Trust Us: These 13 Classic Investment Pieces Are Worth the Splurge

collage of katie middleton, michelle obama, jackie o

KCM/Getty

They’re endorsed by style icons like Princess Diana and Michelle Obama. 

Sure, snagging a $10 puff-sleeved top from Amazon will bring you some quick thrills, but will that item still look on-trend in a year or two? Or is it something that’ll seem dated as soon as fickle fashion tastes change?

Classic fashion staples and accessories are timeless for a reason: They can be styled to suit myriad aesthetics, can be passed down from generation to generation, and will make you look stylish for many years to come. Signature pieces like a crisp white blouse, penny loafers, or dazzling gold hoops will always outlast trends, especially when you opt for well-made, high-quality products. A leather crossbody bag, for example, only gets better with age.

Style icons are proof that signature pieces and capsule wardrobes are forever. Whether you aim to emulate Lady Di’s iconic sportswear looks, dress as chicly as Jackie O, or embrace the coastal grandmother aesthetic, timeless fashion choices will pair seamlessly with your closet go-to’s, making them worth the extra investment upfront. But what are these items, exactly? 

Read on to see 13 essential fashion pieces that never go out of style.

1. Crisp White Blouse

Style icons from Diane Keaton to Grace Kelly to Carolina Herrera and Michelle Obama have all embraced the power of a crisp white blouse. Whether you like yours oversized or trim, prefer wearing it loose or tucking it into a pair of jeans, a white blouse is a must-have top in every fashionista’s collection.

Reformation Will Oversized Shirt

Shopbop

We love a blouse with a roomy fit, and this Reformation top made from stretch poplin delivers on that front, with modern style to spare.

$128 at Reformation

Quince Washable Stretch Silk Notch Collar Blouse

Quince

The only thing better than a silky white blouse is one you can machine wash. Reviewers said this Quince blouse has a “fabulous fit and feel” and confirmed that it’s “high-quality.” Stock up on a few different colors while you can.

$70 at Quince

2. Flattering Denim

Denim’s a part of America’s fashion DNA and has been our go-to fabric since miners first started wearing it during the Gold Rush. Keeping a high-quality pair of jeans on rotation in your wardrobe offers endless styling opportunities. Throw a blazer on with booties and you’ve got yourself an effortless date night look. Wear your jeans with an oversized cardigan and a fresh pair of sneakers, and you’re out the door and on your way to the farmer’s market. Easily dressed up or down, well-made denim (in any wash or cut that suits you) will endure. 

Pistola High-Rise Classic Straight Jean

Pistola

A straight leg style in a dark wash is an immediate yes for us. This slightly cropped Pistola pair shows off a little ankle, whether you’re wearing strappy heels or booties.

$158 at Pistola

Madewell Curvy Plus Perfect Vintage Straight Jean

Madewell

Madewell invented an inner lining in its jeans called “Magic Pockets” — and it’s truly the work of a design wizard. The pockets are constructed to hold you in (in all the right places), while leaving you with a smooth fit that feels like the jeans were made just for you.

$100 at Madewell

3. Trench Coat

Everyone from Kate Middleton to Audrey Hepburn to pretty much every woman in Paris knows that a long trench is a go-to accessory for warding off a light chill in style. Elongating and elevating at once, a neutral trench can be easily thrown on over any outfit when the temps aren’t sub-zero. (On those dreary days, we won’t blame you if you reach for your warmest puffer.)

J.Crew Icon Trench

J.Crew

Who does the classics better than J.Crew? Olympia Gayot, the brand’s new head of women’s design, is putting J.Crew back on the fashion map and the brand’s new Icon Trench is helping it stay on task.

$348 at J.Crew

Lattelier Knee-High Trench Coat

Lattelier

New to the scene, Lattelier has a simple mission: “Elevate what everyday clothes can be.” We’re loving the brand’s double-breasted, knee-length take on the classic trench.

$169 at Lattelier

4. Throw-on-and-Go Blazer

Blazers are a gift from the fashion gods. Want to feel instantly sophisticated? Throw on a blazer over jeans and a tee. Looking for an effortless day-to-night ensemble? Pair a blazer with your crisp white blouse and favorite trousers. There’s no question here — blazers win. Always.

Cinq à Sept Khloe Ruched Sleeve Blazer

Nordstrom

If you’re looking to splurge on a blazer you’ll reach for several days a week, look no further. Cinq à Sept nailed this design: The sleeves are perfectly ruched (no need to keep adjusting them throughout the day, thank you very much), with the perfect modest length for days when you feel like covering up.

