How to Shop Smarter: Tips from a Personal Shopper



Do you prefer to shop solo or with a friend?


Although I love the time I spend with my friends, I much prefer to shop by myself.


You see, I’m easily influenced by what someone else says looks good on me. If I come out of the changeroom wearing a piece I’m not really feeling, but a friend says—OMG I LOVE IT—I’m left wondering what it is I don’t see and even consider I might be wrong in how I'm feeling.


Now let’s say I emerge from the changeroom wearing something I’m LOVING but my friend’s face says otherwise. On a good day, I wouldn't care. I'd even be so bold as to prance around in it and tell her how much I love it. But on a bad day? When I’m insecure? And unsure of myself? Well, that could ruin everything.


It doesn’t always happen this way. I don’t always buy what my friends like—but I have on more than one occasion. And that piece of clothing sits in my closet and collects dust because although my friend loved it, I didn't. And now I'm by myself, staring at and feeling guilty about this collection of unworn clothing I bought because other people told me to.


Sound familiar?


Now I'm not saying we all need to shop alone, because that's a pain in the ass too! What I want to talk about is how we can shop smarter, and how we can be a more helpful shopping buddy.


Is honesty really the best policy?


I've been praised for being honest and telling it like it is. When a friend wants an honest opinion, they come to me. But I've learned that my opinion isn't always what's best, especially when it's not my decision to make. Sometimes we should instead be considering what our friend needs–and not what we think they do.


For example, I often see women who make their purchase decisions based on what their friends says, even though they might feel otherwise. I once watched a woman smile at herself after trying on a strapless dress, only to hear her bestie turn around and say, “OH MY GOD NO! LOOK AT YOUR FAT ARMS! TAKE THAT THING OFF!”


She turned bright red, felt ashamed of herself, and ran back into the change room. The friend smiled to herself. I swallowed my rage.


Side note: the world 'fat' being used as an insult is a major problem in our culture and something I want to dig into, but not today.


There are so many stories I could share and I’d still never be able to cover all the ways we can fuck up a shopping experience for someone else. So instead I’d like to provide you with some tips to help make the most of your shopping experience–for you and your friends.


Want to start shopping smarter?


In order to start shopping smarter, we need to change the way we think about shopping. We all have a different relationship with our wardrobe and how we shop for clothing. Just like everything else in life, our shopping habits and wardrobe needs change as our life develops. It's important to assess where you're at and make a decision about how you'd like to shop for this season in your life, regardless of what others are doing. Below are a few examples of where you might be at:

  • You're a new mother. You haven't shopped for yourself in a long time, or even feel comfortable enough in your body to do so. And when you do buy something, it better be cheap because someone is going to spill something on it anyway. You want your style and dressing to be easy. You want to be comfortable and look cute. You don't have a lot of disposable income so you need to work with what you have. Shopping for you is about: putting together an 'outfit uniform' you can wear everyday that you don't get sick of, feel cute and comfortable in, and is easy to maintain financially while the kids are growing up.

  • Your weight fluctuates. Your clothes don't fit. You think shopping isn't even an option because you don't know what size to buy for. You hate getting dressed. You feel insecure in everything you put on. Shopping for you is about: loving yourself enough to dress for the body you're in, right now. Because if you can't love your body now, will you ever? It won't overnight, but we can put in the work everyday. Once you start loving your body, finding clothes you actually want to wear becomes a lot more fun.

  • You're a student. You like to be trendy and keep up with what's 'in'. You spend your OSAP on clothing because class is an everyday runway and you're easily influenced by what people think of you. You buy clothing you don't really like because that influencer on Instagram wears it. Shopping for you is about: breaking the addiction. You already have enough clothes to wear, so it's time to dig into what you really love and what you don't. It's time to kick this compulsive shopping habit while you can.

  • You're a working professional. You have a bit of disposable income. You'd like to dress better and feel more like "you" in your clothing. You are ready to invest in quality pieces that are versatile and will last for a few years. You'd like to stop falling for trends that you tire of quickly. Shopping for you is about: taking the time to curate a quality wardrobe you love and care about.

  • You're newly retired. Your wardrobe speaks to your past life and you want to dress for the next season in your life, but you're not sure what that looks like. Shopping for you is about: experimenting with clothing until you find what feels right for this new stage of your life.

Take the time to reflect on where you're at in life and what shopping might be about for you at this time.


2. Make a list of what you need/want. The biggest shopping mistake people make is leaving the house without a list. Why do we make a list when we're shopping for groceries, but not for clothes? Try this: before shopping, make a descriptive list of both "want" and "need" items and the style criteria they need to follow. Your style criteria is the standard you set for the styles of clothing you purchase.


