I Like: -floaty skirts, little vest tops/camis -50s style like crop trousers/jeans to go with with tie no sleeve shirts. -summer heels but not too high and comfy -swing dresses. dresses that i can wear both to work and play. Notes: new york is also sticky and humid so cotton things/denim dresses/thin fabrics (but not silk) are good.
Budget: zero dollars! would spend up to $140 ish on a dress if it was amazing but ideally keep everything under $100/$80 dollars. and cheaper the better.
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So you are now (soon to be) 30 which is officially adult so while you can still keep your cutesy floaty skirts and blouses I think we need to look for a few more grown-up looks. Nothing too extreme but something a little sexier and mature. Still fun, just an updated, sleeker look for you.
Don't shop (for summer clothes) at thrift shops: this is gross. Plus you will need to spend a LOT on getting your items professionally cleaned to ensure no lingering smells/stains, so it's not really worth it. RESIST!
I am assuming you have or can borrow cool acessories - we're going for multi-usage outfits with interchangeable elements. Accessories are you friend here.
I am also assuming that you have several light-weight cardigans to layer with when necessary. At least one should be black. One should also be mid-thigh length if possible, like this.
I don't know how you feel about Old Navy and Victoria's Secret. I personally love both; they make good versatile pieces that last so a lot of the stuff in this post will be from them. You can look for simmilar items at other places you prefer but the reasons I am linking to them are a) cute and seasonal, b) they both carry up-to-date shapes that are a good reflection of what's out there and c) they are at the right price point: currently VS has a really good sale and Old Navy is always great value. I'm also going to be linking to Lauren Conrad's Kohls collection because it's super cute and good value.
Clothes
Dresses
Do not be tempted by any dresses/skirts that are below knee-length! You are short and I'm guessing will be wearing mainly flats so longer lengths will do you no favours! If you want to play with length, try one of those hi-low hem dresses. Personally, I find them a little weird but there are some cute ones!
This style of dress is super cute and you can accessorise it in different ways for work (black cropped cardi and ballet pumps/jewelled sandals) or date night/bar (hot heels and sexy makeup/jewellery) Also take note of her wedge shoes: we will come back to them.
This is also darling and easy to wear day or night:
Going with a simple wear-everyday dress with tiers/ruffles (see below) I have a couple similar to this and they are so useful and obviously you can do whatever you want with them. Comfy, flattering, kinda ballerina styled! Buy a couple of these; they have great cost-per-wear.
This shape fits with your 50's style request and again, so easy to style.
Another 50's (ish) style, sexier but still cute, the teal would be good on you.
Also cute, easy summer dresses here, here, and here
Shirts, Jeans and Shorts
Aside from basic black tank tops and a nice white shirt (goes with everything, versatile etc) below are some fun things to wear with denim.
Something like this is cute with cuffed jeans and flip flops, or super-sexy but still casual for boardwalk/brunch with denim cut-offs and wedges(see above)/jewelled sandals. (you are running all the time so your legs must be tone enough for denim shorts, so long as they are not crazy short)

