Classic Outfits: Timeless Fashion Choices (Plus 45+ Outfit Ideas!)

This post will guide you through mastering classic outfits in 2023.

A while back, we covered 15 boho chic pieces you ought to have in your closet to help build a bohemian wardrobe. However, after reading your responses, I realized the need for another, more fundamental and basic list–so here it is!

In this post, I will cover the most timeless and basic pieces you need to create an awesome, classic wardrobe. These are the basic building blocks of a well-rounded closet.

You’ll notice that many of these are also on our college wardrobe essentials list. However, this list is shorter, less college-specific, and includes career staples for your post-college life.

These are definitely investment pieces, so don’t be afraid to splurge on certain ones if the time is right. They’re classics and (if you take care of them) can last for years or even decades. They’ll carry you through work weeks at a big girl job, dinners with significant other’s parents, networking soirees, and so much more.

And without further ado, let’s jump right into our classic styles clothing guide!

Related reading: How to Build a Wardrobe That is Stylish & Functional

1. A Little Black Dress

Every magazine, fashion blog, CF writer, and even your mother was right. Having a trusty LBD in your closet is crucial for nailing classic style.

Look for classic knee-length sleeveless sheath styles, similar to something you could picture Jackie O or Audrey Hepburn wearing. Ensure it’s not too short and doesn’t show cleavage for the ultimate versatile piece.

Also Read: The Ultimate Feminine Capsule Wardrobe (Girly Wardrobe Essentials)

This short-sleeve Amazon dress (left, above) has thousands of 5-star reviews and absolutely nails this aesthetic! It’s also under $40, a total steal!

For a more formal look, the long sleeve dress from Nordstrom (right, above). Also, clocks in right around $50 and has a more glamorous, sultry vibe.

Here are a few ways to wear an LBD:

• A little black dress plus pumps, pearls, and a (#2) cardigan or (#8) blazer equals an instant and perfect business casual look.
• For a sassy date night ensemble, wear your LBD with a sexy pair of stilettos, a top knot, and a chunky chain necklace.
• Layer your LBD over a (#3) white button-down shirt to give your dress an entirely new look!

Related reading: The 5 Types of Classic Dresses That Will Always Be in Style

2. Basic Cardigans

From thin cashmere to durable cotton to heavy wool knits, there’s a cardigan out there that will perfectly fit your needs no matter the occasion or season.

I love cardigans because they can be styled to look any way you want them to. Be sure to pick up several different cuts, fabrics, and styles so you’ll have plenty to choose from.

Here are a few ideas on how to wear them:

• An oversized, long cardigan (like the middle one, above) will give you a cozy vibe when worn with leggings or a (#14) skinny jeans and a (#12) simple v-neck shirt. Finish with a pair of classic white sneakers and timeless jewelry.
• For a sophisticated Hamptons kind of look, drape or tie a cardigan around your shoulders with your favorite (#1) LBD or sundress and a chic pair of wedges or sandals.
• This might not be conventional, but I actually prefer cardigans rather than hoodies or jackets when I go to concerts and football games because they’re thinner and therefore easier to stuff in a purse or tie around the strap of a cross-body bag if it gets too hot.

Related reading: Classy Outfits for Women: How to Dress Classy & Elegant

3. A White Dress Shirt

To be work-ready, for interviews, or a fancy dinner, a white dress shirt should be your new BFF.

Don’t skimp on this item – your white dress shirt should retain its shape after multiple washes and be completely opaque. Also, consider sizing up with cotton clothing to avoid unflattering pulls and gaps around the chest. Better safe than sorry!

I splurged on this white dress shirt from Revolve, which was $79 but it was entirely worth it. I love the luxe-feeling material that it’s made of — it looks much more expensive than it is. Also, I love how it somehow looks fantastic in the most rigid professional dress code. However, still looks amazing and feels comfortable in casual, everyday outfits as well. I highly recommend it!

A few stylish outfit ideas:

• White dress shirts are the ultimate work attire building block. Pair your white dress shirt with a pencil skirt, with a (#8) blazer, with (#11) khaki trousers, with (#13) black dress pants, or even wear one over a (#1) LBD to turn it into a skirt and shirt look. Finish with a statement necklace and simple (#10) pumps or (#4) ballet flats. The combinations are endless!
• For a fast and casual look, wear a white button-down shirt with a pair of mom jeans and Converse All-Stars or Vans.
• Throw one under a sweater or (#2) cardigan for a geek-chic ensemble!

4. Loafers

Loafers are a newly trendy item that’s actually a staple of classic style. They’re buttoned up, formal, and oh-so comfortable, so they’re an amazing shoe to have in your wardrobe.

