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

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(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.

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2. A Relaxed Blazer + Slip Dress

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(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. 

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3. A Cardigan + Straight-Leg Jeans

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(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.

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4. A Power Suit + Shoulder Bag

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(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.

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5. A Midi Dress + Boots + A Blazer

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(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. 

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6. A Striped Knit + Denim + Trench

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(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. 

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7. Tailored Trousers + Trainers + A Blazer

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(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. 

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8. A White Tee + Wide-Leg Jeans

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(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.

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9. A Denim Midi Skirt + Polo Knit

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(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?

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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. 

Sierra Mayhew
Fashion Editor

Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of experience in the fashion industry to the editorial team. Since joining Who What Wear in 2021, Sierra has made her mark by expertly blending luxury and accessible fashion content. Whether she's decoding the latest runway presentations or crafting a perfectly curated shopping list, Sierra's keen eye and relatable approach have solidified her as a trusted voice in the fashion space. She's also reported on major industry events like Paris Fashion Week and lent her expertise to red carpet coverage, ensuring her audience gets an insider's view of the most glamorous moments in style. Before joining Who What Wear, Sierra sharpened her skills at Harper's Bazaar and Elle, with bylines in Bazaar.com and collaborated with iconic brands such as Gucci and Ferragamo. Her ability to translate editorial expertise into viral social media content sets her apart, seamlessly bringing her articles and personality to life for a new generation of readers and followers. A graduate of the University of Notre Dame, Sierra brings a unique perspective to the fashion industry that is informed by her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.