Those are some pretty sweet hats. I've been looking into getting something on the fancier side like that, but I haven't really had the courage yet. I just don't know what would look good on my head.

Since graduating from school I've been trying to step my game up. With a thread title such as this, how could I not subscribe?

Minarchist, how did you go about finding your tailor? I hate baggy dress shirts; even some "fitted" shirts aren't that tight.

Here's a shot rocking the Stetson. It was a casual dress for a friend's birthday party outing. Please excuse the crappy low-light cell phone photography in an as-of-yet unrenovated section of our fixer-upper house.

Subscribing for wishing to having dapperness.

I do have a buddies uncle who I go to for tailoring. Get a pretty good friend discount.
Subscribed for dapper as well.

Fixed.

Dressing Dapper is nice. Dressing Dapper on a budget is very, very hard.

My biggest problem is that clothing is hard enough to find in my size (6'2", thin as a rail) that finding items that are my size and on sale is an epic quest filled with lots of grinding (of my teeth). It's all about priorities, and I could certainly have bought more clothing if I bought fewer video games, but it's still a constant source of frustration that I have to special order most of my clothes, anyway.

I'll have to give eBay a closer look. Thanks!

Also, yes, I tend to stick to European heritage. It fits me much, much better.

So there's basically three fits [gross oversimplification alert]. There's the Savile Row (London) fit, which is what you think of when you think investment banker. Short but high shoulders, a lot of waist suppression, larger and very stiff canvassed chest, etc. There's the European or Continental fit, which basically means the Italian fit since they're the only people in Europe who make clothes that anyone else cares about. This is characterized by a few different styles of shoulder, some interesting sleeves, a very clean chest and silhouette. More "slim" for the most part, and the measurements back that up. Compare the actual chest, yoke and waist measurements on a Brioni versus an Oxxford or Brooks Brothers and be amazed! (Not that different clothiers having different sizes is new.) The third fit is the American or "sack" fit, which is basically a box of a suit. There are those who like this but I tend to think it looks pretty terrible. Combine the general shapelessness of the clothes and suits with the fact that most suit salesman try to put you into suits way too big (I once had a man try to sell me a 42R, when I'm a 36R-38S), well, you get the idea. The look is most typically personified by Brooks Brothers, though most of the warehouse-style stores carry the same thing (Joseph A Bank, Men's Warehouse, S&K).

As far as finding the continental stuff...if you're looking for higher-end clothes, try to find discounted Brioni, Zegna, Kiton, and other high-quality Italian names. On the (much, much) cheaper and lower-quality end, H&M is not so bad. Sometimes you can find something pretty close, like Brooks Brothers' "extra slim" fit, though if that's still a bit wide you may want to get the shirts darted, which is I believe free at any BB location. It also gives the shirt a nicer silhouette IMO.

ETA: Here's more about silhouettes than you will probably ever care to know.

You're in Denver, should be easy.

Internet says check out Y&Y, or try Cherry Creek Tailoring (ask for Hamdi, apparently). Erol's also got a shout-out.

If you're looking to get custom made clothes, there're a few adequate places that take your measurements and produce the clothes at a distance. Jantzen is supposed to be good for shirts.

As someone who's wardrobe consists mostly of Columbia cargo pants and polo shirts, where should I should I start on my journey to dapperosity? Please use simple terms, I'm an engineer.

AAAC may be the most cordial place on the internet (even moreso than GWJ!), but follow their advice too much and you'll wind up looking just like an investment banker; they're very Savile Row. Style Forum, though significantly snarkier, is probably a bigger wealth of information and more geared toward a continental and fashion-forward look (also has a lot more college students asking how to start upgrading their wardrobe from threadless tees and sandals, so apropos in your case). Both are useful resources; they serve slightly different needs.

Since I'm sort of in the same place as you, Kraint, just a little farther along in the journey, I'll share what I've done so far:

1. Learn what fits. I mean what really fits and how it's supposed to, not what your typical Joseph A Bank salesman will say "fits" (I highly recommend trolling this, this and this thread). Then, find the sizes that actually fit your body. This will require learning a couple more measurements than just "suit size", like the yoke (back piece between shoulders), chest pit-to-pit, and actual waist size (not pants size). Once you kind of learn what numbers fit your body (this may require spending a lot of time in a department store somewhere), buy it and measure it. Better yet, get it tailored to an even more precise fit then have the tailor measure it. Then...ebay!

2. Learn what good quality actually means. Most famous brands like Calvin Klein or Banana Republic, even up to the ranks of Dolce & Gabbana, make absolutely horrible menswear. Use duct tape to keep your head from exploding with your newfound knowledge.

2. Find cheap resources, like The Tie Bar (mentioned above), ebay, thrift stores, outlet malls, etc.

3. Realize that Rome wasn't built in a day. Start with 1-2 staple suits (charcoal and navy), maybe a light gray sportcoat, a few standard shirts (white and light blue oxford, maybe a pink or purple stripe), a couple well-fitted pairs of slacks (maybe gray and light tan or brown), and a couple conservative ties. You'll see a lot of crazy and cool stuff in the above fit threads, but that's for people with a lot of time and money to go after that sort of thing. Bespoken suits from famous London tailors, >$500 Kiton shirts, etc. are not for us unwashed heathen — unless you get crazy lucky at Goodwill, of course. Under the same principle, I'm sort of gearing up my daily wear. Not going straight from polo-and-jeans to suit-and-tie every day, but working through slacks and shirt/tie, slacks and sportcoat/no tie, etc. Unless you just landed a job in finance, in which case, feel free to go 0-60.

I just found a beautiful super 120's wool Oxxford charcoal pinstripe suit for a whopping $175 at our local men's consignment store. It's a 40s when I'm more like a 37s, so it needs to be taken in fairly substantially everywhere (shoulders, chest, waist, sleeves, pant waist, and we're taking the pleats out of the pants), but my tailor swears she can do it. For reference, these may be the finest suits you can buy (Oxxford, that is), and they typically run $4k-$6k new. The thing feels amazing. It's going to be tough waiting ~two weeks to get it back from the tailor. This place just got in a ton of Oxxfords and Zegnas from some guy who is apparently cleaning out his closet, but most of them are in the $400-$500 range, so I'd have to wait 'til the rest of them got green-tagged before really being able to get around to them. But I'm a patient man...

I also snagged a somewhat meh Brooks Brothers navy chalkstripe for $80, so I guess that's good.