When John Lewis Prices Make Me Question My Life Choices (And When They Don’t)

I’m sitting in my Boston apartment at 7 PM on a Thursday, staring at two blazers hanging on my bedroom door like they’re about to render judgment on my financial decisions. One is from Target – cost me $45 during a moment of optimistic budget consciousness. The other is from Theory – $295 that I justified by calling it “an investment piece” while my credit card wept silently. The Target blazer already has that slightly rumpled look that screams “I cost less than your lunch,” while the Theory one still looks crisp after six months of regular office wear. This whole scene is giving me flashbacks to shopping in London during business school, when I’d stand in John Lewis agonizing over whether to spend £80 on a proper blazer or grab three questionable ones from Primark for the same price.

You know what’s funny? I’ve been earning a decent salary for years now, and I still have panic attacks in expensive stores. Not because I can’t afford things – I can – but because growing up with parents who drilled “value for money” into my head means I physically cannot buy something without calculating cost per wear in my head. It’s exhausting, honestly.

But here’s what I’ve learned after a decade of corporate shopping mistakes that would make a financial advisor cry: sometimes the price jump is absolutely worth it, and sometimes you’re just paying extra to feel superior to your past self who shopped at cheaper stores. The trick is figuring out which is which before you’re standing in your closet questioning your life choices.

Let me tell you about my Great Blazer Experiment of 2019. I was new to my current job, trying to build a professional wardrobe that wouldn’t make me look like I was playing dress-up in my mom’s clothes. I bought five blazers at different price points – one from Target, one from Banana Republic, one from J.Crew, one from Theory, and one from Brooks Brothers that cost more than my monthly Metro pass. I wore them in rotation for a year, noting how they held up, how they looked after dry cleaning, whether the shoulders stayed structured or went limp like overcooked pasta.

The results were… illuminating. The Target blazer started pilling within a month and developed this weird pucker at the shoulder seams that made me look like I was perpetually shrugging. The Banana Republic one was fine but unremarkable – it did its job without inspiring any particular confidence or compliments. The J.Crew blazer was lovely until it went through one too many dry cleaning cycles and came back looking like it had been defeated by life. The Brooks Brothers one was beautiful but so precious I was afraid to actually wear it regularly, which defeats the entire purpose of owning work clothes.

But that Theory blazer? That thing has been my ride-or-die. It fits perfectly, holds its shape, makes me look competent even when I’m having an internal breakdown about quarterly projections. I’ve worn it to presentations where I needed to look authoritative, to networking events where first impressions mattered, to dinners where I wanted to look put-together without trying too hard. At this point, I’ve probably worn it 200+ times, which brings the cost per wear down to about $1.50 and falling.

So when it comes to work staples – the pieces that form the backbone of your professional wardrobe – I’ve become a firm believer in paying more for better quality. Not because I’m fancy, but because I’m lazy and busy and don’t want to replace my entire work wardrobe every year. That Theory blazer has probably saved me money in the long run, plus the time and mental energy of constantly shopping for replacements.

But (and this is important) I’ve also made some spectacularly expensive mistakes that taught me price doesn’t always equal value. Like the $400 designer jeans I bought during a moment of “I’m a successful professional, I deserve nice things” that were so uncomfortable I literally never wore them. They’re still hanging in my closet with the tags on, silently mocking my judgment. Or the $200 silk blouse that looked gorgeous in the store but required such specific care that wearing it became a whole production involving special hangers and prayers to the dry cleaning gods.

My friend Sarah, who works at a fashion magazine, has this theory that there’s a sweet spot for most clothing categories where you get maximum value for your money, and going beyond that point is just paying for bragging rights or marginally better details that don’t actually improve your daily life. She’s probably right – I mean, she gets to see clothes at every price point and knows what actually justifies the cost versus what’s just clever marketing.

Take shoes, for example. Cheap flats from Target or Payless (RIP) are basically foot torture devices disguised as footwear. I learned this the hard way during my first year working, when I bought three pairs of $20 flats thinking I was being smart and budget-conscious. They gave me blisters, offered zero arch support, and started falling apart within weeks. I was essentially paying to damage my feet, which seems counterproductive when you think about it.

But once you hit that $100-150 range – Cole Haan, Clarks, even some of the higher-end Target collaborations – the quality jump is dramatic. Proper arch support, materials that don’t immediately give up the ghost, construction that can handle daily wear without surrendering. Going beyond $200-250 for everyday work shoes can be worth it if you have specific fit needs or walk a lot, but often you’re not getting proportionally better quality.

I made this mistake with boots last winter. Bought a pair of $350 designer ankle boots because they were “investment pieces” (I really need to stop using that phrase to justify purchases). They were beautiful, sure, but not meaningfully better than the $180 pair I’d been eyeing from Cole Haan. Both would have lasted equally long, both looked professional, both kept my feet comfortable during long days at the office. I basically paid an extra $170 for the privilege of owning a fancier brand name, which… okay, fine, sometimes that matters to me, but I should be honest about what I’m actually paying for.

