Totally agree with the comment above.
Also, you don't need to spend an absolute fortune on high end clothes.
It depends where you live but stores I love are:
- Jack & Jones
- River Island
- H&M
- Marshalls & TJ Maxx (they have a ton of crap but I walk by a Marshalls every day on my way to work and always stop in for a quick lap, if you are on the ball when new stock comes in you'll get great bargains)
The above have a lot of crap too. But they all sell the staples at very low cost in terms of price vs. quality. They also mainly sell very well fitted clothes.
I've found the first two are awesome for shirts and cool tops and love J&J jeans. Their t-shirts tend to be worn by every guy in town though.
H&M sell all the staples and quality is good. I bought 2 blazers recently $40 each. They are great quality and are fitted. I could go elsewhere and spend $300 for the same and they are just baggy and ill-fitting off the rack.
The best part about being in the US now is that these stores have a very European style meaning the clothes are simple, can mix and match easily to create new outfits every time, and are slim and fitted.
Most guys in my area HATE this but girls respond very well. US sizes and brands go for the "big and tall"... I've bought size small shirts which are like tents on me and I'm over 6ft!
I'm just taking Boston as my example but guys just wear everything huge and baggy, always wear t-shirts and sports jerseys even to fairly classy places so just a crisp white fitted shirt makes you stand out by MILES.
Check eBay too... you can get awesome deals on shirts and shoes on there. Quality caries but you can get some awesome shoes for $30... they absolutely look the part but might not last forever but who cares, just buy a new pair in 6 months. Even $200 shoes from the big stores don't stay crisp with a lot of wear. Best part about this is that you can get styles which nobody else has. I've been complimented on a few shirts/t's I've bought on there because they were so unique.
Main thing is just make your own style and rock it.
There's often fashion trends I see and I like but just don't fit my body shape or my look. I'm very fair haired and I make this work for me a lot. Very outrageous or rocker styles just don't look good on me as cool as some guys can rock it.