Why Do You Hate Getting Dressed?

Your alarm goes off. You get up, shower, brush your teeth, do your hair and maybe a little makeup. You shuffle into your bedroom and open the doors to your closet and sigh. Ugh. Another day, another outfit, am I right?

It’s a sentiment that’s all too common among my clients: You wear the same outfits over and over again and even those outfits aren’t particularly inspiring. Maybe you do have some great pieces, but they’re sandwiched in between other things you bought or wear out of obligation or just really don’t care about.

Maybe this has only been true for you for a couple of months; maybe it’s been years. Either way, I want to help you resolve it. But, we can’t resolve a problem without knowing what it is, so:

Why do you hate getting dressed?

You’re shopping for someone else.

It’s a tale as old as time…you’re at the thrift and you pick up a shirt that would be perfect if you just replace the buttons. Or you find a dress on TheRealReal that would be perfect for a gala. Or pants by some cool new designer that would look great with 5” heels, otherwise they drag the ground. But you don’t know how to sew…and you’ve never been to a gala…and you only wear flats. So, who did you buy that for?

I’m a big believer in dressing for the life you want, but, sometimes, we let the dreams of our fantasy selves overshadow the needs of who we are right now, and when we do that while we’re shopping, we end up with a wardrobe full of stuff that makes no sense for our lifestyles and that only exists to make it harder to put together practical looks.

Take the time to parse out what actually works for the way you exist, now. That doesn’t mean stop dreaming of a world where you’re chauffeured around in your own Rolls Royce by a 6’5” model who brings you your favorite snacks, just remember that, while you work on that, you still need practical shoes to wear while you walk to the train.

You’re rushing.

I am no stranger to standing in front of my closet at 8:56am when I need to be somewhere at 9:00, and you probably aren’t, either. But, much like having no time to cook can lead to scarfing down fast food that makes you feel terrible later, having no time to get dressed can lead to outfits that make you feel…blah. When we’re rushing, we don’t have time to try tucking in our shirt differently to make it work with that skirt; we don’t have time to try a new method of layering necklaces; we don’t have time to come up with something new so, we end up going with the same old-same old and, if this is a regular occurrence, the same old-same old was, too, born out of being pressed for time.

You’re going to have to start planning ahead. Now, that doesn’t mean laying out your outfit the night before like it’s the first day of school—unless you want to—but, rather, you need to have outfit ideas already solidified so you can just go right to them whenever you’re in a time crunch. Some people do this by trying on the looks, taking a photo, and saving the photos in an album they can always access for inspiration. Others—like me—group pieces they’d like to wear in the coming days or weeks together in their physical closet. Being able to get dressed on a dime is one major reason I suggest regularly taking the time to try on and experiment with new ways to style your clothes to keep your juices flowing.

You’re playing it too safe.

I don’t blame you, I blame fashion magazines. Perhaps, for many, living in poverty is also to blame. Either way, it all leads to the same result: your basics are too basic, whether you’ve followed one-size-fits-all “capsule wardrobe” advice or because financial insecurity makes you hesitant to take risks. This is something that starts while shopping, but quickly snowballs into a closet full of “whatever.”

Before you buy something again—whenever that may be—consider what it adds to your wardrobe: is it a bland “foundational” piece you’re buying because you think you need it or is it something you’re actually excited about owning and wearing? Even your actual everyday pieces don’t have to be conventional: my version of “jeans” is a full, pleated skirt.

Something that “goes with everything” doesn’t have to be neutral, nor does it have to be “classic,” it just has to fit into your tastes and wardrobe, and if you’ve already got a wardrobe full of blacks and tans and greys, it’s even easier to start buying pieces that stand out but still work, just add some color, or print, or texture, or new silhouettes.

You’re “saving that for a special occasion.”

As someone who gave up pants years ago and only wears skirts, I’m very used to hearing “what are you all dressed up for?” when I’m just making a coffee run or picking up an embarrassing medication at the pharmacy. Because my personal idea of casual is a bit dressier than most, there are very few things in my closet that I wouldn’t pull out for a regular day—even my fringe vest has been worn on a hike. And I attribute this act of clothing equality to why I have so much fun getting dressed.

Think about it: limiting yourself by arbitrary ideas of what’s “too much” or even being too scared to “ruin” a piece simply by wearing it is, you know, really limiting. And if the rest of your closet suffers from the issue above of playing it too safe, it’s probably really boring, too.

You don’t have to wear a corset to Costco, but, reevaluate your idea of what a “special occasion” is. Does it have to be a wedding or a birthday dinner or can it be, you know, taking yourself out for lunch? Or, could you dress it down? Can those cool dress pants be paired with a T-shirt? Can you toss a casual jacket over that dress?

Remember, no one has ever laid on their deathbed and wished they dressed down more often.

You don’t know what you have.

I’ve dealt with dark and impossibly cramped closets, small closets, and even no closet at various points in my life, but, by far, the worst to deal with is an unorganized closet.

Now, don’t get me wrong, I’m not saying I have all my skirts organized by length and my shirts by color and my coats by weight and my shoes…at all—I’m just saying any closet where you have to dig and fight to find what you’re looking for—and therefore, often forget what’s not readily at hands’ reach—is an ineffective one.

There’s some easy improvements, though. Like, if you have two levels in your wardrobe, put your bottoms on top and your tops on the bottom since, usually, it’s easier to recognize things like skirts and pants from the hems and much quicker to recognize shirts from their straps/sleeves or collars/necklines—this puts those at eye level.

I also find it useful to put the things I wear the most (typically out of convenience) in a slightly harder to reach spot than the clothes I’d like to wear more. This can force you to focus more on what’s getting used least, especially if you’re like me and you’re too lazy to go in the drawers under the bed where you keep all your T-shirts.

That said, I think life would be easier for us all if we had, like, Cher Horowitz’s closet app from Clueless.

Ooh, and if we had, not just that, but also, like, a stylist could actually come in and style your own clothes right in the app and even provide some recommendations for items you should consider adding to your wardrobe to get more use out of what you already have.

Luckily, we do have such an app! And it’s called Indyx.

I am not making money to tell you to go download Indyx and start cataloging your wardrobe. However, if you want me to look at the clothing you’ve catalogued and style it as well as provide some (optional) suggestions for new pieces to take your wardrobe to the next level, you totally have that option!