Developing the Rules of the Game

In wardrobing myself, I have a lot of things to think about:
1. My age
2. My size
3. My figure type
4. My lifestyle
5. Our climate
6. My budget
7. My tastes

In considering my age, at 48 years old, there are definitely styles out there, which are too "young". And sadly, as much as I could let my imagination run away with me, and completely make-myself-over into a 1940's Hollywood starlet, I have to accept that the only ones who can really get away with that are urban twenty-somethings. This is where fashions described with terms like: "interpretation" and "influenced by" can come in. And frankly, that takes more work, more judgment. I can't rely on a direct-copy approach, like I'm creating a costume. I must carefully decide which elements of the era are the ones which hold the greatest appeal, and work those into the here and now. For instance, I like the sweet, feminine shapes of the 1940's, but I don't have the tiny waistline that makes everything from that era look its best. Every blouse, every "jumper" (sweater), nipped in at the waist. With separates, every top was tucked into the bottom, revealing the slimness of the waistline, and most dresses were tailored in at the waist, and often, belted. I can borrow the necklines and sleeve and collar details, but I am more likely to put them on tops which are long, almost tunic-length, so as not to emphasize my large mid-section. No belts or tucking in at the waistband for me. I can borrow color palettes, even repro prints. I have a large bosom, and so high, small collars (of which we see a lot of in the 1950's) don't work for me. I do best to borrow from the 1920's and 1930's when you saw more deep vees and scooped or square necklines. Part of what I like so much about dressing in 1st half of the 20th century, was the femininity of the lingerie and accessories. To be sure, it was certainly more fussy, but I have to admit, there are things I like about taking that kind of care, and I do like to be ladylike. The careful choice of foundation undergarments, pretty lacy slips, embroidered handkerchiefs. As a very young child in the late 1960's, I had a blue linen lined Easter coat, matched to my dress. I wore it with little white gloves and a white straw hat with a blue ribbon. I had little white nylon ankle socks and black patent-leather Mary Janes. So prim!
Considering my size now, once again, I find myself betwixt-and-between. I am taller-than-average, but shorter-than-tall. Much of my height is in my torso, and not so much in the length of my arms and legs. Much of my "Plus-size"d-ness resides in my bosom and torso, and not so much in my hips. I am an "apple" and not a "pear". I could be wrong, but it seems to me that the majority of plus-sized ladies are pears and carry their excess in the hips and thighs, and I definitely find this to be how most plus-sized clothing is proportioned.
Which brings me to my figure-type. When looking at pattern recommendations, I am definitely the inverted triangle. I look best in roomy tops and trim, lean bottoms. A dolman sleeve top, covering the waist and high-hip area, and a pencil skirt, will show off my legs, and cover the upper bulk. I look best with darker colors on top and paler/brighter on the bottom, to visually balance my proportions. I can use large prints to break up the large expanse on top visually.
This presents a little challenge for my complexion as I am very fair in coloring and look best in pastels. And so, I do best to have pastel details around the neckline of a dark fabric. Like a layered collar, or a scarf tied at the neck. I look best with a long line down the middle, like a rectangular scarf, tied once low on my upper chest, mimicking the shape of a deep vee-neck. Likewise, if I wear a pendant necklace, it should be rather bold and on a long, bold chain.
My lifestyle: I work full-time in an office with mostly guys (engineering-types), and with minimal contact with the public, so I don't have an external expectation of dressing attractively. But I've worked there long enough to realize that I need to dress nicely for myself, and that it cheers me up in my lonely little cubicle. In my free time, I try to dress for church on Sundays (although there is a wide range of acceptable dress there). Most of my other public appearances are in the grocery store and going to hockey games (just try expressing your fashion aesthetic in the bleachers of a cold, dark smelly hockey rink!), from November to sometime in March, and baseball and lacrosse games in the Springtime, football games in the Fall. Now mind you, I use the term "Springtime" loosely. Here in Maine, we have had to delay Little League Opening Day, because there was still a foot of snow on the ballfield. Most years, the kids have had their pre-season practices on paved parking-lot surfaces, because the fields were either still under snow, or the recently-melted snow had left mud not yet dried. Even if the fields are bare, the temperatures often require sweaters and/or jackets until well into June. I admit to a rather barren cultural life. While raising children, my husband and I have rarely gone out to dinner or concerts, or theater. And children, or no children, we rarely go to the movies, as my husband is freakishly tall, and can hardly sit in most movie-theater seats -- no place to put his knees! So, considering climate concerns, I usually have to dress warm! And during the transitions of Spring and Fall, here in Maine, we dress more like Winter. So I need sweaters, and I wear layers and turtlenecks and tights and boots....
In this economy, need I really comment on the budgetary constraints on my wardrobe? I don't mind too much really, because I have never been one who is interested in having the latest fashions, I never buy any expensive designs, and even if I were inclined to, it would be a huge challenge to find things in my size! Also, part of my admiration for the 1940's is an interest in the impact of WWII and how people had to ration and do without. (Maybe that's why they had such slim waistlines!) I like the idea of being frugal; it just seems to be more responsible not to be wasteful with the blessings we have been given.
And finally, my tastes, I like "classics", and feminine frills, good fabrics, silk scarves and pearl necklaces. I like hand-knit sweaters, crocheted edging and lavender cologne. I try to stand with good posture and walk gracefully. I like an outfit to be well-coordinated, and suited to the activity.
So, given allllll the above considerations, I have my work cut out for me. What about you? How do you deal with the problem of clothing yourself?