Guess how much this lambskin leather jacket was and win a prize. I'll give you a hint: It's by Thasken's Theory and was last seen on Lyst for $1598 

Today my best friend and I wandered into my favorite second-hand store after a long leisurely walk and brunch through the neighborhood (and a super intense workout ahhh!) As soon as we walked in I could sense her ambivalence - it was crowded, loud, overfilled to bursting. After window shopping the carefully curated, color-coded racks of a few luscious high-end boutiques it was the sensory equivalent of going into a mosh pit after a spa weekend.

Knowing her as well as I do, I pulled her towards the back of the store and directed her eyes upward. "Here's what I like to do," I said, steering her towards the racks of shoes in our size, "I start with the shoes, then the jeans, and work my way from the back of the store to the front." Not only does it help to have a plan, it helps to really know what you're doing - especially if you're going shopping on a busy Sunday afternoon.

At the end of our adventure I left with this real, designer, blue leather jacket for $75. She came away with a pair of Miu Miu flats, a Helmut Lang wool short coat that I am seriously jealous about, and pair of gold-studded sandals that fit like they were custom made for her and perfect silk camisole by rory beca that I know cost low 3 figures new. Her total is too low to even print here for the jealousy it would induce. Also, there's no point - because it's not like you can get it! But the thing is, I find deals like this all the time. Seriously.

Vintage is one thing - it implies curating a piece that evokes a different style that's characteristic of a moment in time. Something can be brand, new - just manufactured - and still be "vintagey." Second-hand is something different. Either the article in question is somewhat timeless or classic enough not to bend too deeply to the whims of fashion (think trench coat, riding boots) or it's designer and recent but already been owned and used by someone else. This is where people get the ick. Why must something be brand new to be amazing? Designer clothes cost a fortune. It's not like they get used up - it's not an old tube of toothpaste or a dried out mascara tube. These are gently worn, exorbitantly priced items that just happened to be touched a little by someone else.

Once you upon up yourself to the possibility of previously loved items, things that seem out of reach suddenly become much more accessible. Who knows why these treasures need a new home, but they are yours for the plucking if you know where to find them.

Behold - the master plan. I'm regretting this already... If you find a pair of size 9 camel colored flat riding style boots, I call dibs.

1) Go to where the rich people sell their clothes
Rich people are everywhere, in every town. They sell or donate their old clothes all the time. They are rich, they get new amazing clothes. On our shopping adventure my BFF confessed to me that the outpost of this second hand store in her neighborhood sucked, and that was why she was so ambivalent about mine. She lives in the Mission. I live near Pac Heights.  I live where Sergei & Zuck live. She lives where people throw animal blood at the buses. Who do you think has better cast-aways to shop from?

Pac heights women do. They actually buy the  stuff from that previously referenced curated boutique and when they are ready to sell them they bring them here. Last week I found a pair of amazing Celine sandals with chopped open acrylic heels for $18.  A month before that I found an Acme Denim Jacket that fit like it was tailored for me (in the Men's section) for $20. I have a friend who finds the most incredible, classic timeless stuff at a consignment store in the Hamptons when she goes to visit her family. Online has also become a rich and fertile ground - especially if you are looking for something very specific. I am obsessed with The Real Real,  but have also had great success with Etsy and Ebay. I just got this IRO jacket (in timeless navy) but instead of $581 plus tax, I paid under a hundred (everyone gets a 20% off code for their first use but they always have some kind of deal) Ebay and The Real Real both have authenticity, as-advertised refund policies. At The Real Real they even let you return things! I even found these sunglasses used on Amazon for $40. Who knew?

2) Look at labels
I have a rule that when I go to the thrift store I only buy designers or brands I have heard of (with some very, very limited exceptions.) This is just my way of ensuring quality but it works. If you've heard of something and the experienced buyers have vetted it, you get some assurances of content, quality and style. When it comes to new clothes I think this rule is garbage, but for vintage you want to know that it wont disintegrate like a forever 21 knockoff as soon as you wear it out of the house. Or, if you love that Forever 21 shirt know that it will fall apart and make sure the price tag reflects it. I am especially good at finding designer jeans. Since I know my size in jeans for most brands these days, I can scoop up 2-3 pairs at second-hand stores for $20-30 when they have them. It's so easy to find the section in my size and pluck out the washes I like. It also allows me to try styles (like flares) without a huge upfront investment. Also, nobody can tell those Joe's jeans are from 2009 or whatever. Jeans look like jeans.

3) Either go looking for one very specific thing or go with an open mind 
If you can, wear clothes you can try on while still wearing them. Workout clothes are particularly good for this - shoes that are a pain to get off and on are not. If you can't be the person with your pile in front of the mirror, challenge yourself to try some new things. Don't just try on one piece, pull a bunch of stuff and go to the changing room. Maybe you'll discover something amazing you never thought of before! The thing about stock at second-hand stores is the pieces need to be somewhat timeless to compete with this season's (fill in the blank) so you end up with stuff that isn't so fickle to the tides of trends. You may find a new wardrobe staple for a small fraction of what an investment piece should cost.

4) Don't buy anything you aren't completely obsessed-in-love with
Ever. New or used. Rent is too expensive to turn your closet into storage space. I try to follow the rule that if I don't immediately want to put it on as soon as I walk out the door of the store then it's not coming home with me. None of this - Oh, BUT.... it will look good in 5 pounds, or in another season - maybe. Be opened minded but also cutthroat.

5) Don't get sucked in by deals
Everything is a deal, everything. But it's not a deal if the cost per wear doesn't pan out (yes, I calculate this!) Don't buy something you love that's not in your size - that's just masochism. Don't buy it because it's a designer whatever if you don't love it (the world is full of designers! not everything is for me) and definitely don't buy it if it doesn't make you feel amazing and perfect right now. Also, don't buy it if you can't afford it - no matter how good a deal it is. Clothes are an investment, but so is health insurance and a house.

6) Practice the 3 outfit rule
You can absolutely love and obsess about bikinis, but if you're an eskimo you definitely don't need more than 3.  Just kidding, none. The correct answer is none. There are clothes you lust after that don't actually fit your life. Before I buy anything I list 3 occasions with matching outfits I would wear the item with. If I can't do it (and quickly) it's a pass.

7) Buy the old version of the thing that's trendy now
Pretend you knew it was going to be cool and saved it lovingly from you teenage closet (or your mom's like me.) Or don't. Just make the people who paid a gazillion dollars for designer "homages" to them that they are cool, but you have the original. If the 90s resurgence has taught me anything it is that my mom was right and everything comes back again (half her clothes that I now own are being remade by the Reformation as we speak. Half the clothes I remember wearing in highschool are back - who wants odds on JNCO style wide legs appearing in the next decade?) My beloved clogs were found in a thrift shop. There are certain things (trench coats, leather jackets, clutches, boots) that are even better/cooler because they were someone else's first.

I don't know when we as a society decided that reusing things is not "cool" - I think it rocks. I would rather be Molly Ringwald in Pretty in Pink than her in The Breakfast Club any day. Thrifty is so haute right now. And don't even get me started on the environmental benefits of reusing clothes - instead watch this video...

Happy hunting!

PS If I'm forgetting any major rules - let me know in the comments below!