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How I Decide When It’s Worth the Splurge

The 4 questions I ask myself before spending—and 5 things that passed the test.
by Susan Feldman October 2, 2026
How I Decide When It’s Worth the Splurge

I look at a LOT of clothes, and if you’ve been here for a while, you know I’m a big believer in mixing high and low. I will happily wear an inexpensive tee with an investment jacket and never think twice about it. But every once in a while, I find something I’m willing to spend more on. So how do I decide when something is actually worth the splurge?

I have a pretty simple test. Will I wear it over and over again? Can I dress it more than one way? Does it work with things I already own? And—this may be the most important one—do I put it on and immediately feel GREAT?

Because I’ve learned that the most expensive thing in my closet isn’t necessarily the thing with the highest price tag. It’s the thing I bought and never wear. On the other hand, something I wear constantly can end up costing practically nothing per wear.

So I pulled five things that check all of my boxes. They’re not inexpensive, but these are the kinds of pieces that remind me why sometimes spending a little more really can be worth it.

All of our recommendations are curated by Susan & the In The Groove editorial team. In some, but not all cases, we receive a small commission for leading you to what, how, and where to buy all this wonderful stuff.

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Susan Feldman

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