Let’s face it, shopping can be grueling.  Maybe it’s fun if you are doing it as a pastime with no real goals in mind like a day spent with friends or to kill time.  If this is you, I’d like your life.  Who has that kind of time to just leisurely go shopping anymore?  For the most part, shopping has become a chore. It takes a lot of bandwidth and a lot of trial and error to find the right things, and let’s be honest, how many times would you even consider the things you do find to be the right things instead of things you just settle for?

I think about this often when I am working for my clients, building capsules, shopping around, and strategizing their buys.  This is my full-time job and it can take tremendous focus and a lot of time.  There is no woman on the planet earth who has the ability to focus this much of her limited hours in a day to seek out clothes.  Not to mention very few women come equipped naturally with the set that took me years of training and experience that I cultivated over 30 years. 

Shopping in-store is a nightmare.  Supply chain issues are certainly to blame, but only to a point.  We can’t shift all the blame there.  Long before the pandemic, retailers were chasing their tails trying to figure out how to get people into the stores instead of shopping online and have now found themselves in this weird position.  On the one hand, they understand they need to cater to the online shopper, especially now that the pandemic made everyone completely comfortable with doing everything from home.  But on the other hand, they’ve created such unappealing physical retail spaces with lacking merchandise, poor size ranges, and unhelpful staff.  People are shocked when I tell them I can count on one hand the number of physical stores I’ve been in since the pandemic began and that I have little interest in changing that anytime soon. 

This is not to say that online shopping, despite the offering being more robust, doesn’t come with its own share of issues.  Online shoppers deal with not being able to touch the merchandise, not being able to get what they need immediately, having to navigate the overwhelm of unlimited choices, endless shipments and returns, and so on.  It’s not a perfect system, but dare I say, it’s the better option given the current landscape of in-store retail.  Be it in-store or online, shopping is hard.  If it is hard for you, you’re normal and that’s what I want to talk about.

How to Make Shopping For Clothes a More Enjoyable Experience

At some point we all learn the valuable lesson, you can’t change other people, you can only change yourself and I think this crucial life lesson also applies to shopping for clothes. If you want to make shopping more enjoyable, or at least more bearable, waiting around for fashion to change will be an exercise in futility. Maybe fashion will change, at some point, but it will be at a glacial pace if it does. If shopping for you has felt like a frustrating slog, a chore, depressing, something that makes you want to pull your hair out of your head, made you feel upset about your body, desperate or bewildered, I have some tips on how to reframe and approach the situation so you might not feel so despondent. The fashion industry and how it gets clothes to you may not change but if you can change your relationship to the experience, perhaps it won’t be so terrible.

Find the Humor

This is an actual comment I sent to my client after viewing a photo she sent me when a pair of pants were so high waisted they went to her armpits: 

“So, you mean you weren’t looking for a strapless jumpsuit?  My bad.  I must have written it down wrong in my notes.”  

We have all been in situations where we try something on and it’s ridiculous.  I mean beyond ridiculous.  Where it’s so bad and so far from what we thought it would look like it’s shocking to the point that we can’t believe it.  This is what happened when my client pulled on a pair of pants and sent a photo.  Who is the woman who could even wear pants with a rise that high?  How tall would she need to be?  We had to laugh at the absurdity of it, which is exactly what we did.  One thing I enjoy doing with my clients is laughing together in situations like this.  Even if it’s subconscious, I think my clients start to realize in these moments that ill-fitting clothes are to be laughed at.  You have to find the humor or you’ll go crazy.  

Situations like this do create setbacks in finding what you are looking for but look at it this way, whether or not you get frustrated, the problem is still there.  you still need to find a better alternative to these horrible clothes you just tried on, but humor at least makes the process a bit easier. Frustration just shuts you down and makes the situation feel world ending, which it isn’t.  It’s only clothes.  When something looks bad on a client I will use funny descriptive things to explain how the clothing makes them look, not how they look in the clothing, there is a subtle yet important distinction that should be noted— the clothing is doing it to them, they aren’t doing it to the clothing.  I recently told a client a drab utilitarian dress made them look like they should be cleaning toilets, or that the back view of their jeans made their butt look like they are wearing a dirty diaper.  By bringing humor to these situations we were not only able to laugh and move on but my client was able to separate herself from the problem and see it had nothing to do with her.  It wasn’t her fault, it was the clothes, which brings me to my next point.