The trendiest style out there is the ubiquitous loafer mule popularized by Gucci, (the Amazon ones on the left, above, are a great dupe for the Gucci ones!) but if you want to keep it timeless, go for a regular pair in black, taupe, or white.

Here are a few fun ways to wear them:

• Evoke your inner Instagram girl and wear a pair of backless loafers with (#14) skinnies, and a (#3) white dress shirt. For bonus points, add cat-eye sunglasses, red lipstick, or tons of gold jewelry.
• Rock a pair of loafers with a (#1) little black dress, a fedora, and a cute little scarf tied around your neck. Tres chic!
• Loafers can absolutely be business casual, so wear them with (#13) black dress pants, a blouse, and a (#2) printed cardigan over top.

5. A Tan Trench Coat

I’ll be honest, it took me a while to finally bite the bullet and splurge on a classic, timeless tan trench coat.

You can find cheap versions at Forever 21 (and the Amazon one on the left isn’t bad), but I’d recommend saving your money for a quality trench coat from a brand like Everlane (right, above), or, if it’s not out of reach, Burberry. They’ll be cut more conservatively, and will last for years or even decades.

Look for styles that hit below your butt and are cut loose through the sleeves and shoulders, so you’ll be able to layer pieces underneath.

A few stylish outfit ideas:

• Is there anything more gorgeous, chic, and demure than a trench coat worn with red lipstick, a trusty (#1) LBD, (#10) pumps, and a simple bun or ponytail? This look is perfect for dates, dinners, work, or even just adding a bit of mystique to mundane tasks like grocery shopping or going to the bank!
• On the next rainy day, leave that boxy sorority-issued anorak at home. Instead, rock a pair of skinny jeans and any top with a trench coat and an eye-catching pair of boots. Tie a (#9) lightweight scarf around your neck for bonus points.
• Trench coats look awesome buttoned up and tied, but they also look fantastic left open and loose. Try wearing one with a sweater, (#14) skinny jeans, and (#6) knee-high boots.

6. All-White Sneakers

I know what you’re thinking: Sneakers? On a classic style guide?

Yes, I said sneakers. Trust me on this. They are a classic style staple in 2022 and show no signs of going away. Once you get a pair of all-white sneakers, you’ll wonder why you didn’t buy them sooner.

The number of ways you can wear a simple pair of classic white sneakers is virtually endless.

You want these shoes to complement and blend with any outfit, so look for a pair with few to no embellishments. Fashion girl favorites include Adidas Stan Smiths, Keds, and, if you’re feeling like splurging, every Instagram girl’s favorite, Alexander McQueen.

A few stylish outfit ideas:

• Pairing a solid-colored dress, denim jacket, and white sneakers is an easy and stylish look for class.
• Knee-high boots immediately add polish to any leggings, oversized (#12) v-neck and (#2) cardigan combo.
• Skinny jeans and sneakers are a modern day uniform.

7. Black or White Jeans

Although medium wash distressed, boyfriend, and mom-style jeans are more modern, it’s still important to have an oh-so-classic pair of black or white jeans in your closet. These can be slim cut, flared, or boot cut — just make sure they’re simple.

These jeans always come back into style and are great for nice dinners, casual days at work, or even just pairing with a t-shirt.

Look for styles with no fading or embellishments, and if they run long, have them hemmed to hit the bottom of your heel perfectly. If you want to splurge on a pair of designer jeans, a straight or boot-cut pair (I love this gorgeous Agolde pair) is definitely the most timeless option.

A few stylish outfit ideas:

• Wear these jeans with (#10) black pumps and a (#3) white dress shirt for a classic, sophisticated look that’s perfect for meeting the parents or going to a smart-casual work function.
• Nice jeans will look fantastic with a (#8) black blazer and a small (#9) scarf around your neck.
• Wear straight-cut jeans with a bodysuit, a (#2) cardigan tied around your shoulders, and some (#4) mule loafers for an Instagram-ready ensemble.

8. A Perfect Black Blazer

Blazers are awesome pieces because there are so many varieties to choose from. Both shrunken and oversized styles are hot right now, but before you purchase either of those, be sure of have that perfect-fitting classic one in your closet.

Make sure the sleeves hit right at your wrists, and the shoulders have enough room to layer underneath. The front should be fitted, but not pull out around your chest.

A trip to the tailor might be pricey, but is SO worth it when it comes to a timeless piece like this. You need it to nail that classic style.

Here’s a few ways I like to style my blazers:

• Blazers look fantastic over almost any dress in your closet! Finish the look with a simple necklace and pumps.
• One of my favorite night-on-the-town looks is a pair of (#14) skinny jeans, super high stiletto heels, a chic clutch purse, and a tank or bodysuit layered underneath a blazer.
• For a fast and easy outfit, wear a black blazer over one of your favorite graphic tees, a pair of mom jeans, and some (#6) white sneakers. Totally comic-book chic!

