light wash jeans outfit

Classic Fashion Master List | My All-Time Favorite Clothing Pieces

Please note that this post may contain affiliate links and any sales made through such links will reward us a small commission – at no extra cost for you.

Where should you start when refreshing your style, building a wardrobe, or elevating your look? You start with the basics. Finding the right basics takes time and trial and error. Lucky for you, I’ve made finding the right basics my job! This is my classic fashion master list.

The clothing items that made this list are the staples I believe make up classic fashion and are ones that I could envision other women wearing and loving, no matter the age. These are the items that I’ve had for a while and have frequently worn.

If you don’t see something on this list that I’m frequently photographed in, it doesn’t mean I don’t really love it! A lot of my favorites are from thrift stores. Also, a girl has got to draw the line somewhere to avoid this post turning into a book instead of a curated list haha. (Which kind of already happened- whoops.)

I’ll link to the exact things when I can, but the “problem” with holding onto items in your wardrobe for years, shopping slow, and thrifting means that items eventually go out of stock or get replaced by a newer version for the latest season. I will offer alternatives when applicable.

But bookmark this post because I plan to add to it over time as things come back in stock and/or as I try out more staple items!

Classic Fashion Master List


Halogen Crewneck Cashmere Sweater
A great price for a soft and beautiful 100% cashmere sweater.

Alternative: $50 Mongolian Cashmere Crewneck Sweater

Port Authority Women’s Long Sleeve White Poplin Shirt
Great value for a well-fitting staple item.

Skims Cotton Jersey T-Shirt (Soot)
This is very fitted, but it’s so soft on the skin and makes a great layering piece.

Gap The Modern Crewneck T-Shirt & Banana Republic Luxe Touch Crew-Neck T-Shirt
Thanks to my experiment on finding the best white t-shirt, I found many new favorites. These are my current faves.

Mango Striped Cotton T-Shirt
This style is more boxy than fitted, but I like the casual aspect of it. It also says navy, but it mostly looks black to me!

J.Crew Striped Boatneck T-Shirt
Simple yet feminine and classic too!

Honorable Mentions:


Madewell Classic Straight Jeans in Nearwood Wash
The perfect classic straight jeans you’ll never regret owning.

Madewell The Perfect Vintage Jean in Fiore Wash
Very comfortable and the perfect relaxed fit and wash for the warmer months.

Everlane The ’90s Cheeky Jean Ankle
A similar style to the aforementioned Madewell jeans, but no stretch. However, that can be a good thing as a little rigid fit can hold you in!

J.Crew Pull-On Slip Skirt
For easy, effortless (and comfortable!) outfits.

Everlane The Way High Jean
For a refreshing take on the slim silhouette, choose these fun wide-legged jeans!

Everlane The Way-High Drape Pant
I’ve only had them for a few months so I can’t speak to the longevity, but they’re pictured in this post multiple times because I love them! I got my normal size and they are a little loose in the waist, so keep that in mind. They look elevated but they’re comfortable too. Definitely going to order more!

Honorable Mentions:

  • I don’t think everyone needs leather leggings, but the Spanx Faux Leather Leggings are bottoms that are on repeat every fall & winter for me.
  • The Good American Good Straight jeans have been in my top for many years and though I still love them for their stretch, Madewell & Everlane jeans have stolen my heart just a little bit more.


Everlane The Japanese GoWeave Slip Dress & Quince 100% Washable Silk Slip Dress
I’ve got two slip dresses that I both love equally for different reasons. The one from Everlane is longer and feels more like cotton, which makes it more casual and relaxed. The one from Quince is shorter and silkier, making it a bit more upscale.


The ’80s Blazer
Perfectly oversized. It shouldn’t replace your fitted blazer necessarily, but a style like this is great for casual-chic outfits.

Mango Wide Lapel Wool-Blend Coat
This coat is the perfect thickness. The color is great and I love the belted feature. So classy! Keep in mind that there are silver magnet clasps to help keep the coat closed, so they would be shown if you wanted to wear it open.

Everlane The Gathered Drape Trench
My all-time favorite trench coat from Everlane is an old product, unfortunately, and currently, this is the only other trench coat I have. I don’t like it as much as my original, but it has grown on me and I find myself reaching for it a lot. However, there is still mainly one thing that I’m not thrilled about- the inside lining of the pockets hangs out when the coat is open unless you make a conscious effort to keep tucking it back. If you’re not nit-picky like me it may not bother you!

