16 investment pieces that are worth it in the long term

A classic blazer will never go out of style. And committing to a beautifully cut iteration adds an under-the-radar elegance and "je ne sais quoi" to anyone and any outfit — from white T-shirts and jeans for lunch dates to button-downs for a big job interview. Practically speaking, you could own the same version for decades — so it's worth investing your money the first time around in something you love.

A leather jacket, like most of this list, goes with pretty much everything. It's another piece you can technically buy only once and then own for decades (I personally have one of my mom's leather jackets from the '80s).

Leather itself is also a uniquely good investment; the material is durable, functional, and is one of few that actually gets better with time — molding to your shape to create a custom fit. For this reason, it's alright if your leather jacket is a bit tight in the beginning (but not if it's too loose) — it'll stretch slightly with time.

• This leather jacket is one of my closet's best-kept secrets — I've worn it for 2 years and it's only getting better with time
• Everlane's first leather jacket is a sleek alternative to typical moto styles — it's also surprisingly affordable

The most versatile shoe is neither the sneaker nor the low block heel. It's the walkable bootie, which pairs with work slacks just as easily as your jeans on date-night.

It can be dressed up or down, and the right pair can be worn for hours without causing blisters or pain. They're the shoes that you'll find yourself gravitating to on occasions where you'd like to feel a little more put-together but not overdressed — which are many.

Unfortunately, shoes require more upkeep due to the amount of time we spend shoving them into the ground. So, if you invest in a pair you love enough to wear often, you may wind up taking on additional tasks to clean them or make them more durable. That's why we recommend paying for one pair that's worth getting resoled a couple of times rather than a few boots that you wouldn't miss.

The jean jacket, like most of the pieces that require time to discover and a chunk of change to buy, is just as acceptable for shade in the summer as a brisk walk around town in the fall. It's easygoing, has great cost-per-wear value, and becomes more unique, personalized, and comfortable with frequent use. It's the kind of thing we love to throw on when we're not sure what to wear.

For those that wear jeans as often as we do, we don't need to explain why a great pair is on this list. If you could spend $100 upfront on denim that makes you feel incredible every time you pull them on, then we'd encourage anyone able to splurge to do so on said magic pair of jeans over a handful of others that you aren't excited to wear.

It may be a good idea to buy one perfect investment pair you adore and a couple of also-great-but-reasonably-priced versions to get you through the laundry week.

For every outing that doesn't require a heavy tote, but could use space for more than the lip balm and keys in your pocket, the answer is a midi bag. And, ideally, one that can be worn as many ways as possible — crossbody, over your shoulder, and perhaps as a clutch too. This is also an item where fewer and better is advisable. Diversity and accent pieces are great, but if you're relying upon something for its functionality, why not just use the best and most organized version of it every time?

You'll find yourself in need of sunglasses more often than you'd expect, and ideally, you'll want a pair with UV-blocking protection and polarization (which takes care of glare).

It can take a long time to find a pair of sunglasses with exactly the right proportions and shape for your face. Which is why it's smart, in the meantime, to commit to something pretty universally attractive — like a wayfarer or round frame.

If we could only choose one thing to wear in the fall and winter, it would probably be the cashmere sweater. It's soft, timeless, and cozy enough to feel like you're being hugged by a blanket all day. With care, you can own the same one for years to come and, if you opt for a dark neutral color, you can probably get away with wearing it at least once a week without anyone being the wiser.

• The best cashmere sweaters you can buy
• Everlane's cashmere crew neck sweater is the backbone of my winter wardrobe — and it's only $100

Like midi bags, the work tote falls decisively into the category of "fewer, better." At the end of the day, you need something that carries your work essentials (a laptop, notepad, pair of headphones, charger, wallet, etc.), organizes them into a system that minimizes stress instead of creating it, and is comfortable to carry. Ideally, the color and material will also work with a majority of the workwear in your closet. Before buying, take a look at your closet to see which palette you should stick to.

• This tote that keeps selling out is the ultimate work bag for professional women

Tied with the walkable bootie for the most versatile footwear is a pair of flats that can be dressed up and down — particularly, any pair that won't require undue amounts of break-in time and goes with most outfits and occasions. And, if you're going to splurge on a luxury version of anything, you'll get the most practical longterm use out of frequently worn accessories in neutral colors — like your shoes and bags.

• Everlane has a $98 women's flat made of recycled plastic bottles — it might be the most comfortable pair we've ever tried
• Everlane's $115 Day Glove flats look and feel like they cost a lot more — here's what we think after wearing them around New York City for a year
• I put 5 of Everlane's bestselling shoes to the test in NYC and ranked them by comfort level
• I wear the popular Everlane Day Gloves at least 3 times a week — here's why I think they're the best flats you can buy

One life is about two lifetimes too short to be uncomfortable, but there will be occasions in which wearing heels is necessary or desirable. For those events, it makes sense to invest in a pair that you really love, and which come with the kind of insole and heel height that you can spend a few hours in without needing to take a cab home early.

• Everlane's popular Day Heel is low enough that you can actually walk in it all day — but you'll want to be careful about sizing

Everyday jewelry pieces don't need to be placeholders for something nicer. Thanks to jewelry startups that cut out traditional costs, if you have $50 to spare you can get yourself a pair of dainty 14k yellow gold earrings over a few $25 pairs you don't care about. Instead of buying cheaper versions for short-term wear until they turn green in the shower and need to be replaced, you can buy basics like hoops or a fine chain necklace once — and then build on that functional base over time.

• The best places to buy affordable fine jewelry
• Popular jewelry startup Mejuri is one of the most affordable places to buy everyday pieces, from gold hoops to stacking rings
• AUrate used its customers' feedback to create a stunning new collection — here's your first look
• Stone and Strand makes beautiful, minimalist gold jewelry that looks good online and even better in person — here's how its dainty pieces stack up

You can wear it to work, to date night, and to nice events out on the town. Along with being better looking than a puffer, an overcoat will never go out of style and you can wear the same classic version for years to come.

• Everlane's new recycled wool coat has a simple and versatile silhouette with a few elevated details that make it stand out — here's what you should know before ordering it

A button-up is another classic that can be dressed up or down indefinitely. It can transition from relaxed and laidback over jeans or a swimsuit to polished and cool tucked into a suit. The best versions will distribute volume in a way that keeps the shirt's torso loose and the shoulders tailored, so you get a look that's refined without overwhelming your shape.

See number 11: "A pair of comfortable, low heels" again. Life is too short for underwire that pokes you whenever you breathe or a bra that's actually the wrong size. If there's anything worth investing in, it's the comfortable version of the items you wear every day — and it's a bonus if it can make everything worn on top look better, too.

When it comes to undergarments, our advice is to go and get fitted in person once a year (ideally at a specialty store with lots of experience, and not a Victoria's Secret), and treat yourself to a bra that makes life a little bit easier — by making you feel more comfortable and even more confident.

• The best bras of 2020
• ThirdLove's cotton T-shirt bra is so comfortable you'll forget you're wearing it — here's how it's held up after one year of testing
• I finally found a supportive, unlined bra for larger cup sizes, and I wear it with everything
• A lingerie startup used feedback from 6 million women to make the perfect wireless bra — and it works for larger cup sizes

Not many wardrobe items are so iconic that they earn an official acronym, but the little black dress (LBD) is one of them. It's universally flattering, versatile, and timeless. You can buy one now and wear it for cocktail parties, swanky events, nice dates, and whatever formal affairs life throws at you, especially the last-minute ones.