My Annual Shopping Spree at Dillard’s

For the past 7 or 8 years I’ve gone shopping on Jan 1 at Dillard’s, and I usually buy the majority of my clothes for the year during that one sale.

I don’t think I’ve ever walked out of Dillard’s from a Jan 1 sale with less than 15 items of clothing (usually 20 or 25), and I don’t think I’ve ever paid more than an average of $20 per item that would normally have cost $60 to $100.

Even better, because they have so many name-brands to choose from, I can be 10 times more discerning than any other time of the year when shopping for clothing.

  • $60 Levi’s jeans for $20? Not when I can get $150 Armanis for $28
  • Dress shirts I buy range from $12 to $26 and I only buy brands people don’t bat an eye at paying $75 to $150 for any other day of the year.
  • I rarely even bother giving my kids clothes for Christmas any more because I know I won’t find a better deal than what I find for them on Jan 1st.

As I was walking out of the store feeling like Santa with a huge bag of goodies slung over my shoulder, I realized something…

Finding a good deal on vacations is a lot like shopping.  

Sure, you can “wait until you’re ready” to search for flights to Cabo like everyone else does, and you can pay what everyone thinks is a good price.


  • If you can be flexible on where you want to go,
    • you could find flights and an all-inclusive resort for the exact same price as what procrastinating travelers pay (if not less).
    • you could fly to Belize or Aruba AND stay for 7 nights for even less than what most people pay for a flight alone to Cabo.
    • Depending on how long you’ve got for a vacation, you could spend even less for flights and lodging for a couple weeks in Europe or Asia.
  • Much like buying summer clothes during winter sales, if you plan vacation time around when you find an amazing deal (vs expecting to find an amazing deal to a specific place at a specific time) – you can save mind-boggling volumes of money. (That only works if you plan ahead though.)
  • Decide to try a new credit card once a year in return for 50,000 to 100,000 frequent flyer points, and the game changes even more.

Make the following 3 things a priority and I promise — you’ll save more on your next vacation than you ever thought possible.

  1. Watch for deals every day. (Don’t have a system for finding deals every day, and don’t want to pay for my premium service that does it for you? Here is a blog post about how to do it yourself for free.)
  2. Don’t look for trips that fit your vacation schedule. (That’s a sucker’s bet, and you’ll lose more times than not.) Instead, find trips that are 75% to 98% less than you were expecting to pay and adjust your vacation schedule to take advantage of them.
  3. Be flexible on when & where you’re willing to go. (Sometimes, this can be as simple as going from Thursday to Thursday instead of Saturday to Saturday.)

(Extra credit): Throw your old point-earning card in a drawer, get a new credit card that will give you bonus miles worth $1000 to $4000 just for spending 20 minutes switching to their card, and save your newfound miles for a rainy day. You never know when those miles will come in handy, but there will come a day that you really need them, and you’ll be kicking yourself if you don’t have them. (You know what they say about planting a tree…)

1 reply
  1. Veronica Tebbe
    Veronica Tebbe says:

    All good comments! It makes me laugh when people struggle over if they want to spend an extra $2 for a steak but don’t blink at paying stupid prices for flights and vacations. I’m only disappointed for missing your deal for 40% off yesterday!

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