For example, one of my clients was a great shopper who always had a list, but she didn't always follow her style criteria, because she didn't know what it was. I noticed she was buying tops that checked all the right boxes except for fit; she wasn't wearing the tops that were tight on her tummy but bought them because she liked the style or colour. This was the missing piece of her style criteria: tops that flow away from the body. She has since been successful in all her shopping endeavors.


The only caveats for this step are to a) know what you already have in your wardrobe b) know what you want to add to it and c) understand your style criteria. If you're totally clueless, a closet consultation provides the answer to all three. Below is an example of my wants vs. needs list and the criteria that follow.


Please note: "wardrobe essentials" are bullshit - what I need or want in my wardrobe is different than what you do. I don't believe everyone needs to own a blazer or black trousers if that doesn't apply to their life.


NEED (based on what I keep reaching for but don't have):

  • Replace black pumps (pointy toe, medium heel, comfort sole, side cutout)

  • Black sock booties (last pair had a slouchy zipper, watch out for this)

  • Bralettes in white, tan and black (good quality, one that can replace everyday bra)

WANT (based on the wearable wardrobe I want to build):

  • White tie-front top (silk or cotton - no poly)

  • Bracelet stack (see pinterest for inspo)

  • Rusty red trousers (high waisted, pressed wide leg)


3. Create a budget. Now that you know what you're shopping for, ask yourself what you're able to spend on each item and set your shopping budget. A few variables come into play here like: what if I find everything on my list but my budget only allows for two pieces? My advice is to assess your situation and ask smart questions. Have you been looking for these items for a long time? Do they match your style criteria?


Some say we should always shop within our means, and I agree to an extent. What I will say is this: I've spent over-budget before when I've found exactly what I'm looking for, simply because this doesn't happen often. I'm someone who enjoys fashion and clothing, so this investment won't be lost on me. But because I've gone over budget, I will pay off my balance before shopping again. There are so many variables when it comes to shopping within a budget–if you have a personal question you don't know the answer to and would like a sounding board–I'm here to empower you to make the right decision for you.


4. Set boundaries for your friends. If you decide to plan your shopping trip with a friend, I recommend setting boundaries and asking them to be your partner in crime for the day rather than your critic. Give them the low-down on your list and what you're looking for from them–moral support to ensure you buy what you love! If they are there to make sure you don't spend over budget, don't get mad when they hide that $200 dress you're trying to ration.


A few questions friends can ask to help make a purchasing decision:

  • how do you feel?

  • where can you see yourself wearing this?

  • what do you have at home you can wear this with?

  • do you love it?

  • does it check all your style criteria?


5. Dress yourself accordingly. Have you ever been shopping for a strapless dress, only to forget to wear your strapless bra? A key element to elevating your shopping experience is to dress according to your list. Looking for the perfect pants for work? Bring a top you love and pair of shoes you'd wear to work. On the hunt for the perfect top to go with that new skirt? You best bring that skirt with you! Want to find a cute new top to wear with your favourite jeans? Wear. Those. Jeans! All to often we set ourselves up for failure just by not planning ahead.


6. Try on the damn thing. I will never understand why people do this because it usually doesn't end with a happy purchase! The secret to knowing what you want to buy is feeling good in what you wear. How will you ever know how you feel in something if you don't try it on?! This tip is also a lot more fun if you follow tip number five and dress yourself according to what you're shopping for!


7. Read the tags. We all have preferences when it comes to the materials we like to wear and how we care for our clothes, which I consider part of our style criteria. I've learned that my skin can't breathe in synthetic fabrics like polyester, so I just don't buy it anymore. This has become my biggest challenge when shopping because usually I'll find the top I'm looking for but it will be 100% polyester or a blend of some sort. I've settled on this before and ended up being miserable in what I was wearing because I was sweating and uncomfortable. Cute clothing is no longer something I will prioritize over my comfort and I'm glad I learned this early on.


8. Do you really love it? At the end of the day, what you LOVE to wear will always be what you reach for. Perhaps there was an item on your 'Needs' list that fit your style criteria but you didn't end up loving it. That's okay! Maybe you were wrong in why you thought you needed the piece in the first place and it's time to reflect on your list. Whenever you find yourself in the dressing room grappling with the should-I-or-shouldn't-I conundrum, just ask yourself one question: Do I love this? It sounds simple, but I swear it works every time! You'll be surprised how all the things you love can work together and complement each other without the help of something you thought you needed.


Shopping isn't therapy, and it isn't your fucking cardio either. Those mantras were created to help women justify spending ridiculous amounts of money on clothing they barely wear. We all could benefit from shopping less, and shopping more intentionally.


If I didn't answer a question you have—send me an email and we can chat.

ClosettCandyy is a wardrobe consulting service created by Jesse Whale serving the areas of Kingston, Quinte West and beyond. Virtual sessions are available.
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