How to sharply evaluate any new wardrobe purchase

Questions to consider other than “is it cute?”

Shopping and consuming have long been intermeshed with the daily movements of life, almost automatically and involuntarily. We buy out of need as much as we do out of idleness, social expectation, and the need for stimulation.

I often browse online as a sort of mindless, end-of-the-day ritual to see what’s new and what I can pin to Pinterest. About 5% of the time, I see something that I just love and feel the urge to make mine, rather than appreciate but readily pass on.

Unfortunately, I’m not working full-time and don’t have tons of disposable income, so I have to be smart and plan ahead for any purchase over $50.

That sort of discipline is hard to develop solely out of a desire to spend less. For me it’s a necessity, one that has been painful at times but also allowed me to really hone my incisiveness with potential purchases.

More often than not, I walk away from near-purchases (now less begrudgingly) and realize later that I never gave them another thought. As I wrote in December, there will always be something appealing to choose from. No acquisition is truly urgent in the way sellers would like you to believe.


The question “is it cute?” is often the one that gets answered first, since we analyze the visual in a split second. A yes to this question establishes initial interest in an item or garment. But what else should you ask yourself before making a purchase?

Try asking yourself this before any purchase: “Do I really need it?”

Sometimes this comes first, if a valid need initiates the search. But in many moments, need comes after desire, so it’s useful to remind yourself that you may not *actually* need anything.

It’s OK to admire and put back (or keep browsing online).


For most people, except perhaps the top 5–10% of households, price is important. What’s affordable to one person could be unaffordable to someone else, so it’s up to you to decide how much is too much.

If you’re like me, the question of price comes almost concurrently with “is it cute?” because some prices trump even the highest level of cuteness. I try to look at aesthetics (and/or need) first, then brand (for orientation), and then price. But in reality all three happen almost simultaneously.

I could write plenty more about why the lowest price isn’t always the best price and why sometimes paying more is better — item quality, durability, or artistry and supporting local brands and independent merchants — but I know for many people there is a hard limit on what they can and will pay for something for a variety of reasons.


Next, ask yourself: “is this something I would actually wear?”

As in, does it fit with your aesthetic? Does it feel like an extension of your taste or like you’re in a costume?

Are you comfortable wearing it? Walk and sit down in it. Wear it underneath your coat (if applicable).

Does the color flatter you and does the fabric feel good against your skin? Try it in different lighting scenarios.

Does it match with and complement the rest of your wardrobe? Will it make all your other clothing look dated or shabby?

Can you see yourself reaching for it regularly or is it more of a once in a while item?

Is it a color you like and have a lot of already? This can be good if you strive for a consistent uniform, bad if you get bored and like options.

Is it redundant (nearly the same as something you already own) or is it something new and interesting, to add dimension to your closet? If it’s redundant, could it replace something (one in-one out)?

If it is new and interesting, is it a particularly trendy item that may feel rapidly dated?

Do you know how to care for it — will it require dry-cleaning? Is the material delicate or durable?

Within all the questioning above is an inherent need to know and be honest with yourself. If you acknowledge that you put your things through hell or never feel confident wearing white or have previously tried to wear jewelry but just feel like it gets in your way — those truths may change some of your answers.


Next: how does it hang?

This is a more nuanced question, one that has to do with the quality of the material and proper fit.

Some things just hang right and others don’t.

Earlier today, I visited a consignment shop in San Francisco’s Presidio Heights neighborhood. I found two cotton tops from Brunello Cucinelli and a gorgeous angora-blend long coat by Prada, which quickened my pulse.

But I tried them on, and none were quite right. The pullover sweatshirt was a little lumpy. The knit cardigan was too. They were probably both cut for an older, rounder (wealthier) body.

For me (and any guy), the things that have to look good are the chest and shoulders on a top and the butt in bottoms. Not necessarily tight or clingy, but accentuated and flattered. I suppose this is subjective, but anything too baggy looks sloppy to me.

The angora coat was lovely and fit my upper body beautifully, but had over long sleeves. Had it been cheaper, it may have been worthwhile to shorten the sleeves. But at nearly $500, I decided to pass.


Ultimately, it isn’t always obvious if an item is a “definitely” or a “nope.” All garments and worn items are a combination of function, form, and value, so it’s up to each of us to decide which of those factors is the most important.

If you encounter something that checks all the boxes (i.e. is cute and fits well, 100% would wear, and is within budgetary reach), then bravo! Go for it.

Sometimes everything works except price. I run into that a lot because I have expensive taste. I rationalize those purchases by making absolutely sure I love something and will keep it for a while. Plus I stalk things until they go on sale so I’m not paying egregious prices.

Or it’s beautiful and fits well but is uncomfortably loud stylistically, and would end up languishing in the closet because it feels awkward to wear.

No one makes perfect purchase decisions every time.

But too often we let price drive us, so the perception of a deal usurps questions of whether we actually need something, would wear it, and are tickled by it aesthetically.

It’s one reason why Marie Kondo’s tidying trend has hit the mainstream and resonated with so many. We all have too much stuff, only wear about 20% of it, and are slowly killing the environment by making and wearing cheap, plasticky clothing.

We should all be less automatic in our shopping attitudes, and step back to more sharply analyze each time we mindlessly browse online or in person.

Ask yourself some of these questions and you may find yourself doing a lot less unnecessary spending.