Dear 100 Hour Board,
How do you learn how to dress well on a budget? I like the clothing from Loft and AnnTaylor and Anthropologie but I can only afford to shop at thrift stores. How do I make my clothing look like outfits and/or work with what I have? Can one of you help style me? Haha! But really how are some girls so effortlessly stylish and look like they are wearing outfits but when I wear clothes it doesn’t look like an outfit. It just looks like clothes!
-help me dress myself
I think the most important thing is to be discerning about what clothes you allow in your closet. Only own things that are in decent repair, fit you well, and serve a definitive purpose. No one is doing it effortlessly. But it almost feels effortless when you have the right clothes in your closet and nothing else.
As with many things in life there is a investment trifecta. Good, cheap, fast style is everyone's dream. Sometimes the stars align and your mom hands you a vintage piece you won't find anywhere else or you walk into a clothing swap and find the perfect thing after 2 minutes. That middle grey space does happen but it usually comes in strokes of luck. Most of the time you have to spring for the purple, green, or orange space. I would not recommend shooting for the green space in any aspect of life that is important to you. That is reserved for our lowest priorities
If you want to dress well for cheap you are going to have to sacrifice your time. Take a hard look at those things you love at Ann Taylor and Anthropologie. Figure out why you love it and what functional group they belong to. Then go out into the thrift stores, sale racks, and online clearance pages to find something that does the same thing. Tell yourself it doesn't have to look exactly the same. It just needs to serve the same function and make you happy. It may take months of checking everywhere you go.
You should be scrutinizing and avoid buying things you have significant doubts about. Shopping for function and quality has been a game changer for me. If it doesn't look like it will last, don't buy it. If you will have to alter it in any way (tailoring, cardigans, or t-shirts underneath) don't buy it. Remember that you pay for an item long after you swipe your card. You have to give every item your time, attention, and closet floor space. Get rid of things that are wasting those precious resources and distracting you from the items you love. Also, take care of your clothes. Dingy clothes are no bueno no matter how cute they used to be.
I have a hard time taking risks but sometimes they just pay off so well. If you're like me then try to pay attention to outfits that work but are unexpected. Remind yourself that you are now officially allowed to do that. After mimicking the risks of others you'll have a better idea of your own taste and you can take your own risks. I mean you can do that anyway, but I noticed my risks started going better after I practiced with others'.
I wrote this answer a few months ago, and hopefully some of my ideas from there will be helpful. Those are my general fashion rules, limited as you are by a meager budget for new clothes.
I can't claim to be an expert on fashion. But I do have one main point of advice that hopefully will help, besides the suggestions I give in the above answer.
Don't go shopping by yourself.
Of course you don't have to drag anyone along with you all the time, but having a second opinion, especially from someone who is familiar with you and your wardrobe, can work wonders. They see the outfits from a different perspective than you do, and they might be better able to assess whether a particular item of clothing is flattering on you. Especially if you shop mainly at thrift stores, you may have limited options, and taking a friend with you can help pin down the best pieces for you in particular.
One other piece of advice is echoed from the answer I reference above, but to turn simple clothes into an outfit, choose a focal point for each outfit you put on. Whether it's a statement necklace or a patterned pair of pants, when balanced out with neutrals, such focal points turn clothes into outfits by adding your own individual taste and style to what you wear.