The Best Times to Shop (and Why Timing Matters More Than Trends)
- Christen Johnson
- Jan 2
- 3 min read
Christmas was just celebrated, and I have to say — my sister is one of the best gift givers I know.
She knows my taste. She knows my size. She understands my personal style better than most people.
Every year, she somehow manages to gift me pieces that don’t just feel thoughtful — they actually fit into my wardrobe. This past Christmas, she elevated my closet with a few key layering pieces, shoes, cozy loungewear, and even some summer items I’ll be wearing months from now.
And it reminded me of something I talk to my clients about all the time:
The best wardrobes aren’t built when everyone else is shopping — they’re built when you shop with intention, at the right times.
Why Timing Is Everything When It Comes to Shopping
Most people shop emotionally or reactively:
When something goes viral
When the season changes
When they “have nothing to wear”
But intentional shopping looks different. It’s strategic. It’s patient. And it often happens outside of peak shopping moments.
When you shop at the right times, you:
Save money
Get higher-quality pieces
Avoid impulse purchases
Build a wardrobe that actually lasts
Let’s talk about when those moments are.
1. Out-of-Season Shopping (The Secret to the Best Finds)
One of the most overlooked strategies in personal style is shopping out of season.
Buying sweaters in spring. Buying sandals in the fall. Buying summer dresses in winter.
This is when retailers are clearing inventory, which means:
Better prices
More room to invest in quality
Less pressure to “keep up”
Many of the pieces my sister gifted me were technically “off-season,” but they’ll become staples when the time comes. That’s the beauty of thinking ahead. If you already know your personal style and lifestyle, shopping out of season becomes one of the smartest things you can do.
2. Right After Major Holidays
Post-holiday shopping is another sweet spot — especially after:
Christmas
New Year’s
Memorial Day
Labor Day
Retailers are focused on clearing stock, not pushing trends. That’s when you’ll find:
Elevated basics
Classic silhouettes
Investment-worthy staples
Instead of buying what’s loud and new, you’re able to choose pieces that quietly support your wardrobe. This is one of the reasons I always tell women: don’t rush to shop before the holiday — wait until after.
3. End-of-Season Sales (With a Plan)
End-of-season sales can either be a goldmine or a trap — depending on how you approach them. The key is to go in with clarity:
What gaps are you trying to fill?
What silhouettes do you already know work for you?
Can this piece transition into multiple seasons?
If you’re buying simply because it’s marked down, you’re likely wasting money. But if you’re buying with intention, end-of-season sales can help you elevate your wardrobe without overspending.
4. When You’re Calm — Not When You’re Desperate
This one isn’t about the calendar — it’s about your mindset. Some of the worst shopping decisions happen when we feel:
Frustrated
Pressured
Behind
Insecure
The best time to shop is when you’re clear-headed and confident in what you’re looking for. That’s when you make choices that align with who you are — not who you think you need to be. Intentional shopping is a form of self-trust.
5. When You’re Shopping for Your Future Self
One thing my sister does so well is shop for who I’m becoming, not just where I am right now.
That mindset shift is powerful.
Shopping with your future self in mind allows you to:
Build slowly
Invest wisely
Avoid constant closet regret
You don’t need everything right now. You need the right things over time.
What I Received for Christmas
I shared everything I received for Christmas — from layering pieces to shoes to loungewear — over on LTK. Every item reflects my current style priorities: comfort, versatility, and ease without sacrificing chicness.
Intentional shopping isn’t about buying more — it’s about knowing where and when to buy.
If you want guidance on which brands are worth your time and money, I created The Places to Shop E-Guide to support you. It’s a living resource I update regularly, designed to help you shop with confidence and clarity — not pressure.
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