9. A Lightweight Statement Scarf

Scarves aren’t something people intentionally buy, but somehow end up with. It’s fascinating how a simple scarf can instantly elevate an outfit, making it more stylish and complete!

For the most flexibility, buy a variety of short and long scarves, square-shaped and rectangular, sheer and opaque. Personally, I don’t like to spend a ton of money on scarves, but I know some girls swear by fantastic designer scarves.

Do what you feel comfortable with and what is within your budget. You can’t go wrong either way!

A few stylish outfit ideas:

• I really love the look of a chic scarf tied in one’s hair. There are just so many cool things you can do with it! Channel a pin-up girl by folding one into a triangle. Wrapping it around an updo, and knotting it right where your hairline meets your forehead. Another cool variation on this is to leave your hair down. Fold the scarf into a 2 to 3-inch band, channeling a sort of hippie-chic-meets-Rosie-the-Riveter vibe!
• A light scarf worn around your neck won’t look old lady-ish as long as you style it with modern pieces. Rock it with distressed boyfriend jeans and strappy sandals for a cute, modern take on a classic.
• Try tying a scarf around a handle on your purse, around your waist as a belt… and let’s be real, they work as face coverings, too. The possibilities are endless!

10. Black Pumps

No girl in the world should go without a pair of wearable, classic, and simple black heels in their closet.

These babies will be here for you from weddings to sorority functions and from first dates to first jobs. Look for very simple styles with no embellishments, and look for a 2-4-inch thin to medium heel. (The Sam Edelman pumps on the left, above, are closer to 4 inch — despite this, they’re my all-time favorites for comfort — while the Lifestride pumps on the right are 2.5 inch.)

Personally, I’m not a fan of kitten heels, but if you have trouble walking in tall shoes, do what you need to do to stay comfortable. The key to looking classic and chic is staying poised and believe me, I understand how impossible that is if your feet are killing you!

A few stylish outfit ideas:

• Your favorite (#1) little black dress will look amazing with
• Have a hot date immediately following a professional club meeting or business function? Wear a tank top blouse, pencil skirt, and awesome black heels. Layer on a (#8) blazer for the meeting, and take it off for the date! Bonus points if you add a belt or a cool portfolio purse.
• Black heels do an amazing job complementing dressy shorts. Tweed, leather, and silk styles are my favorites. Finish with a sheer button-down blouse and cat-eye liner.

11. Denim Jacket

In the past, denim jackets might have been associated with middle schoolers and cowboys, but I promise — they have a place in a modern fashion girl’s wardrobe! In fact, they’re a must if you want to get that classic style.

Denim jackets are the sartorial version of a bowl of plain pasta — a blank canvas that you can pair with basically anything!

Here’s a few ways I’d wear them:

• Rock one over your favorite (#7) white jeans and a (#12) v-neck tee, then add sandals and gold jewelry for the perfect late spring/early summer outfit.
• A denim jacket is the perfect pairing for a (#1) LBD. Add some (#6) white sneakers and a slouchy clutch bag for a casual dinner out.
• Embrace the sweet, preppy vibe of a denim jacket and pair it with a white sundress and (#4) white open-back loafers. Finish with a (#9) scarf tied around your ponytail.

12. Simple V-Neck Shirts

If I had a dollar for every v-neck tee I had in my dresser, I’d be able to buy at least three more!

V-necks are fantastic for layering under jackets, lounging around the dorms in, or using as base pieces to help tone down statement extras. I don’t like to spend a lot of money on v-necks because, at least in my humble opinion, a t-shirt is a t-shirt.

My favorite v-neck is the leopard pocket one on the right, above — I love that the sleeves are a little longer and slouchier than your usual t-shirts. This makes it so flattering and easy to pair with anything!

No matter what tee you get, though, you can’t go wrong. I know girls who swear by the 5 packs of Hanes mens v-neck tees you can get on Amazon or at Target. No shame!

Here’s a few ways I like to wear basic v-neck tees:

• There’s no outfit easier or breezier than a v-neck paired with jeans or shorts, (#6) canvas shoes, and a baseball hat. Talk about classic style.
• Wear under a cardigan or a blazer and with a pair of (#14) skinny jeans and some (#4) loafers for a fast outfit that’s comfy but still nice enough for class.
• Layer a v-neck under a sweatshirt or an oversized knit sweater to – hear me out – absorb any residual armpit or back sweat-age that could happen, and keep you dry and comfortable all day.

13. Black Dress Pants

Okay, if you’re like most college girls, you might not immediately see a use for black dress pants in your closet. But these pants are like having cans of tuna or tomato soup in your pantry — an absolute must-have for emergencies! They’re a classic style essential.

