Best for $20(ish)/Classy by Association

I am a HUGE fan of bargain shopping. Specifically, the T.J.Maxx in the town next to where I grew up, it has the BEST selection ever!  People ask me all the time, where did you get that and are invariably surprised when I tell them- T.J.Maxx baby. It's funny-- no judgment here-- because this town, home to the legendary Maxx, also harbors the least well dressed people in the state, ha, in my opinion. Since moving to NYC, I have explored a number of small vintage shops, flea markets,  etc, here and there, and it's amazing what you can find! I think it's all about mixing and matching, pair the things you bought out of someone's garage with a nicer piece and suddenly, people think you so fashionable and great at mixing styles. Ha, little do they know, you are just broke. There are some rules I adhere to:

1. I try not to be a quality snob-- sure if I look at this $20 pleather shoe super up close, it doesn't look so great. But who is going to look at the shoe that close? No one. Make sure you are not judging things too harshly, from the proper viewing distance they may look great.
2. Nicer and cheaper pieces blend easily. There is no need to feel like you cannot wear a pair of cheap random shoes with a fabulous dress. They key is to make sure you do not look like you are trying to hide it-- people will be like, oh who made your shoes? Jessica Simpson via T.J. Maxx thank you very much. Pair them with something classy and they are classy by association.
3. The great thing about mixing wardrobes is that it allows you to buy things you would normally never commit to. If something is $15, I am willing to give it a try- so don't be afraid to branch out. You never know what might work!
4. If something is bought second hand ALWAYS freaking wash/dry it. end.of.story.

Below are some of my faves for around $20!

Chanel Bag, BK Flea Market, $25. 

Leopard Booties, Necessary Clothing, $20.

T.J. Maxx, $24.99

Ditto. 

Didn't purchase this gem-- though I did think it was fabulous. Couldn't quite picture where I was going to wear it...and it was $30, which sort of breaks the rule.