Look, I get it. I’ve spent way too much money on hyped streetwear over the years, camping out for Supreme drops and paying resale prices that make my girlfriend Emma question my life choices. My closet is basically a museum of expensive hoodies I’m too scared to wear because they’re “limited edition.” But here’s what I’ve figured out after blowing thousands on clothes that mostly just hang there looking expensive – sometimes the smallest changes make the biggest difference.
I mean, don’t get me wrong. I still love beautiful, well-made stuff. My saved Instagram posts are full of $300 Japanese denim and handcrafted sneakers that cost more than my rent. That’s part of the problem, honestly. But you know what’s actually improved how I look on a daily basis? Not the Off-White hoodie I waited in line for three hours to buy. It’s the basic maintenance stuff I ignored for years because it seemed boring.
Had this realization during my broke college years in Portland when I was living off ramen and freelance design work that barely covered my student loan payments. Still wanted to look decent at networking events where everyone else seemed to have unlimited clothing budgets, but I couldn’t afford to completely rebuild my wardrobe. Had to get creative about making my existing stuff look intentional instead of like I’d grabbed whatever was clean off my bedroom floor.
Those lessons stuck with me even after my income got more stable. Some of the best-dressed people I know aren’t necessarily wearing the most expensive pieces – they just take better care of what they have. It’s like the difference between someone who details their car regularly versus someone who drives a luxury car but never washes it. Maintenance matters more than price tags.
So here’s what actually works – the under-$50 upgrades that’ll make everything you already own look exponentially better.
First thing that completely changed my game: proper garment care tools. Sounds boring as hell, I know, but stick with me here. For about thirty-five bucks total, you can get a decent fabric shaver and a handheld steamer. These two things alone will make even cheap clothes look twice as good. That $40 Uniqlo hoodie? Looks like it cost twice as much when you remove the pilling and steam out the wrinkles.
I still remember wearing this random H&M blazer to an industry meetup – nothing special, probably cost me thirty bucks – but I’d spent twenty minutes de-pilling it and steaming it until it looked crisp. Had multiple people ask where I got it, assuming it was some boutique brand they hadn’t heard of. The blazer itself was whatever, but it looked intentional instead of wrinkled and cheap.
My steamer is honestly one of my most-used purchases. Keep a travel version in my bag because nothing kills an outfit faster than looking like you slept in your clothes. Even my expensive stuff looks like trash if it’s wrinkled. A twenty-dollar shirt that’s properly steamed will always look better than a two-hundred-dollar shirt that’s rumpled.
Next upgrade that seems stupid but works: shoelaces. Yeah, seriously. For like five to eight bucks, you can replace the boring laces that came with your shoes with ones that actually add some visual interest. Leather shoes look completely different with waxed cotton laces. White sneakers look fresh again with bright white replacement laces once the originals get dingy and gray.
Learned this from this old dude who ran a shoe repair shop near campus. Guys would come in wanting to replace perfectly good shoes that just looked tired, and he’d always tell them to change the laces first. “You’d be surprised,” he’d say, and he was right. I’ve saved so many pairs of shoes this way instead of just buying new ones.
Speaking of shoes – shoe care products are probably the highest return on investment you can make. Basic kit with polish, brushes, and conditioner costs maybe forty bucks and lasts forever. The difference between beat-up shoes and maintained ones is immediately obvious, even to people who don’t know anything about style. There’s a reason people judge you by your shoes – they notice them whether they realize it or not.
My friend Jake works in sales and swears his shoe care routine generates more positive comments than anything else he wears. “People can’t necessarily identify why you look put together,” he told me, “but they can definitely tell when you don’t.” Makes sense when you think about it.
Here’s something I never considered until recently: replacement buttons. For ten to fifteen bucks, you can buy better buttons – horn, mother of pearl, metal – that make ordinary jackets look way more expensive. Even cheap blazers look substantially better with decent buttons. Usually costs about twenty or thirty bucks to have them sewn on, so you’re still under our fifty-dollar limit.
Did this with a navy J.Crew Factory blazer a couple years ago. Swapped the plastic buttons for brown horn ones I found at this fabric store downtown. The difference was so dramatic that people asked if I’d bought a new jacket. Looked like it came from some boutique instead of a mall store.
Let’s talk about the foundation nobody sees but everyone feels: proper underwear. For around forty bucks, you can upgrade from whatever stretched-out stuff you’ve been wearing since high school to supportive, comfortable basics that actually fit properly. Nobody’s gonna see them (well, hopefully someone will eventually), but they affect how everything else drapes and how confident you feel.
I was buying whatever was on sale at Target for years until Emma basically staged an intervention about my sad boxers situation. Finally invested in decent undershirts and boxers, and the difference was immediate. Clothes lay better, felt more comfortable all day, no weird bunching or riding up. Sounds minor but it’s one of those changes you notice constantly.
