First; go basic on colors: black; white; brown; and blue. At this point don't worry about what colors flatter you; just get some basics. If/when you finally figure out what colors/shades look good on you; you can always add pieces later to your basics (scarfs; blouses/shirts; etc.)
For women I always recommend New York & Company. They always carry suit basics that are still fashionable but not ever really out of fashion; but do not look or feel too matronly. I have several suit pieces by them and they have held up well (admittedly I do not have many places to wear a suit; however) and I bought them between 6-9 years ago and they still look in fashion.
In pants; long and straight is always workable and almost always in fashion. Don't go for either end of the spectrum: really close to the leg (legging/major-ly tapered) styles; and don't have really hugely large-legged styles either. If you're short or/and pear-shaped; the long and straight makes you look slimmer and taller. If you are already slim and tall; it just streamlines you. Don't go for either high-waisted or low-waisted for obvious reasons(although I have to admit loving the high-waisted mid-thigh skirts that are now in fashion; but they could and probably will fall right back out of fashion soon!).
In jackets; I am tempted to say the same (almost): longer is better than shorter because shorter tends to visually 'cut you off'; and most people don't look good like that. Get something that at least covers the top of your hip area; if not longer.
For casual; again darker and straight-legged jeans are almost never really out of style (except in the 80s; lol!). They are like black - they really go with everything; and can be easily dressed up with a nice top.
Shoes - try not to go to extremes here either. Neither really pointy toes or really rounded/square ones (exception: men's square-toed dress shoes are still really good-looking!!). For women: don't go for major-ly chunky 90's style (think Doc Martins) heels on shoes. Get a nice pair of heels in either a skinny or mid-chunky style in black or brown (whatever your wardrobe calls for in majority color) and a nice pair of calf-to-knee high boots with a mid-chunky heel (not a really skinny one; looks hooker-ish..and this is coming from an exotic entertainer! :) ) The newest style in shoes is the ankle boot (think re-vamped 80s)with a mid-chunky heel. If you like this style or think you can wear it; it's a great alternative to wearing all heels or all boots; and it goes well with both suits (pants) and jeans. If you want to wear it with a skirt you might want to look up some pictures of ppl doing so; I don't have advice for that.
I don't try to challenge the fashion world very much. You will find me out partying in my dark jeans; a cute pair of heels (this is where I splurge personally when I have the money) and a black nice top. I don't take risks with the colors; so therefore I can take some risks with the styles (I will buy a cute top in a newer style). Does that make sense? It's a safe bet to only take a fashion 'risk' with one piece at a time.
I dress my husband in basic black/brown stylish shoes; nice black or dark blue jeans; and a fashionable shirt (he's a dj). He has two suits; fairly well tailored to him in black and white; single-button. We both like double-breasted suits; but it is really easy to go wrong with those and look dated unless they are really tailored to the individual person. He picks out the color shirts he likes and that's how we compromise. He also has great taste in ties :)
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