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Marcus Kirby
by Published on January 14, 2020

Sometimes investing in a trend (regardless of the price tag) gives you a moment of pause because you sit there wondering if everyone will have moved on in a month and this waste of money will still be hanging in your closet. Thanks to social media, the trend cycle moves at lightning speed these days so the chances of said item being over before you even got to wear it are high. After experiencing this situation one too many times, I made it a point to only invest in trends I see some sort of longevity in.

The safest way to ensure the trend has longevity is to buy into the ones that skew on the classic side. A trend that's also classic, sounds weird right? Let me explain: Certain trends may fluctuate in popularity, but never truly go out of style. Think trends like leopard print or skinny jeans—they're timeless trends that will never actually go away. So when you find an item that checks both of these boxes and is affordable, that's a purchase you should feel confident in.

Below, I've found 19 items that check all three boxes. They fall right at the intersection of cheap, trendy, and classic (I even made a handy Venn diagram to illustrate said items, in case you're a visual learner). Keep reading to see and shop all 19. 

Cardigan sweaters are having a resurgence at the moment—they're arguably one of the biggest trends right now. However, they never truly go out of style, so they're a safe investment that you'll wear for years. 

Snakeskin cycles in and out, but it's also one of those prints that's never truly out—maybe just slightly less popular than other seasons. Pointed-toe boots are also always considered cool.

Teddy bear coats are one of those jacket styles that everyone will wear year after year simply because they're cozy. And who wants to give that up when temperatures drop?

Vans Old Skool sneakers are as classic as they get, but they've managed to maintain their cool-factor for decades. This is one pair of sneakers you'll never regret investing in.

Zebra stripes and sequins check the trendy category for sure, but they're also both trends that come back year after year. This guaranteed repetition puts them into the classic territory. 

Chain necklaces are going to be huge this year; they're here to replace the trend of dainty gold layers that's been prominent for so long now. And even though gold links will be hugely popular, it's a style that doesn't read overly trendy or trying too hard.

Puffer jackets have been seen on all the cool kids in recent seasons, but that doesn't change the fact that they're a winter wardrobe staple that everyone should own. A jacket that will actually keep you warm and make you look cool is a win-win in my book. 

Knee-high boots are having another renaissance this winter, but they never truly left. They're the ideal winter boot because of their shaft height, and if you're feeling extra trendy right now, try tucking your straight-leg jeans into them for a very 2020 look. 

You already heard about the gold chain-link necklace, but silver is making a comeback as well. Layer this statement piece with your favorite delicate necklaces for a fun neckline. 

A chunky sweater is as classic as they come, but recently we've seen fashion girls tucking their favorite knits into interesting bottoms like colored leather and coated trousers. 

Classic Levi's will always be considered cool, and this straight-leg style is just a bit more trendy than a skinny jean. 

Leather separates are one of the biggest (if not the biggest) trends right now, but they're not exactly new. Leather shirts have fluctuated in popularity for decades, so if you want to jump in on the trend now, it's safe to say they'll be considered timeless.

Mock croc is the texture that always looks expensive, regardless of the price tag. This color combined with the pointed toe and mock-croc material makes these boots feel directional, but all three of these elements will always be in style.

Blazers have been wildly popular for years now, given the recent suiting trends. But they're an office staple that will always look polished. You can throw one on over jeans and a T-shirt, and you're guaranteed to look chic.

A good bodysuit belongs in everyone's wardrobe, and this one-shoulder style feels super relevant right now.

A cropped cardigan definitely skews on the trendier side, but paired with high-waisted denim and boots is always a good outfit combination.

Oversize totes are going to be huge for 2020, and this one maintains a classic feeling thanks to its camel color and sleek texture. 

Give your skinny jeans a break and try this straight-leg style instead. It looks a bit more effortless, but still completely pulled together. 

If you're into puffer jackets and want to branch out a bit, give a bold colored puffer a try. It still looks timeless, yet adds more interest to your winter outfit. 

Next up: 5 cheap basics that'll actually make your outfit more stylish.

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