Questions to Ask Before Buying More Clothing

Questions to Ask Before Buying More Clothing

Hello, my beautiful friends! My trip to the UK is already halfway over! I’m learning so many things that I want to share, but am going to keep exploring the topics until I return in June. For now, here’s another guest post—this time by my friend Rachel. It is open and honest and deeply personal. But I also think it’s something many can relate to—and it includes some great questions to ask yourself before buying clothing, at the end! x


Seven years ago, I was a brand new high school graduate incredibly excited to start my next adventure at university. I had decided to live on residence in my first year and tried to prepare myself for independent living. I couldn’t wait for a little sanctuary of my own. I thought I was ready to take care of myself. Unfortunately, like many first-year students, living alone my eating and lifestyle habits changed for the worse.

I couldn’t be bothered to find time to eat well between classes, papers and keeping in touch with friends both old and new. Over the next six years of my education, I found myself using food as a tool to procrastinate, a treat for doing work I didn’t want to do or as a comfort when I felt alone or stressed out. I was so focused on doing well in school that I didn’t take time to exercise or sleep. Self-care was put on the back burner while I focused on grades. Unsurprisingly, the pounds slowly packed on. When I graduated from my post-graduate program, I was 90 lbs. heavier than the girl who was so excited to start university seven years ago. I was about to embark on the next phase of life and I didn’t want my own wellness to come last anymore.

I’ve started a journey to focus on my well-being and I’ve found myself faced with something I never had to think twice about before: clothes. Let me preface this by saying I’m not an advocate for weight loss, weight gain or any sort of “healthy” diet. Instead I want to share my journey to mindfulness when it comes to shopping for clothes at any weight.

Shopping at My Heaviest Weight

When I was at my heaviest weight, I struggled to find clothes I felt confident in that fit my new body. I was also in a new phase of my life, starting my first “grown up” job as an intern at an insurance company. My current wardrobe of sweatpants and leggings wouldn’t work at this organization and I was in the mindset that so many of us get into—I felt I needed to look the part to feel the part, especially as an intern wanting to make a good impression. The week before my first day I went shopping looking for business attire.

It was an eye-opening experience.

I was kind of worried, as I headed to the mall knowing I had gained some weight, but I decided to grin and bear it. I ventured into stores I used to frequent and found a very limited selection of items that fit. Anything that caught my eye was typically too small or too tight, even in the largest sizes. In the change room I struggled to get clothes on, asking my mom to find a bigger size, feeling exhausted. The thought of spending even more time looking for things I liked that also fit and feeling embarrassed in change rooms was overwhelming. I started buying anything that fit, whether I actually liked it or not. I wanted to be done with shopping, so I spent money on multiple items of clothing that didn’t make me feel good, simply because they were the right size.

When I started my internship the following week, I may have looked the part in business attire, but I certainly didn’t feel the part. I was wearing clothing that didn’t give me confidence. I felt like an imposter playing dress up in clothes that didn’t express who I was or what I wanted to say about myself as a young professional woman. I’m not one who believes in following trends or that an abundance of clothes is necessary for happiness, but I do think what you put on your body should express who you are and give you confidence—not the opposite.

So here I was, trapped with a wardrobe I hated that I had spent money on, all because I was frustrated and overwhelmed with shopping for my changed body. Looking back, I wish I had taken more time to do research and find stores that carried clothes for women of any size, places where I could take the time to find pieces I actually liked. If I had invested time instead of buying the first thing that fit, I would have felt more confident in my changed body.

Resisting the Urge to Binge Shop

Fast forward to a year later and I’ve lost 23 lbs. so far. I’m finally taking the time I deserve to focus on my mental and physical health by eating nutritious, whole, plant-based foods. I’m working with a registered dietician at my doctor’s office and my number one goal is to be healthy. I’m trying to be more conscious of the foods I consume, why I’m eating them (am I hungry or bored?) and making space in my calendar for walks in nature and enforcing a semi-strict bedtime. I’m no longer an intern and I’m working at a great company that values work/life balance.

These have all been positive improvements in my life and I feel good to have gotten back on the right track. But I’m still stuck with the same old problem: clothes.

I’m at a point in my journey to health where my clothes are getting loose and I’m feeling the urge to hit up the mall and load up my cart, simply because things will fit better. It’s an interesting juxtaposition to where I was a year ago, when the only reason I bought an item of clothing was because it fit. Now, I want to buy things because I know I’ll have choices. This is a battle I’ve been having internally and I know as I continue to lose weight it will only become more difficult.

Enter Mindfulness

This entire journey has taught me the importance of mindfulness when it comes to making purchases. Looking back, I wish I had done things differently, but this was an important lesson to learn. I’ve always thought of mindfulness as an important part of gratitude, but I never thought to let mindfulness influence how I behave as a consumer. 