It’s Not Your Fault

If you watch The Handmaid’s Tale on Hulu or have read the book, you know the scene I am talking about.  After one of the handmaids tells a tragic story of being sexually assaulted prior to the United States becoming Gilead, the Aunts demand the other handmaids encircle the handmaid telling her horrific story and slut shame her by pointing and repeating, “her fault, her fault, her fault” because, in this dystopian world, this sexually assaulted handmaid is solely responsible for her horrific tragedy.  It’s gut-wrenching and incredibly f*cked up.

As messed up as it is to use this scene as an example, it popped into my mind when I was thinking about this post because I think we’re all guilty of putting the blame on ourselves when clothing doesn’t fit.  “What is wrong with me?  What is wrong with my body?” we wonder when we struggle to fit into something.  I imagine it like a bunch of women sitting in a circle pointing the finger saying, “her fault, her fault.” When a woman can’t make clothing work, how could it be anything but her fault and the fault of her body?  

Men don’t think this way, just like men don’t think this way when a woman breaks up with them.  When clothing doesn’t fit a man, they move on to the next thing that does.  When a woman breaks up with a man, they don’t wonder what is wrong with them, they move on to the next woman who likes them.  Women?  When a man breaks up with them, they will wonder what they did wrong and what’s wrong with them.  When clothing doesn’t fit, they wonder what is wrong with their bodies.  

A very wise client once said to me, “My body isn’t wrong for the clothing, the clothing is wrong for my body.”  You will not be able to find enjoyment in shopping if you can’t wrap your brain around the distinction in this statement.  You will not find any pleasure in shopping until you accept that there is no sizing standardization in fashion, that sizing is completely arbitrary, means absolutely nothing, and that this will never change.  Until you can psychologically free yourself from this mental burden, the false beliefs about your body and clothing, what sizing means and what it doesn’t, shopping will always have an element of struggle attached to it and there will always be an element of self-blame baked in.

You have got to let this go already. I’m not even going to bother logic-ing this one to death because you know it all already. There just comes a point where you either lean into the fact that what the label says and what your body size is has no direct connection. And as far as how frustrating it is that you can’t count on fashion to be consistent in sizing and you never know what size to buy? What exactly will complaining do about it besides make you more annoyed and frustrated? Like, I get it, it sucks, but complaining about it at this point would be like complaining about the fact that every now and then it rains, or that there are only two days in a weekend, or that broccoli doesn’t taste like Hersey Kisses.

Doing the Same Thing and Expecting Different Results

People say it was Einstein who said that Insanity is doing the same thing over and over again and expecting a different result.  But he actually didn’t say it. The origins of the quote trace back to a mystery novelist named Rita Mae Brown, but that’s just a fun fact, not the point.  

People become creatures of habit even when they don’t yield the results they hope for.  It’s not necessarily the fact that we do this that’s interesting but why we do it that is.  And why we do it varies.  

For some, the devil we know is better than the devil we don’t.  Sure, the store you shop most often is sort of meh but what’s the alternative, shopping at one that could potentially produce worse results?  Who has time for that?

Doing something different isn’t always a guarantee of better.  Similar to dancing with the one who brought you, or the devil you know, people get gun shy after failing too many times and it’s true, people get risk-averse the more they fail.  The more failure, the more that comfy corner feels, even if it’s sort of miserable.

Another reason we do the same thing even though we get the same results of failure is that even a blind squirrel finds a nut every once in a while.  Those who prefer consistency will argue that eventually after keeping at something long enough, you will strike success.  Keep at it the same and you will figure it out.  However, this usually applies to situations that take practice, not situations that prove failure over and over again.  A quote I recently read said:  “if you swing an axe at a tree, you will notice it doesn’t fall down. You do it again with the same results. Now you must be “insane” because you keep on chopping at the tree, and it stubbornly continues not to fall down. Eventually, however, the tree will fall. The trick is: Can you tell the difference between axing a tree, and requesting a handout from a rock?  You can’t request a handout from a rock.”