 

$395 at Nordstrom

Vetta Convertible Blazer

Vetta

A blazer and vest in one? We love a garment that’s multi-functional. Perfect for travel (because you get two totally distinct looks), this brown plaid blazer will pair seamlessly with your favorite bottoms.

$188 at Vetta

5. Menswear-Inspired Shoes

When it comes to classics, take a cue from the menswear playbook with styles that go back decades. Time has proven that a classic pair of loafers and Chelsea boots will always be of-the-moment.

J.Crew Rowan Penny Loafers

J.Crew

“Oh god, they’re perfect,” writes one reviewer. These are like the shoes your dad used to wear to work, only better. We’re not sure what to love most: the chunky heel, the glossy leather upper, or the penny-holding pockets.

$80 at J.Crew

Nisolo Everyday Chelsea Commuter Boot

Nisolo

Cue up Nancy Sinatra’s “These Boots Are Made for Walkin’” as you slide into these slightly pointed slip-on Chelsea numbers. They’re so comfy, you won’t be anxious to take them off even after a full day of strolling.

$200 at Nisolo

6. Leather Bag

When it comes to toting around your essentials, a chic black crossbody bag will always get the job done. Who doesn’t love this hands-free, no-hassle style? For larger hauls, a durable leather tote is essential. And the best part about investing in a leather bag is that knicks and scratches give the bags their personality over time. Plus, their enduring stylishness means future generations will cherish them as prized possessions for years to come.

Coach Kip Turnlock Crossbody

Coach

Coach is synonymous with high-quality leather goods. The purse mecca has sold a variation of their classic Kip Turnlock bag for decades (so you know they’re well-made). This smaller option features a strap for crossbody occasions, but it’s easily removable if you want to use the top handle on a night out.

$250 at Dillards

Cuyana Classic Easy Tote

Cuyana

A polished tote bag might seem like an oxymoron, but just try this Cuyana tote on for size. It’s classic and easy, as the name suggests, and will get you from points A to B with a sophisticated flair.

 

$248 at Cuyana

7. Little Black Dress

Designer Karl Lagerfeld once said, “One is never over-dressed or under-dressed with a little black dress,” and we agree. The right LBD, especially in a sheath style that gives you a little breathing room, is a wardrobe savior. Invest in one with high-quality fabric and you’ll never look back.

Theory Sheath Dress

Theory

What is it about the perfect LBD that does the heart and soul so much good? (For one, it makes getting dressed easier.) This short-sleeved style from Theory is ideal for wearing under a blazer, leather jacket, or cozy cardigan to pretty much any activity on your agenda.

$245 at Theory

Tuckernuck Black Crepe Kenzo Dress

Tuckernuck

LBD’s don’t have to be boring, which this Tuckernuck style proves. It’s difficult to count the number of ways you can style this V-neck, three-quarter-sleeved frock, but here are two suggestions: 1) Add some gold jewelry and a fun clutch, and you’ve got your holiday office party look. Or, 2) throw on some tights and a pair of knee-high boots and you’re ready for happy hour.

$128 at Tnuck

8. Cashmere Sweater

Few things feel as luxurious as slipping into a cashmere sweater. No matter the shape, style, color, or cut, investing in a trusted cashmere piece is a no-brainer. Not only does the material soften with wear, but it’ll also keep you warm and last for years when you take good care of it.

Jenni Kayne Cocoon Sweater

Jenni Kayne

This cuddly cashmere cardigan from Jenni Kayne is slightly oversized for a lived-in look and feel, but not so big that you’ll feel like you’re drowning in it. You can easily wear it open, buttoned-up, cinched with a belt, or tied around your shoulders — the styling possibilities are endless.

$445 at Jenni Kayne

J.Crew Ribbed Cotton-Cashmere Relaxed Turtleneck Sweater

J.Crew

J.Crew combined our two favorite fabrics — comfy cotton and cozy cashmere — and used their design magic to create one of the softest turtleneck sweaters ever. We love this heather gray hue, but you can take your pick from black, rose, navy, and cream, too.

$55 at J.Crew

9. Classic Jewelry

Why are hoops, pearl studs, and a classic chain necklace considered timeless pieces of jewelry? Because they’re subtle enough to sparkle without making a huge statement, so you can wear them with any outfit. These are the kinds of seasonless accessories every woman needs in her jewelry box.