At my heaviest weight, I was making purchasing choices out of fear and insecurity. I was spending money on clothes I didn’t necessarily like which also made me feel shame in my spending habits. I felt crushing negative energy from these choices when it didn’t need to be that way. There are retailers who sell clothes for plus size women, some with physical locations and many online. There were options I didn’t know I had, and if I had taken the time to do some research, I could have empowered myself to make purchasing decisions that I felt good about

I want to change my mindset by taking a mindful approach to shopping now that I’ve lost weight. I’m doing my best to wear the clothes I have until they are too big to stay on. My boyfriend’s mom is a seamstress and can take in a few items so they’ll last longer. I know I’ll need to buy new clothes eventually, but I want to make sure I get the most out of these pieces. Wearing these now will give me more time to make mindful decisions when I have to buy clothes in the future. 

It’s unbelievable how much there is to be mindful about when it comes to shopping! As I head into a weekend away, I realize I have almost no casual clothes to wear that fit. Working two jobs, 6 days a week means I’m almost always wearing business casual attire. Realizing this has helped me recognize a need in my wardrobe. Now when I do decide I’m ready to buy new clothes I know to look for a few casual pieces that are made well. 

Another way I’m hoping to be mindful about shopping in the future is by looking at quality and construction. I’ve spent too much money on fast fashion that wasn’t made to last. I’m hoping I can find some quality, ethically-made hidden gems at thrift stores. I’m also going to ask myself four questions before I make a clothing purchase:

  1. Do I actually feel good in this? 
  2. Am I only interested in this for a fast fashion trend? 
  3. Does it seem to be well made? 
  4. Will I get my money’s worth out of this piece? 

I hope by approaching each purchase with these questions in mind, I will feel good about the money I’m spending. In preparation for when I do need to buy new clothes, I’ve been cleaning out my closet and getting rid of items I’ve had around since high school that have been taking up physical and emotional storage in my life. I’m ready to move on from the past and embrace this next journey, with the help of empowered purchasing decisions. 


At 25 years old, Rachel is still figuring life out. She currently works a 9-5 as a marketing coordinator at a charity, with a side hustle in real estate. She’s passionate about animal rescue + putting her hands to work by creating. She lives just outside of Toronto with her rescue dog and two rescue cats. Her number one goal is to move to the country. As for a blog—she’s working on it.

  • Insightful and very well written! It’s so important to remind ourselves to be mindful in every aspect of our lives and to ensure that the things we do, say, practice (and even wear) help us in our journey to self love and self awareness.

  • for many years my salary disappeared in few days then I lost job and must to do a little debt repayment so I understood the importance of budget, dofference between needs and wants and now before buy new things I ask myself some simply questions like: do I already have something similar into my closet? can I combo this with items I already have? How many hours I must to work to pay it? then in some cases I use 24 hours rule,…I love this kind of post because are real and everyone can relate thanks for sharing!

  • I lost 60 pounds when I had to overhaul my eating habits due to acid reflux. I also tried to make do with the clothes I had but some of it was so ridiculously big that I was left with no choice but to buy some new items. (I did have some things taken in to save money but you can only do that so far before the whole piece needs reshaping, which gets more expensive than buying a new piece and donating the old.) I took the same approach you did. I shopped carefully so I could use each piece in as many ways as possible. In the end my wardrobe is much smaller but I actually like and wear it all and that is money well spent.

  • Continue enjoying your trip, Cait!

    Rachel – thank you for this post. I have been trying to put my thoughts into words regarding clothing and you put it so well – you should wear clothes that express who you are and give you confidence. Perfect.

  • A really great and honest post. I strongly recommend tailoring. After I lost weight, I discovered a local tailor only charged $12 to take in dresses. They looked so good too! A question for you, that I’m struggling with right now- how do you find affordable and ethically made clothes? Are there brands you recommend? I shop in thrift stores as my happy medium, but certain items, like athletic shoes, I’d like to buy new.

  • I definitely relate on the college weight gain – my Freshman 15 extended well past Freshman year – and I also had been applying my same eating habits to shopping (i.e. buying things when I was bored or stressed), which meant my closet and I ballooned at the same time. Several years ago I began to reduce my belongings and thinned out my closet, shopping mindfully when needed. Recently, though, those old habits have begun to creep back in, particularly shopping and browsing to avoid other things (even writing my blog, which I love doing). This topic has reemerged on several blogs I consume, so I am grateful for your external inspiration to get back on track. Congratulations on the progress you’ve made so far in your journey!

  • Even though my weight has been rather regular (1 shift to 2 sizes up after a nasty divorce plus single mum hood that left me with stress but little excersize options) it took me 30 years to figure out what I like, how to wear it, and where to buy it with seven y to the world. And still learning at 49….
    So don’t worry if you make a mistake here or there in the first few years :you’re way ahead of the curve ;-)

  • Great post! #1 is my main focus. Do I actually fell good in this? This requires A LOT of honesty. Usually the items is a style that I wish suited me and that doesn’t actually feel good. Or its just on sale (big mistake). I have gotten better at recognizing when the item does not make me feel good, and have saved a lot of money this way. But when does the item make me feel good, or even great?
    I’m still struggling to find my style. In the interim, I am keeping it simple with black, white and neutrals. Jeans, tank tops and cardigans. Its still a journey.

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