Let Go of the Label
If you've ever watched a fashion show before, you'd have seen that fashion labels try to promote their wares as entire outfits. "Wear our $300 neckties and $3,000 shoes!" is the message. "This is how real men should dress!" That's all just marketing fluff.
Wearing labeled duds from head to toe isn't a very wise move, and not just because it's expensive. What you'd be wearing then is the style and aesthetic of the designer, window stylist or whoever put the outfit together. Even if you do end up looking good, it'll be under the definition of someone else. You have to ignore what the ads tell you and let go of the notion that 100% labeled is 100% sharp.
Low + High = Stylish
Don't underestimate how much you could get from so-called 'low-end' items. Their material and construction might be marginally lower than name brands, but they're just as versatile as anything that a couturier might be able to offer.
There's no rule against throwing high- and low-end stuff together. In fact, you even have better chances of a more diverse look when you do that. Men's fashion is full of classic examples. Cheap and colorful neckties are vibrant against bespoke silk shirts. $5 army surplus belts add attitude to $300 premium jeans. A Hanes crew neck tee gives contrast to a handcrafted leather jacket. The list goes on.
Invest in the classic pieces that you expect to use for at least a few years. Tailored shirts, premium leather shoes and suit jackets all deserve at least $100 of your clothing budget. Meanwhile, you don't have to spend as much for things like neckties (of which you wear a different one every day) and solid tees (which are indistinguishable from each other).
Cost-wise, this style strategy can make a huge difference. A 3-pack of mass-market tees can cost as little as $10, while designer prices start at $75 apiece. Multiply that across your whole wardrobe and you'll see that it can add up to quite a lot. Investing in fashion involves more than simply buying clothes. You also have to spend a reasonable amount for each one of your purchases.
Love Your Tailor
Back in the old days, fashion-conscious men placed a very high value on skilled tailors. Those guys knew that an expert craftsman could make them look good, even if they happened to be wearing a glen plaid poncho with a neon necktie.