Five Things I Consider Before I Buy Anything
I’m Not Put Off by Bad Photos — And Other Things That Guide What I Buy
1. Context matters
I’ve been thinking about this a lot recently, especially when it comes to those purchases we’re a little on the fence about but can’t seem to walk away from. When you see an item while shopping, whether that’s on a shelf at the thrift store, online, or hanging on a lonely hanger in a designer boutique, context matters. Similar to what I wrote here, how you see an item, and how you experience it in your day to day life within the context of your existing wardrobe is a deciding factor. When we see a beautiful item, we go all googly eyed, only to get it home and realize wait, WTF am I gonna wear this with? The same is true about those pieces that you think to yourself, this is weird, this is odd, but nonetheless, something is there.
The context in terms of how you style a piece can totally transform its appeal. For example, I bought a silk shirt/jacket recently from Poshmark, and when I showed my husband the image he made a face (you know the one). He didn’t get it. First of all, that’s ok. I didn’t need him to like it in order for me to enjoy it, and second, I also knew he couldn’t see the context in which I would wear it. Sure he might still not have gotten it after it had arrived, been steamed and styled to my taste, but sure enough, when I wore it out to meet a friend he commented on my beautiful jacket and how nice I looked. Being the smug twat that I am, I couldn’t help but remind him twas the same jacket he wasn’t sure about when I showed him online days earlier.

2. I’m not put off by ‘bad’ photos
This is another reason why shopping second hand online is tricky to navigate for some. When you see an item unlovingly and haphazardly shoved on an ill fitting hanger, that hasn’t been steamed/hasn’t been stuffed, it makes sense your first instinct is to pass, but being able to read a badly taken photo is a skill you can learn. Ask questions, use Google image search to see if you can find additional photos of the item being worn, or how it looks when it has been cared for. Spend some time considering the potential. Yes you might have to get a handle replaced on a bag, or hem a pair of pants that looked shorter online, but don’t discount a great item just because of how it was shot. Look at the fabric composition, research the brand if you haven’t heard of them. Your wardrobe, and your wallet will thank you for it. Bad photos can be a blessing and a curse, not everything you buy will be the gem you hoped it would be, but then some treasures shine much brighter IRL.

3. I focus on the fit I want, not the size
I know this is old news at this point, but it’s taken me forty years to truly comprehend that knowing my measurements is far more helpful than knowing my size. Not only will it help you shop smarter online, when you can’t try clothing on in person, but it also removes some of levity we place on sizing. And generally speaking, what seals the deal for me is always the fit. It’s normal for me to buy trousers one to two sizes bigger in order to get the fit I want, versus the fit i’m being marketed to want. Shopping for the fit you want is another way to add some personality to your closet, and the easiest way to create interesting proportions. Now that i’m also on first name terms with my local seamstress, I have a better understanding of what can and can’t be done to garments. This alone has changed how I shop, especially with regards to vintage Levi’s. For thirty bucks she can take in the waist and the butt ensuring I have the perfect pair of jeans I want every time. Considering a lot of pairs were thrifted for less than $15, i’m still coming in at around about $45 for a custom pair of jeans made to fit my body, versus trying to squeeze myself into a size that isn’t comfortable.

4. I factor in practicality & comfort most of the time, but I also don’t save things for best
With the odd exception (hello ‘dinner shoes’) I want to wear the things I own. That means I have to get honest with myself about the day to day scenarios I need to dress for, and where I live. I always say, my main goal is to wear the hell out of my clothes, and in order to do that, they need to work with me, not against me. I want comfort and style - and I believe that for the most part I get to have both. Living somewhere warm most of the time means buying thick wool coats (plural) just doesn’t make sense at this point of my life. I’m also ok with the fact that I probably own a lot more leather flip flops and sunglasses than most people. That being said, I also think one of the reasons I’m good at wearing the majority of my wardrobe is because I don’t save things for best. I’m happy being ‘overdressed’ if that’s how it comes across to others, and I try not to seperate my wardrobe into formal or informal wear, because again ‘context matters’. A white tee can be both informal and more formal depending on what you pair it with.

5. Can I afford it?
Look, i’m no saint, but it is an important question. No one needs to go into debt to look good, myself included! Some items in my wardrobe I had to save up for a long (long, long) time, and in many ways the longing for them was part of what made it so special when I did get them. We need to normalize this. There are also pieces i’d rather find a cheaper alternative for. I have written how I (generally) prioritize my spend when it comes to my wardrobe but I can’t lie and say that how much an item costs doesn’t factor into my decision making. It does. It’s another reason why I’m a big second hand shopper because i’m able to buy a lot of higher quality items at a better price point. We each have our own understanding of what quality means, and how much we are willing to part with for a particular item. My interpretation of quality is rooted in longevity, and something that’s well made, which more often than not isn’t always reflective of the price tag. Building a wardrobe you love isn’t a quick fix, and it isn’t something you have to rush.
What would you add?
Thank you so much for reading
Harry x
*Some links contain affiliates and gifted items are marked with an *. You can Shop My Wardrobe here and learn more about The No Buy Styling Course here.



The ability to see beyond the bad photo is the difference. It takes practice an imagination and I think haven’t tried on a lot of clothes helps. Every outfit in this post by the way 🔥
This was so helpful.