J.Crew Schoolboy Sweater-Blazer
This is a go-to piece for casual-chic occasions. The silhouette says chic, but the material says casual. The perfect thing to wear when you want to look elevated, but not out of place.

H&M Double-Breasted Jacket
The pearl buttons on this blazer dress it up and elevate it so well!

Honorable Mention:


Everlane The Modern Loafer
I will say that these loafers pinch my feet a little, so why did they make the classic fashion master list then you may be wondering? Well, I bought these shoes when I was pregnant and my feet went up a size (and stayed that way-joy). So they are simply a little too small (as are most of the shoes in my wardrobe now).

But I push through because not only is the camel color beautiful, but they are so sturdy and well-made.

Circus by Sam Edelman Charlotte Ballet Flat
If you want a classic ballet flat that feels like walking on a cushion, these are the shoes for you.

The Day Boot
The perfect heel height for everyday wear. Easy to clean. Super soft. And pretty comfortable, as far as heeled boots go. Definitely one of my absolute favorites!

Sam Edelman Women’s Aubrie Sneaker
I own a lot of Sam Edelman shoes…they are just so comfortable to me! This is a Golden Goose-inspired shoe that is simple yet interesting.

French Sole Cognac Leather Sandal
They got a little scuffed during our move (for the price I wish it wouldn’t have happened so easily), but I still love the style and the comfort.

Sam Edelman Women’s Laguna Chelsea Boot
Classic style in a pretty color. Love wearing them with my leggings and jeans.

Sam Edelman Larina Waterproof Knee High Platform Boot
Sturdy, practical, and perfect for a trendier boot when you live in the midwest and need snow and rain coverage!

Everlane The ReLeather Tennis Shoe
Full transparency, these rub a little bit on my ankle (reviews say they’re stiff at first), otherwise, they are comfortable and fresh. I like that these are easier to keep clean than canvas sneakers!

Honorable Mentions:

  • The Madewell Boardwalk Lace-Up Leather Sandals are about as comfy as they look (so just so-so), but I LOVE the style!
  • Who woulda thought I’d have Teva Midform Universal Sandal as favorites? They are just so comfortable and I like pairing them with my dressier items like slip skirts for a unique look.
  • My most worn black loafers and black mule slides can not be linked anymore because they’re so old! However, they’re from Target and these loafers are the newest version from A New Day. (Though I haven’t tried them.)


I have a few straw bags from this small shop on Etsy and they’re worth the wait. They’re handmade, beautiful, and give Loewe vibes.

Karl Lagerfeld Paris Agyness Lamb Shoulder Bag
For the Chanel look on a budget, Karl Lagerfeld bags are for you if you still want a well-made item. (Coming from someone who has both.)

Lancaster Paris Ikon Shoulder Bag
Easy to keep clean, roomy, and neutral enough while still being interesting.

Honorable Mention:

  • This Cuyana Oversized Double Loop bag is definitely a repeat and go-to, from traveling to even being used as a diaper bag. However, it’s worth mentioning that it was gifted to me and if you’re paying for it out of your own pocket, you’ll find it to be pretty pricey.


Madewell Chunky Medium Hoop Earrings
Earrings that go with everything, don’t hurt your ears, and look perfectly simple.

Madewell Ancient Coin Necklace
One of the only necklaces I wear come spring & summer.

Toggle Chain Necklace Set
Love that these all look good together or can be broken up and worn separately too. (Note- it’s been a few years and they are starting to look worn a little bit)


Butterfly Semi Cat Eye Sunglasses
These sunglasses are really affordable and such a chic shape!

Clothing Items I Want to Try/On the Hunt For:

newsletter sign up resource library

Up Next: Classic Style Tips to Steal from Audrey Hepburn’s Outfits | Recreating 5 Timeless Looks

classic fashion master list
classic fashion master list
Carolyn Arentson
Carolyn is the founder and creator behind My Chic Obsession. When she's not dreaming up new content, you can find her watching a funny tv show with her husband, raising her two boys, or planning her next trip to Paris.