:::If your dressing for someone else, you'll always be rotating clothes and feeling frumpy. Find things you feel truly, classically, BEAUTIFUL in. Pair them in ways that delight your senses.
Look in magazines for things you like. Look around you at people walking on the street. Ask yourself, "what IS it I like about that person's outfit. Is it the color? The fabric (the way it flows/is stiff/looks warm)? How would those cuts look on MY body? Are those clothes going to last a decade? Two?"
Look in nature, look in urban landscapes, find visual inspiration.
Fashion, to me, isn't about following trends as much as presenting oneself with beauty and care.
I have a buddy who's fashion is absolutely opposite to me. She's all about loud colors, contrasting prints, polyester, flash, pop, bang. She looks gorgeous...because she wears what feels GOOD to HER.:::
I have a pair of skinny jeans. I'll wear 'em with loose cream colored sweaters and knee high leather boots (I'm in the North West where that is possible 10 months of the year).
Here's my philosophy. I will spend a pretty penny on one good pair of shoes. Once every few years, I'll throw down two hundred on a pair of boots that are dreeeeeamy and GOOD quality. In my climate, these are my every day boots, save 60 days out of the year. They MUST be comfortable and durable to hold up with that amount of wear. I just bought my pair for the next few years after retiring my old ones. They are so tasty. Gorgeous pthalo-blue fluevogs. Yum.
I'll search sale racks until I'm blue in the face and wait until I find the PERFECT pair (most of them start out at three to five hundred dollars so I'll wait and wait and wait until the right ones start getting marked down (and are my size - I have big troll feet)). Once a year, or so, I'll get a nice quality, sale pair of heels/fun shoes/sandals (cost: five to thirty dollars).
I also covet nice quality accessories. My girlfriend, who used to work in an upscale boutique gave me a gorgeous silk/wool blend scarf that is woven with chocolate-grey and honey-cream stripes. I have a pair of nice sunnies from Ross. They are a decent brand, and cost all of seven dollars. My Mom (who is transitioning into her 60s) passed on a nice black leather belt. I've found a few AMAZING finds in little thrift stores in rural america. Things of immense value and quality for a dollar or two. I go treasure hunting. "Will this be something I will still be able to wear in five years?" "How 'bout twenty?" Garage sales and thrift stores have some fantastic finds.
My Mom's wardrobe still includes clothes she bought when she lived in Sweden THIRTY years ago. They are gorgeous and back "in". Heck, she passed some of those on to me when I was a teen, and I still wear them ;-)
Anywho, anything but shoes, I won't spend more than ten dollars on.
But I'll look at magazines for inspiration. I sew and alter some clothes to make them more special (and to fix them when they are wearing down).
Trouser pants are the best cut on me. A slight bootcut jean. I have a few tight skirts, ranging in length. I'll get tights and leggings at Ross for cheap. Those are things that can be switched in and out depending on what era we are in.
I DON'T buy on trend. I love, love, love aesthetics and of course what I like is influenced by what I see around me. I don't get things that are just a fad though. I get things that will last, and that I LIKE and like to pair with other things.
I like buying for fabric. Linens, good quality cotton, silk, wool, cashmere...fabrics are timeless too. I have a slip from the 1940s hanging on my wall. It's tattered, so I don't wear it...but oh is lovely and soft.
Go through your closet and find all the clothes you don't wear. Organize a clothing swap with your girlfriends and dump all the mishaps in a pile..."one person's trash is another's treasure..."