Yeah, I didn’t have many clothes at the beginning of my blog, or more accurately many clothes that I liked because having enough to not repeat in a week is a privilege. I don’t “update” my wardrobe on a regular basis, unless I’m saving for something—that’s when adding to my closet is planned and I watch all my expenses for awhile. So for me there’s no formula about how often you should shop, especially since I’m not really one for trends and most of the pieces I buy could have been bought in other years (they’re the same silhouette, sometimes people can’t tell if it’s vintage or new). There’s no need to update (this word implies for me to change and/or keep relevant) your wardrobe if you have a set style, but you can always add when you find pieces that you really like.
Focus first on figuring out what you like. Not just dresses or even vintage dresses, but is it a particular shape you always like, or is it patterned pieces, or are you drawn to some color palette. Whatever “it” is figuring out what you like and want to wear all the time means you’ll buy pieces you want to wear for many years rather than feel like you need to discard after a season. Also shop sales, like buying winter accessories off season and pay attention to fit—don’t buy something that doesn’t fit you because it is a good deal and it’s cute (unless you know a cheap tailor or can sew yourself) because those are the pieces you will not wear. I’m a combination “really need these things” and “spontaneous” but it’s dependent upon price and how high my expenses are that month if I’ll be spontaneous.
I started building my style in college and was using just my part-time cashiering income which was also split with other expenses like school books. I shopped mostly at thrift shops and would try to score good vintage deals online at eBay or Etsy. I couldn’t really even “save” to afford something that cost more because I wasn’t earning enough, but I still wear vintage dresses I bought back then for $8. I didn’t shop all of the time; I realized my budget and set aside a certain amount that was for clothes and could spend that much each month if I found things worth buying. I think if you really want to actively change your wardrobe that is a good way to approach it—have a specific amount each month you can spend on clothes. You don’t have to spend it right away or even use it to the limit each month, but to know your parameters and then to have flexibility within it to make spontaneous purchases that fit the budget or to save for something bigger.
Height is only one factor of body type, so I think it’s about figuring out your shape in addition to your height. I do think if you’re petite then in general loose fitting/oversized pieces will not suit you—they tend to make you look shorter and if you’re curvy then short and frumpy. Since it’s hard to get fit right tailoring helps a lot (but of course that can get expensive), you can also try to buy mostly junior sizes since those are cut shorter. I also think things that hit the narrowest part of your waist help, so jackets that hit there too (try shrunken fits by buying kids sizes) help.
For my body type personally—I like wearing more fitted tops with fuller skirts and skirts that hit at the knee or above. I almost always wear something that defines my natural waist, which will make legs look longer than wearing a skirt lower/low rise jeans/etc.