Last year I really leaned into the whole big girl with a big girl job thing and finally made my first designer purchase. In fact, I made a few splurgey purchases last year without any prior planning or intention to do so. And I do feel a tinge of guilt when I reflect on them. Do I use my designer purchases often? Sure! But were they really worth it in terms of cost per wear or general usefulness? Well that leaves some room for debate.

There’s a whole lot of pressure around buying designer pieces once you reach a certain age, earn a certain paycheck or even just decide to label yourself as someone interested in fashion. And sometimes it feels like the only way to relieve that pressure is by biting the bullet and draining your savings account for the “it” item. In my experience, this has often led to the humble conclusion that it is in fact just another bag or shoe, and not, as you previously imagined, the magic piece that completes you.

So today I thought I’d pose some questions to ask yourself when deciding whether that item you’ve been eyeing is a worthy wardrobe investment or an impulsive indulgence you might regret later.

Does it suit your personal style?

This should be the first thing you ask yourself when considering a more expensive purchase. I’ve often regretted purchases that were a bit too different from what I know and like to wear. These are usually items in a color or cut I don’t often like wearing - something that’s slightly off but I justify it for other reasons. This happens more with inexpensive items for me usually but it’s a good thing to be aware of nevertheless.

Does it go with other items in your wardrobe?

This is not to say you can only buy designer items in black, white or brown. Rather, this investment piece should be able to work well with its wardrobe counterparts. Take inventory of what you already own so you have a mental image of the pieces in your closet. That way, when considering a new addition, you’ll be able to pair it with several outfits you already have.

Is it a repeat purchase?

When adding items to your wardrobe, one good rule of thumb is to ask yourself if you already have the same type of item in the same color and if you need more than one. And sure, some items might require owning slight variations in size or shape, like a plain t-shirt. Others, not so much - no, you probably don’t need three [insert weakness] because you hardly wear them enough to justify owning one, Jessica!

Can you find it secondhand?

The answer is almost always yes. The gratification of finding it discounted is immense. But this strategy does come with a wait period, which leads me to my next question…

How long have you thought about this purchase?

All pricey purchases require an incubation period. This can range from a few weeks to a year depending on your budget, priorities and how you’re planning to purchase it. Also consider how many other pricey purchases you’ve made in the year. I’m just saying, it’s easy to lose track of how many times you say, “eff it, treat yo self” after a long week.

How many hour did you work for it?

As someone who works in the nonprofit sector, this number is often shockingly high and snaps me right out of my wishful thinking.

Would you pay full price for it?

I remember reading this somewhere and thinking about how often the answer is no for me. Often, I’m more tempted by a good deal, not taking into account that it’s still more than I would normally pay for that type of item. This question is especially useful during the sale seasons and when filtering through those pesky promotional emails. It’s 2020, do yourself a favor and unsubscribe from that inbox temptation.

Can you imagine using it in 2 or 5 years?

Taking into account cost per wear (how the cost decreases every time you wear an item), is super important to determining the value of an investment piece. But one thing to look out for is how trends are influencing your judgement and how likely you are to continue using it 2 years and even 5 years down the road. The more classic and simple a piece is, generally the longer you will want to use it. On another note, if you love something just wear it whether it’s “on trend” or not - but keep in mind, there will inevitably be many more things you will want in the years to come.

When to Splurge on Your Wardrobe