Make money doing the work you believe in
Someone recently asked me if I could help them find a pair of white pants, as they have a large wardrobe that doesn’t cohere, and they believe the white pants will allow them to play more with different combinations. They are tired of buying lots of low quality items and would like to shift towards more high-quality items.
This is a very normal and relatable experience. But IMO, the answer to this problem is not to "buy higher quality clothing" or "add a new color." I think building a more fulfilling, coherent wardrobe can be done thusly:
First, decide how you'd like to dress. You may not like your wardrobe because you haven't yet developed a strong sense of taste. You can cultivate this taste by first thinking of clothes as a cultural language shaped by history.
Thus, start collecting photos of outfits that inspire you. Hopefully, this is more than just a collection of trending images from Instagram (which today, all seem to fall into the "cropped shirt, big pants" silhouette). Look beyond fashion images, influencers, and celebrities.
Instead, think about culture. Are you inspired by a 1950s Italian Riviera aesthetic? 1960s Ivy Style? 1970s NYC sleaze? 1980s punk? 1990s skate or hip hop? And so forth.
Alternatively, you can think in terms of menswear archetypes: the worker and soldier; the artist and peacock; the intellectual and academic; the rebel; the outdoorsman; the bohemian; and so forth. Each of these identities has been represented by different aesthetics over time, with each era shaped by the last, so there are some unbroken themes.
You don't have to recreate these looks exactly — it does not have to be cosplay — but by understanding these different aesthetics and their themes, you can use this visual language to express yourself in a way that feels authentic to you and fitting for our time. Just as I'm speaking to you right now using a shared language shaped by history, you can do the same through clothing.
Second, pay attention to your relationship with clothing. What do you wear the most? Which items in your wardrobe make you feel most like yourself? If you find that you mostly wear the MA-1 bomber jacket instead of the tweed jacket you bought with good intentions but never wear, then perhaps you're into workwear. So consider other items that fit that tradition: olive fatigues, blue jeans, mid-century-styled Army chinos, and so forth. Your first-hand experience with clothing, especially tracked over time, will be a good indicator of what might be a good next purchase.
Third, don't think of clothes purely in terms of quality. There are, of course, some basic measures of quality. Knitwear is often better when it's made from long-staple fibers, as those are less likely to pill. Tailored jackets are better when they're canvassed rather than fused. Leather shoes are often better in full-grain leather rather than something too plasticky.
However, clothing is not the same as electronics, where you can max out measurable specs, such as RAM or processing power. Instead, clothing is more like cooking. If a hundred steps go into making a garment, a designer has to decide which matter most to their vision. This is similar to a chef creating a dish. If they want to hit a certain price point, they might use basic olive oil but splurge on premium tomatoes. Another chef might think that olive oil is the most important ingredient, so they reverse those decisions.
The same is true for clothing. One designer might use a very heavy, robust fabric for their jeans because they want the material to age a certain way. Another designer might prioritize lightness and comfort, so they use a lighter material. Different consumers will also prioritize different things, much like how we don't all order the same thing at a restaurant.
Thus, when buying clothing, pay attention to which qualities you prefer and think about "emotional durability." Will you enjoy wearing this thing five or even ten years from now? As much as you enjoyed wearing it on the first day?
These four steps ...
Thinking about clothing as cultural language shaped by history
Collecting cultural images that inspire you, hopefully beyond Instagram influencers, fashion media, and celebrities
Paying attention to which clothes you love most in your wardrobe
Considering design and "emotional durability" when shopping
... will help you out of this problem. You will have a more coherent wardrobe and pieces you love wearing.
Adding random things, focusing only on "physical quality" (a vague dimension), and abstractly playing around with color (t-shirts in blue, green, white, brown; pants in blue, black, and white) will only exacerbate the problem.