The most dramatic quality difference I’ve experienced is probably with outerwear. Boston winters don’t mess around, and a cheap coat is basically useless once the temperature drops below freezing. I had this tragic wool-blend coat from H&M during my first winter here that was so thin I might as well have been wearing a stylish garbage bag. Wind cut through it like it wasn’t even there. I spent that entire winter being cold and miserable, layering sweaters underneath until I looked like a professional marshmallow.

Finally bought a proper wool coat from Nordstrom – cost about three times what I’d been spending on coats, but the difference was immediate and dramatic. Actually warm, wind-resistant, structured enough to look polished over business clothes. I’ve had it for four years now and it still looks almost new, even though I wear it constantly from November through March. That’s the kind of price jump that makes sense – I was paying for actual functional improvement, not just brand prestige.

But here’s where it gets tricky: I’ve also had great luck with some cheaper pieces that punched way above their weight. I have this $30 sweater from Uniqlo that I bought on a whim during a lunch break three years ago. It’s held up beautifully, gotten tons of compliments, and become one of my go-to pieces for casual Fridays. Meanwhile, I have a $180 cashmere sweater from Banana Republic that started pilling after two wears and now lives in my “clothes I regret buying” section of the closet.

Sometimes the expensive option really is better. Sometimes the cheap option is perfectly adequate. And sometimes – most frustratingly – there’s no way to know which category something falls into until you’ve owned it for a while. It’s like gambling, except instead of money you’re risking your professional appearance and comfort.

My approach now is pretty strategic, which probably shouldn’t surprise anyone given that I work in finance. I invest in pieces that have to perform specific functions – outerwear that needs to keep me warm, shoes I’ll walk long distances in, blazers and dresses that need to look crisp through long workdays and multiple dry cleanings. For these items, I’ve learned that spending more upfront usually saves money and frustration over time.

But for trend pieces, evening wear I’ll rarely repeat, or casual clothes that don’t need to meet professional standards, I’m much more willing to take chances with budget options. That $40 dress from Zara might not last five years, but if I only wear it a few times to weekend events, who cares? The cost per wear is still reasonable, and I’m not expecting it to be a wardrobe workhorse.

The hardest category to navigate is what I think of as “medium stakes” pieces – things like everyday blouses, casual pants, weekend bags. Important enough that you want them to look good and last reasonably long, but not critical enough to justify splurging. These are where I’ve made my most inconsistent choices, sometimes getting great value from cheaper options and sometimes regretting not spending a bit more for better quality.

I’ve also started paying attention to the actual construction and materials, not just the price tag or brand name. My mom taught me to check seams and fabric composition when I was shopping for my first professional clothes, advice I promptly ignored for years before realizing she was absolutely right. A $50 blouse with French seams and quality buttons might be a better buy than a $150 one with sloppy finishing and cheap hardware.

There’s also the psychological factor, which is harder to quantify but totally real. Some expensive pieces make me feel more confident, more put-together, more like the professional I want to be. That confidence might be worth the extra cost, even if the material difference isn’t dramatic. On the other hand, there’s something deeply satisfying about getting compliments on a piece that cost almost nothing, like you’ve somehow beaten the system.

What I’ve learned is that my wardrobe works best as a mix – some carefully chosen investment pieces that form the foundation, some mid-range items that handle daily wear without breaking the budget, and some cheaper pieces that add variety or serve specific short-term needs. The key is being intentional about which category each purchase falls into, rather than just buying impulsively and hoping for the best.

The worst purchases I’ve made have been impulsive ones, regardless of price point. The $200 jacket I bought because it was on sale but didn’t really fit my lifestyle. The $15 dress that seemed like such a bargain until I realized it made me look like I was wearing a potato sack. The $300 handbag that was gorgeous but completely impractical for my actual daily needs.

These days, when I’m facing a price decision, I try to ask myself: What job do I need this item to do? How often will I realistically wear it? What level of quality and durability do I actually need? And honestly – will I still want to wear this in two years, or am I just caught up in the moment?

Sometimes the answers point toward spending more for better quality. Sometimes they suggest the budget option is perfectly adequate. And sometimes they reveal that I don’t actually need the item at all, regardless of price – which, let’s be honest, is probably the best financial decision of all, even if it’s the least fun one.

The reality is that building a professional wardrobe is expensive no matter how you approach it, and there’s no perfect formula that works for everyone. What matters most is being thoughtful about your choices, understanding what you’re actually paying for, and accepting that you’ll probably make some mistakes along the way. I certainly have – my closet is full of evidence of both my good and questionable judgment. But that’s okay. Every expensive mistake has taught me something about what I actually value and need, and every unexpectedly great budget find has reminded me not to dismiss something just because it doesn’t cost a fortune.

At the end of the day, the best piece in your wardrobe is the one you reach for again and again, regardless of what you paid for it. Everything else is just taking up space – and in a Boston apartment, that space is almost as valuable as whatever’s hanging in it.