How To Be Smarter About Dressing Better

Now that you have your closet all tidy with a few empty hangers just begging to be filled again, it’s time to refill it, but with what? Here’s a story that will help.

Recently, a client decided to dress better.  She had changed jobs, lost 30 pounds,  felt like a new woman…and looked great.  Since all of her clothes did not fit anymore, it was time to reinvent herself, but how?

Here’s what I suggested straight out of my e-book Chic on the Cheap – which helps you put together the wardrobe of your dreams when money is tight.

Establish a budget and then pick only 1 or 2 gorgeous pieces that you love and adore

Black Dress Prada
Black Dress Prada

This sounds simple, but it isn’t.  You see, most of us would NEVER think of spending a lot of money on, say, one dress or one pair of shoes.  We would instead buy multiple items on sale and feel good about getting a deal.  The problem is when we keep filling up our closet with things that are not of the highest quality; they tend to look cheap.

It may sound crazy, but sometimes Neiman Marcus, Nordstrom and the rest of those costly stores have super sales.  They markdown items that you would never in a million years think of buying full price or even looking at. I’m talking about things like a Prada purse, Chanel top or a pair of Tori Burch shoes that can go on sale, big time!

Here’s What happened:

The client had been to a conference where she had seen one of the speakers wearing a simple dress with a shiny buckle that said, Prada.  She thought the woman looked very classy and went home to see if she could find the dress.  It was expensive – $825!   Also, it was a style of dress that she never pictured herself in before. So she left it.

A year went by, and she happened to be back at Neiman Marcus and saw the exact dress on the sale rack.  She went in and tried it on.  It fit perfectly, and she felt beautiful in it because the fabric was gorgeous and it was so well made.

Done. She was going to go for it!

It was still a lot more money than she would have ever spent on a single dress, but she thought of all the ways she could wear it and all the events she could wear it to. Still feeling guilty, she bought it anyway.

This is normal by the way.  If you are not used to buying top quality clothes paying big bucks for an item can be a hard pill to swallow.  You will have buyer’s remorse for a while, so just expect it.  You should remember, though, that if you have picked something classic and simple, a piece that you feel like a million bucks in and know that you can wear it a lot, you will be glad that in the end you went for it.

This client has worn her dress a few times already and has no regrets. She feels it was totally worth the splurge!

Of course, you can apply this same idea to a designer item at a consignment shop or an outfit on e-bay at a fraction of the original cost, but it will take some extra time and effort.

This is just one style shopping tactic of many.  Have you ever done this?  How did you feel?  Were you glad you did? Comment below.

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8 thoughts on “How To Be Smarter About Dressing Better

  1. If it doesn’t fit…. it’s a bad purchase. I can’t buy without trying it on first. Nothing fits because of my height… therefore I don’t buy. It would be worth $825 to buy a great quality dress thats FITS like the dress in the picture. Cost per wear would be pennies if the dress is worn…I would wear it until the dress wore out.

  2. I am sooo the clearance shopper..just waiting for the best clothes to go on sale..then, I buy them, and they end up in my closet..with the tags still attached for over a year…

  3. I’ve always wondered if expensive clothing really is better quality. How can I be sure that what I buy at Dillards or even Nordstroms is going to hold up any better than something from Target?

  4. I actually think a black dress can be a little dowdy looking on older women,unless it’s like a floor length halter.

  5. Thanks Annie! THat is the book indeed. At first I could not think of myself just having those 10 pieces or so that she suggests. But if I use my laundry basket as the litmus test, yep, I probably just wear the few pieces that I love! Have fun. Its such a great challenge and a most enjoyable hobby really :-) Jen

  6. Jen, I think you’re thinking of “Elegance” by Genevieve d’Antoine Dariaux (this is from memory), one of my all-time favourite fashion books! Cheap fashion is like snack food, and it is time for us to eat well. Says G d’A D: “Leave fads to women in their thirties”.

  7. Thank you again – I feel inspired! I will report back over the coming months on how I do on this one. My thing is I am great at throwing things away… and do you know, I tend to throw the sale things!!! Bags and bags of them. I had a rude awakening when a store I frequent changed their loyalty program and told me that I was now a VIP since I spent over $2000 in the last year… And it is the store from which I buy Tshirts etc etc!!! Very sobering! I should have bought like your lady, one 800$ dress and still feel fantastic! I sometimes re-read that old French book How to Be Elegant… The wardrobe she suggests is about 10 items long… and yes, wear them for 2 or 3 years and they might be shabby. As she says, the best compliment a woman can get it when her friends say “I am so glad you wore THAT red dress, as you look beautiful when you wear it”. When do your friends say, I am so glad to see you knowing you have 500 old tshirts in your drawer!

    Best and thanks a bunch more! I am going to London and Paris shopping with my daughter for a few days next week on the way to a work function. She is 19… we CAN NOT wait!

    1. Hi Jen,
      Oh so glad you get this idea. When you mention how easy it is to rack up the money spent on little items spent on t-shirts and casual clothes that are not special hit the nail on the head, it can be shocking! Moreover if you add up your clothing bill at the end of the year it can be crazy when you see how much money you are spending and never feel satisfied with what is in your closet! One thing we like to say is, never buy on sale an item that you would not pay full price for. That way you don’t end up with a bunch of items that feel mediocre. Have fun in Europe. Be picky but give yourself permission to buy those one or two amazing items!

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