Take your pants to the tailor and have them hemmed to hit the edge of your foot. This way, they can be worn with both heels and flats.

Look for styles that fit loosely throughout the thigh and flare out oh-so slightly around the calves. Honestly, I’ve got to salute Express for making durable, stylish, and classic dress pants that are also very fairly priced.

Also, if you can swing it, buy your black dress pants and (#8) black blazer together as a suit so they’ll match perfectly.

Here’s how I wear mine:

• Even if you didn’t get them at the same time or from the same store, pairing black dress pants with a blouse and your classic (#8) black blazer will make for an instant business suit.
• These babies will look awesome with a (#3) white dress shirt tucked in, and a (#9) bright scarf tied around your neck or even in your hair. For more fun twists, add bright lipstick or a cool pair of earrings.
• Although the most practical places to wear black dress pants are business and work situations, you can bring them out for a night on the town too! Try pairing them with wild high stilettos and a crop top, or even with a black waistcoat for a chic play on a tuxedo.

14. Classic Wash Jeans in the Cut of Your Choice

Black pants serve as the staple Campbell’s Tomato Soup in your wardrobe, while denim jackets play the role of versatile dry pasta. Classic outfits, represented by classic wash jeans, act as the essential table salt, complementing and enhancing any ensemble effortlessly.

It surprises me that high-waisted, light to medium-wash jeans were considered a passing trend not long ago. I remember once thinking that only dark-wash skinny jeans were flattering! Years have passed, and we all know that mid and lighter washes and wider leg styles are here to stay. (Although I still love my skinnies, too.)

The moral of the story? All classic washes, from light to dark, work here. Minimal distressing is the most timeless choice, but branch out according to your personal style. Skinny jeans are great, but if you’re feeling a wider leg, go for it! You can’t go wrong if you keep the wash classic.

You can find well-fitting jeans all over the place. I like styles that allow a little circulation throughout the groin and hip area. So, that they stay comfortable all day.

A few stylish outfit ideas:

• Light wash skinny jeans like the ones on the left, above, look amazing mixed with other light pieces. Pair a cream (#2) cardigan with a white bodysuit and finish with (#4) loafers.
• Straight leg jeans (center, above) are my current obsession. Wear them with a (#8) black blazer, (#10) pumps, and a tank or crop top for a cool-girl nighttime look.
• This outfit is incredibly obvious, but classic jeans look amazingly awesome with a comfy tee and (#6) white sneakers. Switch up this combo by adding an oversized cardigan. Swapping the tee for a (#3) white button-down shirt, or adding a (#5) trench. Finish with loose waves and nude lipstick.

15. A Wool Coat

In colder regions, a must-have for winter is a classic outfits-inspired wool coat for women.

I love shopping for coats! You could be rocking a raggedy t-shirt, a diamond-studded bra, or nothing underneath, and no one would ever know!

While I usually opt for edgier (faux) fur coats, my classic, preppy wool coat is a go-to during winter. A dressy wool coat is essential for business or formal occasions in winter.

Check out these cute outfit ideas:

• You’ll look East Coast preppy chic with a wool coat buttoned up over a striped scarf. Finish with winter boots, and a beanie in a coordinating shade.
• Finding coats long enough to cover dresses is key. These wool coats look amazing over a winter cocktail dress and tights, adding a structured and classic touch. Perfect for those last-minute occasions!
• Don’t feel boxed in by all the navy blue and black coats you see. I love my camel coat! I’ve seen girls on campus rock the heck out of blush pink, light gray, and even red wool coats. Since it’s a coat, you don’t need to worry about being matchy-matchy with the colors in your outfit. So go for the coat that speaks to you!

Even More Style Guides:

Classic outfits, not your thing? Check out our other style guides to find the must-have pieces for YOUR aesthetic.

• Wardrobe Essentials for Preppy, Girly, and Sophisticated Style
• Wardrobe Essentials for Street Chic Style
• Wardrobe Essentials for Boho Chic Style
• Wardrobe Essentials for Edgy, Rocker-Chic Style
• Wardrobe Essentials for Electro-Urban Style
• Wardrobe Essentials for Casual, Androgynous-Chic Style

Thoughts on our classic outfits guide?

Do you have all of these pieces? Some of them? Can you think of any basic fundamental pieces that we left out? Are these items just your style, or do you prefer edgier, trendier, more urban, or more boho looks? What other “building block” pieces do you have in your closet? What are some of your favorite ways to wear these pieces?

Leave a comment and tell us what you think about this guide. Also, be sure to check out our boho chic version of this post from a few weeks ago. Can’t wait to hear what you girls think!

Editor’s note: This post was originally published in 2013; it was completely revamped in 2023 with updated items and tips.