Spending a bit of extra money on something you'll wear all the time for a long time... makes sense.
Blue Jeans
You need a good pair of jeans.
Jeans that you are not only comfortable in, but fit you perfectly.
Blue jeans go with nearly everything, can be dressed up or down depending on your footwear and shirt choices, and you can wear them in almost all weather conditions.
Finding your perfect jeans can take years of searching, but when you find them, you'll know.
But, I've found that almost all of my favorite, favorite, favorite pairs of jeans (i.e. the ones that I will wear at least four or five times before I wash them again) were not what someone would consider "cheap." However, I will say they're nowhere near the cost of "expensive" jeans ($100 range jeans).
I think expecting to spend around $50 for a pair of jeans is a reasonable cost, because, like I said, you wear jeans all the time. You want your jeans to be comfy. You want your jeans to be the right length, the right rise, the right pockets... there are so many things that go into a perfect pair for you.
Do not settle for a pair of jeans because they're affordable. You deserve the perfect pair. And the perfect pair exists.
Black Jeans
After you've found your perfect pair of blue jeans, you should definitely see if they come in other colors and washes, specifically black.
Black jeans are easier to dress up, since they can almost (almost) be mistaken for slacks. Almost.
I personally own the exact same style of jeans that I consider my perfect pair in both a dark blue wash and a black wash, and they were both very worthwhile investments. You already love them in one wash, why not get them in another staple-worthy wardrobe piece?
Black jeans, like regular jeans, are almost a universal bottom that you can wear with nearly every top imaginable and every shoe imaginable.
Universal Lightweight Jacket
I say universal to mean something that, again, you can wear with everything. Personally, I enjoy a good jean jacket, but there are neutral bomber jackets, cargo-style jackets, etc., that will do the trick in a similar way.
It's important to get one that won't fall apart on you, because this will be something that you'll want to wear a lot in the in-between seasons, that is spring and fall, to add a bit of additional warmth when it's just a little chilly but not cold enough for a coat.
Just like buying jeans of a good quality, it's important to buy a denim jacket of a sturdy enough material that you can wear it day after day, season after season.
Cozy Cardigan
Cardigans are easy to throw on over dresses, blouses, T-shirts, button downs, and pretty much anything in general. You can wear them with leggings or jeans, shorts, skirts... they're just another universal piece, so buying one that you truly love and know will last you for several years is important.
You don't want to buy a cute cardigan, wear it every day for a month, both around the house and out in the world, and it's already falling apart at the seams.
My mom has a tan O'Neill cardigan we bought seven or eight years ago, which she wears frequently, that looks practically brand new. It was a good investment cardigan.
White Sneakers
I am a firm believer in the white sneaker (I own seven pairs).
They go with literally everything. They're comfortable. They're casual but still stylish. If they're leather or fake leather, they'll let you walk in the rain or snow. They're such a classic item that they will never go out of style. If you don't know what shoes to wear, white sneakers, nine times out of ten, are a very suitable option.
And there are so many different brands that make unique shoes that come in white, so no matter who you are, you can find a pair of white sneakers that fit your style.
