Makeover: Advice for a (sartorial) virgin?

Hi, I'm glad to have found you guys. I hope you can help me.

I'm in my late 30s. I've never been a really stylish guy, but recent events in my life have pushed me towards getting more sartorially-inclined. I'm still not 100% committed though!
I've worked in casual environments since graduating college, mainly in technology, so I haven't had to devote too much thought to my appearance. I've also been aided by looking younger than my age and being in good shape.

So a handful of chinos, jeans and button-down shirts did fine for work and more formal situations. In casual situations, I most wore something from my vast collection of race shirts from marathons, triathlons, swim races, etc.

But now, instead of working from home, I've had to start going into the office two or three times a week. I'd like to dress a little more stylishly, as I'm getting older, and I'd like to be considered with a regard closer to my actual age. I don't need or want to come in wearing a three-piece suit however. I'm in tech, and that would be considered overly stuffy. I think I can look a little more serious than the hoodie and novelty t-shirt set though.

A few more details about me:

Even though I'd like to look good, I'd like to do so with as few purchases as possible. I just don't like having lots of stuff. I'm not against spending top dollar for something that'll last. Such items have the added benefit of allowing me to go to the store less often. To give you an idea of my mindset, I buy my socks in all black and my underwear in bulk.

I'm also very into low maintenance. If clothes didn't matter professionally or socially, I'd probably be ok with a closet full of t-shirts, jeans and fleeces. As it is, I've fallen in love with no-iron shirts and pants.

I live in the NYC area, but commute by bike a lot too, so low maintenance is good for that as well. I tend to be active and hard on my clothes. I'll often choose to walk rather than take a taxi or a train, probably not the best idea for fine clothing.

I'm small. 5'4", I have a small waist, short legs and thick thighs. I wear 29x29 or 29x30, and lately I've found boy's jeans do me ok. I have a long torso though, so I wear 14 1/2 - 32 shirts.

I used to wear a lot of Eddie Bauer, due to their easy returns, but one of the greatest signs of my growing attention to clothes was to stop wearing their jeans. Their smallest size is 30x30, which often gave me a dad jean look with frayed cuffs. Now I wear tiny 501s and 514s … I tried a 511, and it fit my thick thighs like sausage casings!

I've been exploring using a personal stylist at a place like Nordstrom -- but am leaning against it. Men's fashion seems very similar in all the stores I visited, so I thought it would be better to teach myself than have a person pull things off the rack for me.

I've read these threads so far to get an idea of what I'm getting into -- and thank you all for the intelligent discussion:
http://www.styleforum.net/t/350325/where-to-start
http://www.styleforum.net/a/how-should-i-start-my-business-wardrobe
http://www.styleforum.net/t/343516/need-help-starting-out
http://www.styleforum.net/t/312363/mistakes-you-made-when-updating-your-wardrobe
http://www.styleforum.net/t/309783/if-you-do-not-own-the-following-things-you-are-not-well-dressed
http://www.styleforum.net/t/114678/fit
http://www.styleforum.net/t/343516/need-help-starting-out

I've been making my way through Details' Men's Style Manual, the AskMen.com Style Bible and Roetzel's Gentleman too.

I've also listed the remnants of what I consider my personal collection at the bottom of this missive.

What I'd like to know is:

* What steps should I take to look good at least twice a week? Where should I look? Right now, I'm thinking picking up a blazer or two with decent shirts might help. I like the idea of twice-a-week. It makes dressing more of an event, to impress colleagues, than an obligation.

Also, I can resort to my old stylings the rest of the week, and take my time. (Since one of the lessons from all the threads I've read is to start slowly.)
Priorities for fall and winter should probably come first. I also gleaned from the threads that a pair of casual loafers might be a good idea to add to my shoe collection -- but that can wait until the warm weather returns. I've generally made do all year with trail runners, to give you an idea of my fashion sense.

* Do you recommend a personal stylist?

I'm going to seek out a friend who swears by the shirts he gets from a personal tailor. But I'm a little worried about changing sizes. I can go from 135 lbs to 150 lbs, and get bigger or thinner depending if I'm lifting, swimming or running a lot.

* Any suggestions on how to approach getting fitted shirts?

I hope to be participating more. Thanks for all your help!



Notable clothing for the winter:
One blue wool claiborne suit (dates to mid-90s when I graduated from college, but it still fits! I hardly ever use it.)
One good, thick casual brown belt, one army-style canvas belt, two black belts, one thin and casual, the other formal.
A half-dozen no-iron button-down shirts in various prints.
A pair of 501s and a pair of 511s
Two pairs of cargo pants
Two pairs of khakis
A pair of Bostonian cap-toe shoes
A pair of brown Kenneth Cole square-toe shoes (good quality, but also about 5 years old)
A pair of chunky black slip-on Doc Marten oxfords
One fuzzy old orange wool sweater
One blue, collared merino wool sweater
Two giant J. Crew rolled-neck wool sweaters

I have a huge collection of cotton race shirts, long-sleeve and short and technical clothing for training that's probably twice the size of anything not sport-related.

Great that you went through and read the threads

To start:

There's nothing wrong with a dress shirt/chino or trouser combo. Simple and understated. No need for a blazer if you think it will make you stand out.

No to personal stylist. The forum is free and we will offer better, more insightful advice than any salesperson at any department store.

Which tailor is your friend recommending?

Quote: They say the last time someone got laid wearing cargo pants was back in 'Nam . Joking aside.. you probably want to replace these with some chinos. Check Epaulet/Howard Yount.

Anyways, think of buying clothing and shoes from an investment standpoint. Don't buy cheap stuff just to wear it a few times and throw it out later!

If you've read some threads then don't worry about being a virgin. You (and your wallet) are already fucked.

Chuck the square-toed shoes. Up your shoe game. Get a nice stylish blue jacket or blazer. Nice shoes and jacket are 90% of looking good.

Too long to read, précis it.

Personal stylist to recommend? Not exactly Not associated with any store, just to let everyone know.

Obviously the square-toed shoes need to go. Probably the Doc Martens, too. It seldom makes sense to own more than one pair of cargo pants, unless they are actually used for outdoor physical activities. Pictures of the other items being worn would help determine whether they are worth keeping.