This particular time when you are still in the heart of a season, but you know the end is coming is just the right time to interview your clothes. At nearly the end of each season, I like to look through the closet and see what I haven't deemed worthy to wear for the last few months. The timing is crucial because you have to have enough season left to test out these neglected items. If you wait until the weather changes, you are likely to look at each item, declare your undying love for it and put it away for next year.
So, just stop right there. Take a look at the pieces you haven't worn and put them aside to wear this week. There is a reason you are not wearing them and we're going to find out what it is.
Here is the strategy. First, take the time to combine new outfits. Maybe you haven't worn something because it doesn't go with anything you own. Try to work it in to what you already have without buying anything new. Be creative with colors or layering. I'm always surprised at the colors that can work well together. Trinny and Susanna's book What You Wear Can Change Your Life has many surprising, but beautiful color combinations. Paint chips are also an interesting (and free!) inspiration for color combos.
Try on your outfit. If it makes it out the door, be aware of how it makes you feel. We are investigating why you haven't worn this item all season. Is the color bad for you? Does it not fit well? Too short? Too long? Does it just make you feel yucky? Is it worn out? Sweater pilling? Stain? Pay attention! Sometimes I have done this exercise only to come home at lunch and put the item in the to-go box. If you realize now why you don't like it, LET IT GO. You have given this garmet it's trial and now it is guilty, so bu-bye.
Always have a to-go bag or box. Someone will be very happy to receive these things! My to-go box contains read magazines, lipsticks that don't work for me, jewelry I don't wear anymore, clothes, products I don't like for some reason. I have various people I donate my things to and it's great! I bring magazines to a friend at work who has a teenage daughter. I donate clothes to a charity unless I know someone in particular who would like them. It really is fun! It's important to keep the FLOW going in your home. Bring it in and take it out.
If you haven't realized it yet, this is actually just a sneaky way to get you to start cleaning out your closet. I know it is hard to get rid of things that you purchased. You may be in "I may need it someday" camp and I understand! I hope this helps you to see that if you don't like wearing it today that you will never like wearing it. This also slows down the closet cleaning process to one item at a time which is a pace that some people need. Evaluate each item based on the strategy above, and be aware next time you are in the dressing room to evaluate the same way. Don't be seduced by a great price or a brand. If it doesn't work for you, let it stay at the store.
On the other hand, now is also the time to fill in the gaps of your winter wardrobe. As you go through your closet make notes, yes literally write it down, of what would be an asset to combine with your current pieces.
The sales are on their last leg here, but you can still find wool and cashmere at great prices. If you need a winter coat, boots, sweaters, wool pants, or winter accessories-hat, scarf, gloves, now is the time to find those things on sale. When I am shopping, I already have a list in my head of what I want/need. I like to be open about the details, but I have guidelines. For example, I need some a couple new wool sweaters and I found a merino wool orange turtleneck at Banana Republic for $18.00. It's perfect because I wanted it, needed it, and found it in a color I can combine with my wardrobe.
Ladies, it's not perfect when you have to reinvent your wardrobe to match the great deal. Beware of having to buy more to work around it. This new item should go with many things that you already have. If it doesn't, be realistic and ask yourself if you are buying it for a fantasy wardrobe that doesn't fit your actual lifestyle.
And this is a rule I always apply. If you haven't worn a new item in a week, please take it back. Spend your money on what you will actually wear. I know it may be lovely or a great deal, but what is the point of it hanging in your closet unworn? This action defies logic, but I have done it and I bet so have you.
The exception to the take it back rule is a replacement. When you are interviewing your clothes, make a note of any item that will need to be replaced within the next year. Maybe they are ok to get you through this season because there isn't much season left, but take advantage that you have almost a whole year to find your perfect replacement. You can shop wisely and be selective when you have so much time.
Most of all, have fun! Editing and acquiring a great wardrobe for yourself takes years. Both steps are required to keep your personal style current and your clothes in good condition.