Is your closet a mess? Do you have a hard time finding outfits to wear despite having plenty of clothes?

If so, you’re in luck, because this is the beginning of a short series on how to sort out your closet issues forever.

If you watch What Not to Wear or Tim Gunn’s Guide to Style, you probably know about the first step already: that’s right, you clear your closet of all the clothes that you don’t (or shouldn’t) wear.

While you’ve probably heard that you should do this regularly, chance are that you haven’t done it. Why? Because clearing one’s closet isn’t as simple as just putting clothes into piles. The real skill is knowing what needs to go and where you should send it – and how to fend off the inner pack-rat.

Here’s some tips to make it much easier.

Getting started with your wardrobe clean-out

There are two ways to tackle a wardrobe clean-out:

1. Set aside a whole afternoon to do it all at once, or
2. Tackle the task a little at a time

Setting aside a whole afternoon to clean out your closet can be a great way to take stock as you can also spend time combining pieces to make new outfits. However, not everyone can schedule a few hours to devote to their wardrobe.

Alternatively, you can break the task into smaller blocks so you can tackle it over a few days or weeks. For example, you might do one category of clothing at a time: start with, say, sorting out all your trousers and jeans; then move onto t-shirts and tops; and so on ’til you’re done.

One way to save time is to start on laundry day before you put away the clothes that you’ve washed. Hopefully everything that you’ve been wearing is both flattering and in great condition. In that case, they all go into the keeper pile while you sort through the clothes that are still in your closet. If there are any clothes you have doubts about, though, keep them out to sort.

Step 1. Get out your clothes to sort

Before you start sorting, get out all your clothes that need to be sorted. The bed is a great place to put them because it’s probably near your closet, and it’s elevated so you won’t have to keep bending over.

Piling your clothes to sort together also helps show you how much clothing you have. You might be surprised how much your closet holds! It can feel much easier to get rid of clothes that you don’t need or shouldn’t wear when you realize how much stuff you actually have.

Step 2. Decide how to sort your clothes

Decide what piles you are going to sort your clothes into and where you’re going to put each one.

I suggest the following piles, but you could break them down however you want:

1. Keepers: Clothes that go back into your closet because they’re awesome, ready-to-wear, and get plenty of use.
2. Storage: Clothes that are basically keepers, but don’t get worn very often (or are out of season right now) so they can be stored elsewhere to free up valuable space in your closet.
3. Repairs: Clothing that need mending, cleaning or tailoring, but would otherwise be keepers.
4. Returns: Clothes that still have tags attached because you’ve never worn them!
5. Giveaway or sell: Nice clothing that’s just not flattering on you but would be great for someone else.
6. Throwaways: Items that shouldn’t be worn by anyone — things that are worn out, badly stained or otherwise unwearable.

You can also make the piles anywhere you want, but having boxes ready for the giveaways and throwaways is a good way to keep them separate, so you don’t accidentally put a keeper in those piles.

Step 3. Sort your clothing

Now you’re going to go through the big stack of clothing on your bed piece-by-piece and move every item to one of the other piles. Some items will be easier to sort than others and some piles will be easier to fill than others.

Take your time, and don’t put anything back into your closet unless you’re absolutely sure that it’s a keeper.

To be sure that a garment is a keeper, ask yourself the following questions — and don’t forget to answer really honestly! An item isn’t a keeper unless you can answer all these questions with a firm “yes”.

Question 1: Is it free of stains, fading and tears?

Stained, torn or badly faded clothes should not be part of your everyday wardrobe.

There’s not much that can be done about fading unfortunately, but you might be able to salvage clothing that’s stained but otherwise fine if you take your clothes to a professional cleaner. Likewise, some tears can be repaired by a professional, but most will mean a garment can no longer be worn.

Some of these items could be useful to keep for painting your house or to use as rags; but most should be thrown out.

Question 2: Does it fit perfectly?

This simply cannot be stressed enough: perfect fit is the key to looking like a million bucks in bargain clothes. Poorly fitting clothes look cheap no matter what they cost. For an example of how to tell if a garment fits, read how to choose tops that truly fit.

If an item doesn’t fit properly now, but would be fantastic if it did, consider having it tailored. While not everything will be fixable, a good tailor can work wonders. They can alter the size, length and fit of garments and even make major alterations like removing sleeves or turning a dress into a top or skirt.

While some alterations are so cheap it would be silly not to do them, very major alterations could cost more than the garment did. Before you have an item tailored, make sure the cost-per-wear will still be reasonable after you’ve paid for the alterations — there’s no point paying for significant alterations to garments made from cheap fabrics that will wear out quickly.

Angie from You Look Fab has written a fantastic list of estimated costs for tailoring in the U.S. If you’re not sure whether something could or should be tailored, remember that it doesn’t cost anything to ask your tailor.

If your weight fluctuates, you might keep “skinny clothes” or items that are a little big, in case your weight changes again. It’s fine to keep these if you can reasonably expect to fit into them again, but don’t clog your closet with them. Keep them in storage instead so that everything in front of you each morning fits perfectly and you’re not tempted to wear clothes that pinch and pucker.

