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5 Questions to Ask to Completely Change Your Sartorial Game

Here are the five questions you should ask yourself before inviting a piece back home to your closet.


Our story starts one late Friday night where I, the heroine, have found myself perched on top of a bar stool, trying my best to get the bartender’s attention while biting back the urge to fidget. Again. The whole night was full of it: Little hem pulls here, sleeve adjustments there, and nervous button fiddling scattered through out. Why was I so outside of my element? Because I was wearing  a low-cut, thigh-grazing, absolutely-gorgeous romper, and all I wanted was one of my usual shift dresses. I wanted to try something new with the romper, and so I marched it back to my place in its shopping bag and left the apartment thinking I’d be a changed woman while having the gorgeous number drawn around me.

And I was. I changed into an uncomfortable one.

We’ve all been there before, where we take stock of our wardrobe and give bewildered looks toward at least a quarter of the occupiers. Trends were tried and failed, a few pieces were purchased even though they didn’t fit quite right, more were bought just because they were on sale, and some were apparently bought after a night of not-too-soberly online shopping. So many mistakes, so little closet space.

While they’re not completely unavoidable, we can minimize the usual mistakes by asking a few key questions when out shopping and curating our wardrobe. Honing your sense of style can be a tricky thing. A lot of the times you end up making nonsense purchases, try to make things that don't feel like you work, and hop on trends without any real game plan. This set of questions will help you hone your style and lead you to a more focused, truly-you wardrobe.

Here are the five questions you should ask yourself before inviting a piece back home to your closet.

What Are My Holes?

5 Questions to Ask to Completely Change Your Sartorial Game

Yeah, I see that cactus print dress hanging there. And I agree, it would look completely amazing on you. But riddle me this: Do you have a pair of really good jeans yet? Or how about a neutral pair of shorts you can wear all summer? Classic sandals? A good, black crossbody bag? Before you start buying unique, playful pieces, tackle the foundation of your wardrobe first. Find all the staples you’re missing and begin to slowly fill them. You’ll be thankful for your self control after the fact because then you’ll actually have something to style that cactus print dress with. You’re welcome.

Does This Have Any Remixing Potential?

5 Questions to Ask to Completely Change Your Sartorial Game

Sometimes we get swept away with a truly dazzling find and buy it without thinking it through. It’s like a summer love affair: One moment you’re watching Netflix alone, the next you’re running through city streets during summer evenings, trying to find dark corners to kiss in. It’s wild, and fast, and fun…and usually ends with a bit of a head scratcher.

While those are perfectly acceptable purchases some of the time, the other times try to ask yourself what remixing possibilities the piece has. Can it go with more than one pair of pants? Would it look nice with skirts, maybe layered underneath dresses? Will the color go with the palette of your wardrobe; does the pattern easily mix with other pieces you already own? If you can’t think of at least three other pieces you can remix it with, it would probably be best if you put it down.

Do I Already Own Something Like It?

5 Questions to Ask to Completely Change Your Sartorial Game

It’s never a good thing when you open your closet and it looks like the inside of a cartoon character’s: Just the same type of dress, over and over and over. Try to curb your love for a certain style and use that saved money to buy something different. For example, if you already have two striped dresses, there’s no real need for a third one. Even if it is in a different color. The vibe of the dress is still the same, so keep it moving.

Where Can I Wear This?

This right here will nip a lot of wishful-thinking purchases right in the bud. It’s especially handy for when you’re toying with jumping onto a trend with no real game plan. Do you usually dress minimally and in neutrals, but are sort of obsessed with the ‘70s trend that’s having a moment right now? Is that why you’ve found yourself in a dressing room, turning this way and that, trying to determine if the long sleeved paisley dress is for you? Now, don’t get me wrong, you can definitely pull it off. But the question is, are you ready to? We all move at our own speeds, and sometimes we need to ease ourselves into change. To determine if you are, list at least three places you can actually see yourself wearing the item in question. Imagining yourself sitting there wearing it will either motivate you or help you save yourself from another future donation.

What’s One Thing I Really Love About It?

While in the dressing room, make yourself say one thing that you really love about the piece. And I mean really love about it. Does the color compliment you; is the detailing mind-blowing; do your legs look like something out of a 1950’s movie poster? Does something about it make you feel gorgeous; does the pattern make your heart feel like butter melting on toast? If you end up with a shoulder shrug and a “meh”, then you know you’re just shopping for the sake to shop. If you want a closet full of pieces you truly love and are excited to wear, then these questions will help you stay on track to getting just that.