Jennifer Fisher Lilly 10K-Gold-Plated Micro Huggie Hoop Earrings

Saks Fifth Avenue

Ever put on an outfit and wondered, How do I make this less boring? Try adding an easy gold hoop to the mix, and giving your ‘fit a little extra pizzazz. We’re partial toward these hoops by jewelry designer Jennifer Fisher, who crafts minimalist, no-frills, fine and fashion jewelry.

$150 at Saks

Lagos Luna 8mm Pearl Stud Earrings

Nordstrom

Yes, they’re pricey, but if you wear these pearl studs just 20 times in your lifetime, the cost per wear will be just $10. Investing in “real” jewelry is always a smart idea because it won’t tarnish, rust, or break easily. Plus, you’ll cherish these heirloom studs forever.

$200 at Nordstrom

Brinker and Eliza Carson 24K Antique Goldplated Necklace

Saks Fifth Avenue

If you want to layer necklaces (all the rage these days) but avoid them getting tangled together, choose ones with varying weights. This 24-carat gold-plated chain is heavy enough to stay in place and not cause a ruckus among its counterparts, but it’s also versatile enough to add a touch of glamour to any daytime or nighttime look.

$108 at Saks

10. White Sneakers

Some say Paris is always a good idea — we say the same applies to white sneakers. Not only do well-made ones feel like walking around on a pillow, but they can be the starting point for a number of outfits. Whether you’re traveling, headed out to dinner, or just running errands, these versatile shoes will keep you looking fresh and feeling cool.

Thousand Fell Classic Sneakers

Thousand Fell

Using innovative materials and a comprehensive recycling program, Thousand Fell makes go-to white sneakers that’ll be the most sustainable item in your closet.

$125 Thousand Fell

Vince Blair Perforated Leather Slip-On Sneakers

Saks Fifth Avenue

Prefer a slip-on style? This leather pair by Vince will last for years and keep blisters at bay.

$200 at Saks

11. Simple Sunglasses

When you’re heading out the door, it’s nice to have a classic accessory on hand to throw on. Enter: Simple sunglasses. While we love the occasional cheap pair, higher-end ones tend to last much longer (and make you triple-check for their location each time you leave a dinner table). They’re classic and cool, as everyone from Jackie Kennedy to the characters in Top Gun prove.

Tory Burch Square Sunglasses 

Amazon

Style icon Jackie Kennedy was always shielding her eyes from camera flashbulbs in sunglasses much like these. They ooze ’70s glamour for any occasion, even if you’re not being hounded by the paparazzi. And though they’re retro, these still look deeply modern.

$142 at Amazon

Ray-Ban Original Wayfarer Polarized Sunglasses

Ray-Ban

The classic Wayfarer has been a trendsetting style since it was first introduced in the 1950s. It’s the epitome of cool, and this iconic shape is one of Ray Ban’s most popular items to this day.

$163 at SH

12. Stylish Weekender

You know what’s better than traveling? Traveling with a monogrammed weekend bag. In the same way that a classic everyday purse is a worthy investment, a high-quality (and better yet, sustainable) travel bag will be an essential companion every time you hear the siren song of the airport. This bag keeps your things tidy and organized while letting the world know you have taste.

Paravel Weekender

Paravel

Catapult your weekend travel bag into a league of its own with Paravel’s Weekender bag. Made from durable, spill-proof canvas (thanks to 12 upcycled water bottles), they can be monogrammed for an extra personal touch.

$295 at Paravel

13. Matching PJs

Instead of wearing the same old pajamas all the time, why not spice things up? A matching pajama and robe set makes for a great gift to yourself. Plus, when you invest in high-quality cotton, you’ll sleep like a baby.

LAKE Pima Long-Long Set

LAKE

“The most comfortable part of your day should be celebrated” is sleepwear brand LAKE’s motto. We couldn’t agree more. This two-piece pajama set comes in two lengths (regular and cropped) and it’s made from 100 percent Pima cotton, which helps ensure you’ll have the dreamiest of nights.

$124 at LAKE

LAKE Pima Robe

LAKE

We love LAKE pajamas, but their robes make even the drabbest days feel like a getaway. Snag this Pima cotton robe in a print that matches your PJ set and you’ll be checking yourself out in the mirror even before you’ve hard your morning coffee.

$136 at LAKE