Pleather jacket
  • Knee high boots
  • A bangle
  • Smokey makeup

H&M makes versatile cotton dresses for like, $10. Seriously. Buy one in every color. This look is the perfect mix of Joan Jett meets Fiona Gallagher from Shameless. It’s tough, but still sweet. And best of all, all of these items are things you’ll wear again, and again, and again. Knee high boots are totally underrated because they have a reputation of being tacky. So here’s the thing, get equestrian boots, not heels. One, they’ll be more comfortable, and two, they help make the look subtle rather than rawr. Not that there’s anything wrong with rawr. Here’s your inspiration:

Wear this tough-sweet outfit to a cocktail bar
Get the look: dress, jacket, boots, bracelet

Look, these are only suggestions. No matter what you wear, you’ll be touting the best accessory: a cocktail.

Header image via Shutterstock.com