Let me answer to one response at a time: Quote: Thank you. I don't go to a gym, but I've started since three months ago lifting weights two or three strenuous sessions a week, and I still go on the occasional hike or walk as well. I'm not sure about gaining twenty more pounds, but I could look good with more muscle. I'm trying to maintain a versatile wardrobe, so thanks. I'm actually going to buy new suit separates slacks for my suit, to complete the tailored fit. I made the mistake of getting the traditional full cut, so I'll see how the new one goes. Quote: I live about an hour away from Los Angeles, so there are certainly a lot of malls and stores around. My total budget isn't defined, but I'm still reluctant to spend more than about 150 for shoes, as an example, or about that price on a sports jacket. I'm at a point in my life where I must make the most of what I have, and I'm unemployed, which does not help the matter. There's some good advice you've posted, but after giving it thought, I never really cared about how overdressed I may have been perceived for the last two years. If anything, I'm just trying to remain consistent with my style, but putting more thought into the fit and quality of my clothes than before. I started with the objective of trying to dress nicer, since four years ago starting in community college, and it's now leading me to the point where I'm trying to refine the foundation I've set out to follow. I guess I could get away with adopting a more casual approach to style and still look good, but I feel obligated to maintain certain dress standards for myself. I'll certainly consider a new pair of jeans (probably Levi 501s in rigid) and good casual shirts. Quote: I get you, they're too wide and they just can't hold a crease (Land's End chinos have been a hit or miss for me, the grey ones I'm wearing above with the navy sweater are better fitting). I wouldn't burn 'em though, they'll just get relegated to being worn for yard work or hikes, sort of like my baggy olive Cabela's are right now. I need a replacement khaki that is in between the fit of this and the very skinny pants popular right now. I want something that isn't skin tight, but isn't so loose like the ones pictured. I'm not sure about low rise, but I can do with an inch below my navel. Quote: Most of my shirts are some kind of button-down collar variety. I should save up for a good point collar (no buttons) white shirt though. Quote: I think you're right about that. From pictures I've seen of European and Asian businessmen, button-downs don't seem to be as common as in the U.S. OK, and now I'll close tonight with another picture of the McGregor Anti-Freeze and jeans (Levi's 505s, I've had them for over two years, and they were originally unwashed/rigid): It's nowhere near as stylish as a red version of the jacket is (like James Dean), but this is one of my most prized parts of the wardrobe, despite just being a frumpy looking brown nylon jacket. It's 40r, fits, and it's comfortable, so I think it's a keeper. As for the jeans, they were in better shape before, but they're starting to get a hole on the right knee. I'll get a replacement eventually, and use this for the great outdoors. The more I'm reading this thread, the more I feel compelled to react as soon as I can to step it up a notch. I would rather be perceived as enjoying and "owning the look" of the type of clothes I usually wear (and I do prefer to dress with business/smart casual sensibilities), and not to be seen as getting ready for a job interview. Most guys going to a job interview I've known of recently wore black suits, so I think my choice of light charcoal does something to distance myself from that stereotype. Black suits don't do it for me anyway, though. Thanks for the suggestions.