I have a firm handle on my casual style, which is sort of a minimalist "grown-up punk/skater" look - t-shirt, dry selvage jeans cuffed up, and Chuck Taylors or Doc Martens, with a thermal, track jacket, hoodie, or Carhartt jacket added as the season demands. I guess the "grown-up" part means that everything fits well now. My jeans are by far the most (only) expensive items of casual clothing I own ... most everything else is secondhand or naturally inexpensive. I'm now a lawyer, and to date I've dressed in conservative, traditional business clothing, as my two legal jobs have been a) clerking for a judge and b) an associate position in an insurance defense firm. My business clothing is mostly Lands' End (shirts, suits, slacks, ties) or secondhand Brooks Brothers (coats). I dress in what I guess is an Ivy League style - sack or minimally-fitted coats, flat-front slacks with cuffs, captoes or loafers, oxford button-down shirts, regimental ties. I think I gravitated towards this style of business clothing for two reasons. First, I don't really have to think about it. It's always appropriate, if not necessarily eye-catching. Second, as I've found myself in conservative workplaces, this style has perhaps compensated for some of my other personal traits that might be considered eccentric in these surroundings. After a short time in the insurance defense bar, it's become evident that neither the culture nor the work itself are for me, and I am taking a significant pay cut to move to the public defender's office. Without getting into a discussion of why I feel this move is in keeping with my personal values and goals, the bottom line is that I'll be afforded more freedom to dress the way I want to - this particular public defender's office, like many others, is significantly more tolerant of individual idiosyncrasies than are the local defense firms. I don't want to take advantage of this leeway to dress like a clown or anything of the sort. I'd still like to dress professionally and appropriately. However, in this setting I'll be more comfortable dressing in a manner other than "American traditional" without feeling like the odd man out. Specifically, I'd like to move to a more fitted, "skinnier" look. Nothing extreme. I'd still like to stay on the "conservative" end of the spectrum, just more tailored - I don't want to freak the normals, I just want to look sharp. Not "mod," but leaning that way - I like Ben Sherman and Fred Perry, for instance. I like a lot of the English bespoke-style clothing I've seen, but there is simply no way I'll ever be spending that kind of money on clothing. Especially on an assistant public defender's salary. I will, therefore, be scouring eBay and thrift stores. My clothing focus is, almost invariably, on value for money. I get a huge kick out of looking good on very little money. I jam econo. My one pair of Nudies excepted. Once I have the basics down, I know I'll be able to fend for myself. However, I don't yet know the first thing about this sort of style, so I'm looking for the absolute beginner-level course in dressing this way - what kinds and cuts of coats and pants I should be looking for, what kinds of shirts and ties, what kinds of shoes go well with this kind of look, and so on. If there are any print or online resources for dressing this way, I'd love to hear about them. I'm 35 years old but am generally mistaken for mid-to-late 20s. I'm about 5'9" and 145 lbs. I wear a 38R chest and a 30 or 31 waist. My hair is currently clipped down with the #4 guide on the clippers, as I've been skating in a park that requires helmets. I don't wear thin solid-color shirts unless I wear a jacket over them, as I have tattoos on my arms and I don't ever let them show in a professional setting. All of my ear piercings have long been retired. I wear basic wire-framed glasses sometimes, although I suspect I'll soon succumb to the siren song of a pair of D&G black-framed glasses, despite the hipster baggage. In short, when I'm in business clothing, I generally look like a reasonably clean-cut, well-put-together young man and would like to keep it that way, I'm just looking to make a slight stylistic shift in my business wardrobe. As always, thanks so much for your help!