Basically, to summarize that quote, in order to make shopping more enjoyable you have to figure out when to cut bait and stop fishing, or when, using the quote above, you are trying to request a handout from a rock.  Are you trying to make things work that aren’t working any longer?  Have you stopped trying new things?  Have you given up seeking help?  Are you out of your depths?  Are you spinning your wheels?  Perhaps instead of sticking with something, it’s time to set a new course.

Another reason we stick to the same things over and over again is because we think we’re the problem, not the situation that is. And when it comes to fashion, because so many women believe that all the knowledge about the topic is supposed to be embedded into the DNA of anyone born female, most will just keep at it before changing course. Clearly, it’s a woman doing something wrong because women are just supposed to know this. It can’t be the clothes, it can’t be the store. “I need to go home, I need to learn a new style system, play around in my closets more, learn how to make my clothes work!” Women will overanalyze their wardrobes thinking there is some sort of magical mystery they are missing while all along, will put themselves on some crazy shopping fast, reorganize things, go back to the well. It’s exhausting. And then I swoop in and just say, “Why are you shopping there? Why are you wearing that?” and, click, it all ceases to be a problem.

  If something isn’t working, change the plan, don’t keep trying to make current the plan work.

You Don’t Plan

Speaking of planning, if I don’t shop for clients with a plan, I can’t imagine it would be much easier for you to shop without one either.  A plan is strategizing before you hit the stores, like having an end goal, a vision, a sense of needs.  Abe Lincoln once said, “If I only had an hour to chop down a tree, I would spend the first 45 minutes sharpening my axe.”  I think about this quote a lot when I write.  Writers spend a great deal of their time thinking about what they are going to write in relation to the time they actually spend writing.  

To give you an example of planning your wardrobe, I am preparing mine for spring.  I know the bigger picture of what I want it to look like.  In addition to doing it for myself, I will be doing it for all the clients who will be coming through this season.  For myself and each one of my clients, I will have a clearly mapped out vision solidified and each one will be different.  Just this morning, I started a list of notes on my phone of things I wanted to add to my wardrobe to complete this vision.  I see ideas in my head of the exact types of looks I picture myself wearing.  I have inspirational images in my head, I look for more online.  I get inspired, with ideas.  This is how I create what I am going to wear this season and this is exactly how I do it with my clients.  When I stumble on something that I like either for myself or a client, I run a visual check in my head and try to picture myself or my client wearing it in real life and look at if it fits within the style I envisioned for them or me.

I don’t mean to come across as berating or to shame you because I can assure you, if you are not doing this, you are doing what just about every woman in the world is doing. However, what I am trying to point out is just how far out of alignment what you want and what you are doing could be.  You want a neat, organized, easy-to-navigate wardrobe.  You want to shop with ease.  You want to know what you need.  You want clear direction, but you don’t have any plan?  You are literally throwing spaghetti against a wall, hoping something will stick, and then getting frustrated when only a few strands of spaghetti do stick and all you’re left with is a mess on your wall.  I’m not asking you to devote hours and hours to this because, quite frankly, with all the clients I have to manage, my wardrobe takes a backseat to them all and I usually have are a few minutes a day to think about and manage mine in my downtime.  So this exercise should not be an all-consuming time suck and it should actually be a lot of fun because when you start getting focused when you start building a narrative around your style, you begin to construct a framework for the clothing to live into and that is how the clothing you buy starts to become more than just the things that lifelessly hang in your closet.

Don’t Wait For Things to Be Perfect

Enjoying the process of shopping isn’t waiting for fashion to be perfect, for all of it to align so that you can coast through and find clothes that fit perfectly right off the rack, where there is standardization in sizing so perfect that you can buy sizes as if you are getting triple cherries on a slot machine.  The fashion industry isn’t perfect and there is a lot about it that sucks.  Regardless, you are still an active participant who does get a say in the process, who can still decide if this will be a journey of terrible or one that you make the best of.  Control what you can, do the work you can, sharpen your axe, and maybe order a few sizes the next time you shop online.