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
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
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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We will never stop shouting about Arket's blazer. Some of the best we've ever tried on, they fit well, are good quality and are more affordable than other styles.
3. A Cardigan + Straight-Leg Jeans
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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& Other Stories denim is so good. I love the wash and fit of the Favourite Cut Jeans.
4. A Power Suit + Shoulder Bag
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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Go bold and match the blazer with the trousers for a real style moment.
5. A Midi Dress + Boots + A Blazer
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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Erdem is my go-to brand for pretty midi dresses that I'll pull out season after season. This style will look just as good with boots as it will with sandals.
Not yet discovered NA-KD? It's a great source of affordable, trend-led clothing.
Cowboy boots are having a moment. This tan pair puts a timeless twist on the trend.
6. A Striped Knit + Denim + Trench
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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& Other Stories has plenty of striped jumpers on site now, but this is one of my favourites.
I live in these jeans. Dress them up with heels and a fun top or down with trainers and a sweatshirts.
7. Tailored Trousers + Trainers + A Blazer
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
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
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 is a fashion editor at Who What Wear, bringing a decade of industry experience to the editorial team. Since joining in 2021, she has made her mark by blending luxury and accessible fashion, decoding runway trends, and curating must-have shopping lists. 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. A graduate of the University of Notre Dame, Sierra translates editorial expertise into viral social content, making fashion engaging for a new generation. Her unique perspective is rooted in her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.
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