Image of Nanette Lepore’s dressing room in her Manhattan apartment. From Elle Decor

Yesterday I spent the day at Take 2 Markets, the premiere women’s recycled fashion event here in Melbourne. Most cities now have these types of fabulous markets where your underused wardrobe items can find new life, and what a great invention these are. It inspires you to look at your wardrobe with an editors eye, and makes it far easier to let go of those hangers on knowing you can turn them into cash. With Autumn just around the corner, now is the perfect time to stop and take stock of just how prepared your closet is for the advancing season. However, if you’re anything like me with borderline hoarder tendencies, making the decision about what can go and what can stay is such a painful process I liken it to extracting teeth.

Rather than telling you to follow the old, “if you haven’t worn it in a year” advice, I’m going to give you the secrets I use to help me decide which pieces are truly my treasures.

Have a goal.

Your goal may be as simple as reclaiming some wardrobe space, it may be saving up for a special treat or overseas trip, or it may just be to make dressing each morning easier. Any one of these goals by themselves is enough of an impetus to get you started, but if you’ve only thought about achieving one of these, you’ll realise that the other two come along as secret bonus goals. What started out for me as reclaiming space, quickly turned into a necessary process to find the spare cash I need for my upcoming trip to Las Vegas.

Break it down.

Before you even start to touch the clothes hanging there, I always apply a little productive procrastination *cough*. Create a tangible vision of your goal, just as you would when window shopping on Polyvore. Whether it is a full blown collage with theme music, or as simple as some key motivational statements written hastily on copier paper; all these things help to solidify the goal in your mind.

Paris Polyvore set created by BKLANA

Give yourself a time line.

Like all good goal setting, having a time line to keep yourself on track and accountable is essential. Your deadline could be set to aim for the next recycled markets (book in & PAY), it could by buying those flights you want a year ahead to lock yourself in, or it could be inviting friends around for a party so your space doesn’t remain a bomb site for the next three months. (I’ll admit, mine is still looking pretty rough with all this redecorating!)

Get your supplies ready.

Having all the hangers, labels, boxes and other paraphernalia you’ll need at your finger tips will stop all those further procrastinating trips to the shops, where you are likely to be tempted by even more “bargains” the moment you step through the door. Think of this as a war on your wardrobe, where dresses that look pretty on the hanger but make you feel like a sad amish school girl, are the proverbial wolves in sheeps clothing. Don’t let those suckers fool you into stealing ground.

Get in the trenches.

The first time you open the drawers or slide back the doors, the size of the task may overwhelm you. But take heart, and look to your plan of attack aka Vision Board, for resolution. Remove each piece one at a time and give it this check list:

Is it dirty, damaged, missing buttons, frayed or pilled?

Is it worth the time and or money investment to repair it? (Keep in mind this isn’t just worth in dollars but in how much happiness it brings you.)

Is it obviously dated and calling it vintage is grasping at straws?

Is it a “wolf in sheep’s clothing”? That is, does it make you feel old, sad, fat, depressed, self conscious when you wear it but you always think you’ll get it right next time?

Was it a mistake? Sometimes our most expensive mistakes are the ones we can least bear to part with. Forking out $400 for a sweater that is a beautiful designer piece but makes you look like a lump, has no place in your wardrobe.  Leaving it there for yet another year because you can’t bear to admit you made such a costly mistake is a bad call. Suck it up and sell it while it is still in style and you can at least recover some of that lost cash.

Does it fit your style personality or just the one you wish you had? This isn’t necessarily a bad thing; in fact I encourage everyone to have a few pieces in their wardrobe that really belong to their alter ego. (Latex gloves anyone?) However, if your alter ego never wears them, not even at home, it may be time to open up that space and allow the opportunity for a new one to develop.

Do you have another one like it? Seriously how many pairs of black pants can you have before you are officially declared “Most boring person at the water cooler”? You only need two pairs in your most flattering cut – one summer weight, one winter weight. Everything else will be below par when it comes to making your legs look as long / butt look as perky, as that Holy Grail of trouser cuts. And here’s an idea; once you have found *the* perfect cut, wear them well and invest in having a local tailor or dress maker replace these for you when the time comes. Fashion for pants may come and go, but the underlying structure of our figures is pretty much a constant.

Will you regret it? This is the BIG question on everyone’s lips. I met a lady at the market yesterday who told me of her biggest wardrobe liberation regret when she moved interstate and gave away her red, 1940′s nurses cape.

You won’t regret it if: It can be easily replaced, if it doesn’t have great emotional significance (weddings etc..), it doesn’t make you feel like a Queen, if it doesn’t play a key role in your secret fantasies.

You will regret it if: You didn’t have those perfect, but thread bare pants copied. If it is the one dress that truly makes you feel like Audrey Hepburn even if it doesn’t make you look like it (confidence and fantasy are a seriously important part of successful style), if you haven’t at least had your photo taken in that cute dress from your school formal – it’s about the memories and what that garment triggers, so get snapping before you toss.

Last Man Standing.

Once you’ve followed this strategy you should only be left with stragglers; those pieces you just can’t make a decision on. This is the point to bring out the big guns to help you cut the ties. Give each piece a realistic dollar value that you think it may be able to bring at the market or on an auction site (factor in what it will cost you in time and effort to list it as well). Add up the total of each piece and decide if that amount would be enough to cover it’s ‘rent’ in your space or even better; just how much you’d rather have that cash in your pocket and a wallet full of possibilities for new clothing love affairs.

You’ll be amazed at how well this works! I’ll be the first to admit that this advice come from a hard won place. Of years and years (…and years) of wardrobe culls that still see me hanging on to my Year 10 formal dress (it still comes out for costume parties). From constantly having to struggle against emotional hoarding tendencies, a constantly changing body shape and bank balance.

Kick off the new season with a new style statement… and the room to find it!