
2) Leggings
Leggings of different material and designs are a hot comodity in Hollywood and on the Runway. Sticking with that eighties theme the carzy leggings are making a comeback. From sequined leggings, PVC, pleather and cut out leggings are everywhere. These can be worn with t-shirts, occasionally, and look great with Grnadpa sweaters and dresses. if you're a bit on the insecure side like myself just stick with your plain balck cottone leggings and you'll be good to go. For patterened and plain i would grab them at American Apparel.
3) Ankle Boots 
I love ankle boots beacuse they're so versatile. Throw them on with a pair of skinny jeans, a romper or leggings and then your outfit is complete. You can also get flat boots that are amazing with studded detail if you're not a fan of heels. They are kind of a play off of combat boots but more fashion forward and feminine. You could just go to your favorite shoe store and pick some up for a resonable price.
4) Boyfriend Blazer

This is a great look for every body type because you can get a blzer that is a bit more tailored to make the loom les boxy. Throw it over a an oversize graphic tee and leggins or a fitted shirt and skinny jeans to complete your look. If you're a candaian like myself i would go to Aritzia, H&M is always a great place to look for trendy styles that are inexpensive.
5) The Bag

I am a huge fan of the army canvas messenger bags. I own one and to put your own spin on it you can sew patches and and buttons. This sounds childish but it just adds a unique look to any outfit, day or night. Gap sells plain messenger bags that are fine (where i got mine) but if you want the real thing I would try a thrift store or an army surplus store.