Whether You're 25 or 65, These 9 Timeless Outfit Formulas Are Perfect for Autumn

The greatest flex an avid shopper can have is that the item they just bought is worth its weight in gold. For me, this sensation occurs when I've purchased an item I know I'll wear for life. I am so confident in so many pieces in my wardrobe, and I take pride in knowing that one day I'll pass them down to my future daughter (crossing my fingers she is into the whole fashion thing).

With this love for timeless fashion in mind, I am always looking for new ways to style the forever pieces that hang in my wardrobe. For this I head to Instagram, which is home to an abundance of stylish dresses that work up new and interesting ways to wear the classics. The below outfits are ones I plan to copy for many decades to come and will be adding to my saves ASAP. 

1. A Button-Down Shirt + Loose Denim


(Image credit: @greceghanem)

Style Notes: You can never go wrong with the classic combination of a button-down shirt and jeans. The best way to make it feel current is to opt for relaxed silhouettes. Plus, wide-leg denim is a must-have for this upcoming season.

Shop the look:

2. A Relaxed Blazer + Slip Dress


(Image credit: @hannamw)

Style Notes: The idea of pairing a roomy blazer with a slip dress is one that never goes out of style. Dress this versatile look up with heels and jewellery or make it casual with trainers and a sweatshirt. 

Shop the look:

3. A Cardigan + Straight-Leg Jeans


(Image credit: @anoukyve)

Style Notes: A cardigan set is always a head-turner, so don't be scared to invest in a piece like this. Paired with dark-wash denim, it has a '90s-supermodel aesthetic.

Shop the look:

4. A Power Suit + Shoulder Bag


(Image credit: @KAITY_MODERN)

Style Notes: There's a reason they call it a power suit. Your energy will be unmatched the second you put this look on, no matter what age you are.

Shop the look:

5. A Midi Dress + Boots + A Blazer


(Image credit: @frannyfyne)

Style Notes: A dress-boot-blazer combo is so classic. Whether you choose a knitted or floral midi and cowboy or knee-high boots, there are so many ways this look can work with items you most likely already own. 

Shop the look:

6. A Striped Knit + Denim + Trench


(Image credit: @chiarasatelier)

Style Notes: No matter the season, stripes are always a winner. Pair a sweater with denim and a trench coat for a Parisian look that just doesn't date. 

Shop the look:

7. Tailored Trousers + Trainers + A Blazer


(Image credit: @emmarosestyle)

Style Notes: Emma always gets it right. This look is stylish, modern and yet so classic. Swap trainers for heels if you're heading on a night out. 

Shop the look:

8. A White Tee + Wide-Leg Jeans


(Image credit: @christietyler)

Style Notes: Wearing a white tee with jeans has never failed. While fitted silhouettes come and go, you just can't go wrong with wide-leg pants.

Shop the look:

9. A Denim Midi Skirt + Polo Knit


(Image credit: @meccajw)

Style Notes: The '70s inspiration can't be missed in this look, which is composed of more pieces I plan to wear for life. Who can say no to a knitted polo?

Shop the look:

Up Next: 10 Winter Outfits We're Already So Excited to Wear

This story was originally published on Who What Wear U.S. and has since been updated. 

Associate Editor

Sierra Mayhew was always destined to work in fashion, but she didn't know it at first. Growing up with no choice but to wear a rotation of school uniforms and activewear, her love for fashion really blossomed when she moved away for college and was able to finally define her very own personal style. Shortly thereafter, she interned at Elle magazine and instantly knew that editorial was for her. After graduating from the University of Notre Dame, she worked for ShopBazaar, contributing regularly to Bazaar.com, and finally made her way to Who What Wear, where she is an associate editor. When she’s not working, you can catch her always trying to catch a flight, rollerblading through New York City traffic, or exploring the latest luxury vintage boutique.