Quality no-show socks might be the most underrated upgrade ever. For twelve to fifteen bucks per pair, these solve the eternal problem of wearing loafers or low-profile sneakers without looking like you’ve got bare feet. The cheap ones constantly slip off your heel or bunch up weird. The good ones – with silicone grips and proper construction – stay put all day.
I suffered through summers with either visible athletic socks (which looks terrible) or no socks at all (hello, blisters and foot odor) before I found ones that actually worked. Game changer for casual outfits. Suddenly everything looked more intentional instead of like I’d just thrown stuff on.
For dress shirts: collar stays. Pack of metal ones runs about fifteen to twenty bucks and keeps your collar points from curling throughout the day. It’s subtle but separates guys who look sharp all day from those who progressively fall apart. I keep sets everywhere – desk drawer, car, travel bag – because there’s nothing worse than realizing your collar looks like garbage right before an important meeting.
This might sound weird, but a clothing brush has been huge for me. About twenty to thirty bucks for a proper one with natural bristles. Lets you remove dust, lint, and light stains without washing or dry cleaning everything constantly. Extends the life of your clothes and keeps them looking fresh between cleanings.
Watched this old tailor brush down a customer’s jacket after a fitting once, and when I asked why, he looked at me like I was insane. “Of course you brush your clothes,” he said. “How else do they stay beautiful?” Ordered one the next day and use it religiously now. Few habits have done more to keep my stuff looking good long-term.
If you wear dress shirts regularly, collar and cuff cleaning solution is like ten or twelve bucks and dramatically extends shirt life. These areas show dirt first, but targeted treatment keeps them looking fresh way longer than regular washing. Discovered this after ruining several white shirts with yellowing collars that no amount of normal laundering could fix.
Here’s a controversial take: sometimes the best upgrade is subtractive. Taking an ill-fitting piece to a tailor for simple adjustments – usually fifteen to forty bucks depending on what needs fixing – can transform something that’s been hanging unworn into a favorite. I’ve “discovered” amazing pieces in my own closet after finally getting them properly altered.
My buddy Marcus has built his entire wardrobe from thrift store finds that he then has tailored. “I’d rather have three perfectly-fitting secondhand blazers than one new one that’s just okay off the rack,” he says. Costs less and looks better than what most people achieve shopping retail.
Fabric rollers are unglamorous but essential. Eight to ten bucks. Nothing ruins an outfit faster than visible lint or pet hair (Emma’s cat sheds like it’s his job). Keep one at home, one at work, travel-sized one in my bag. Instant fix for something that many guys just ignore until someone else points it out.
For leather stuff – belts, watch straps, bags – leather conditioner runs about fifteen to twenty bucks and provides amazing restoration power. Dried-out leather ages you instantly, while maintained leather develops this rich patina that looks better over time. Used it on a vintage briefcase I found at a flea market and the transformation was so dramatic it looked like a completely different piece.
Most overlooked upgrade: proper hangers. For around forty bucks, you can replace the mismatched wire and flimsy plastic hangers with wooden or substantial ones that maintain your clothes’ shape. I replaced mine gradually over time, and the difference is remarkable. Clothes keep their shape better, closet looks organized, everything seems more intentional.
Saved the most impactful for last: basic sewing kit and knowing how to use it. Total investment maybe fifteen to twenty bucks. Being able to reattach a button or fix a small tear puts you ahead of like 90% of guys who would either live with the problem or throw the piece away. My kit has saved countless items that would otherwise be toast.
Learning basic sewing was my resolution a few years back. Nothing complex – just enough to handle small repairs. That fifteen-dollar investment has saved me hundreds, maybe thousands in replacement costs. Plus there’s something satisfying about maintaining your own stuff instead of just throwing things away.
None of this is particularly exciting or Instagram-worthy. You won’t get compliments specifically on your collar stays or steaming technique. But together, they create the foundation for looking put-together in a way people definitely notice, even if they can’t pinpoint exactly why.
The truth is, style isn’t just about buying the right things – it’s about taking care of what you have in the right ways. The most impactful upgrades aren’t additions to your wardrobe but improvements to how you treat it. Learning to properly maintain and present what you already own will take you further than most splurge purchases ever could.
Before you drop hundreds on that new jacket or those hyped sneakers, consider whether a strategic fifty-dollar investment might actually do more for your overall appearance. Sometimes the smallest changes create the biggest difference. Took me way too many expensive mistakes to figure that out, but better late than never, right?
Keith’s a Portland designer with a soft spot for sneakers and a growing allergy to hype. He writes about streetwear’s creative side, its excesses, and learning to build real personal style beyond the latest drops.