Fit is even more important when it comes to shoes, and it’s unlikely that your shoe size is going to change much, if any, so there’s no point keeping them if they don’t fit.

However, a great shoe repairer can alter shoes to a small degree by stretching, adding inserts or re-sewing them. So before you throw out those gorgeous but uncomfortable designer shoes you found on sale, take them to a shoe repair shop to see if they can be adjusted.

Question 3: Does it look great on you?

It’s a gorgeous color, a fabulous style… but when you wear it, you look dreadful. Don’t keep it; pass it along so someone else can enjoy it.

Can’t tell if it’s flattering? Ask yourself, “Do I look good in this?” It takes a while to develop, but learning to judge whether you look better or worse when you wear something is a skill that will save you from many expensive fashion mistakes.

If you honestly don’t know, grab an honest friend and ask them – or better yet, have them take a photograph. Sometimes it’s easier to judge an outfit from a distance.

You might find that you have lots of unflattering garments because your favorite color looks terrible on you. If this is the case, try wearing small doses away from your face, in the form of shoes or a bag. Alternatively, look for different shades because a variation on your favorite color might look a lot better.

Same thing goes for clothes that are the wrong style. We can’t all get away with miniskirts!

Question 4: Does it suit your lifestyle?

A wardrobe full of stunning gowns would be wonderful to have, but it’s little help when you’re dressing for work each morning!

Clothing you don’t wear every day — like formal wear and out of season items — should be stored away from your everyday clothes.

If you’re not sure whether you wear something often enough to justify it staying in your closet, write the current date on a slip of paper and fasten it to the item or its hanger. When you wear it, mark the date again. The next time you clear your closet, you’ll know exactly how often you wear it.

Question 5: Does it work with your other clothes?

Every item in your closet should be part of at least one complete, practical, flattering outfit. Otherwise you’ll open your overflowing wardrobe some days and find that you have literally nothing to wear.

To see if a garment can make a great outfit, first look in your closet for things that work with it. If you don’t find anything suitable, make a list of the pieces you need and shop for them — but set yourself a time limit. If you can’t find the things you need for a reasonable price within 2-3 shopping trips, save yourself future headaches and get rid of that hard-to-match item.

Step 4. Do something with all your piles of clothing

You’ve gone through your closet and should have several piles of clothes. Now it’s time to do something with them.

First, deal with the obvious piles. Put the keepers back into your closet; find a new home for the storage pile; take the repairs pile to your tailor or shoe repairer; and put your throwaway pile in the trash.

You should just be left with clothing that’s new or in good condition, but just doesn’t work for you. You have several options for dealing with these items.

What to do with wearable clothes that aren’t for you

1. Sell them. If you have some higher quality pieces, you can sell them through a consignment shop. Lower quality clothes can be sold at yard sales, but don’t expect to make a lot of money. Ebay is good for in-between pieces.
2. Donate them. Charities such as Goodwill and Dress for Success would love to have your donations. Your clothes will support a great cause and, if you get a receipt, you may be eligible for a tax deduction. That’s a win-win situation!
3. Give them away. Who doesn’t like free clothes? If you have nice clothes that just don’t suit you, offer them to friends or family. Or offer them online to others in your area on Craig’s List or Freecycle.
4. Swap them. Finally, if you have friends that wear similar sizes, holding a clothing swap is a lot of fun. If you can’t organize a swap party, you can still have fun swapping clothes thanks to swapstyle.com.

How to deal with emotional hangups

Let’s face it, closets tend to hold a lot of baggage – and I’m not just talking about purses. If you’re uneasy about letting something go, when you know rationally that you should, then take a moment to think about why that is.

Are you keeping it for sentimental reasons?

Do you really need to keep your prom dress, wedding dress, or that sweater that your mom knit for you years ago?

Sentimental items can be impossible to give away, but they really don’t belong in the closet with your every day clothes.

It’s OK to keep a few reminders of happy times if you have the room to store them properly. If you don’t, consider taking a photograph of it and keeping that instead. And remember, letting go of memorabilia doesn’t mean that you have to let go of the memories.

Does it cost too much to part with?

If you pride yourself on finding bargains as much as I do, you can probably list exactly what you paid for many pieces in your wardrobe – especially the ones that you splurged on. It can be hard to let something go when you think about what you paid for it. It doesn’t help if the tags are still attached.

Old price tags are a red flag that something isn’t a keeper. Chances are there is a reason that those tags are still there. Fortunately, some stores will allow you to return items for store credit even if you’ve lost the receipt and it’s past the return period. It never hurts to ask.

For the rest of your items, you have to remember that clothes don’t make you any money staying in your closet. What you’ve paid for them is gone. Anything sitting in your closet unworn is simply a waste of space. Either try to recoup the cost by selling those clothes, or just enjoy the satisfaction of giving them to someone that needs them more than you do.

Remember — don’t put anything back in your closet unless it’s ready to wear, no matter how you feel about it.

Next time, I’ll show you how to organize and store your clothing and accessories so you can always find exactly what you need — so stay tuned!

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