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From layering to mixing materials.
Iconic as Princess Diana’s style was as a whole, it’s her looks for the colder seasons that deserve special attention. Perhaps it’s her innate knack for layering or her simple love of a great oversized blazer or pair of high-waisted jeans, but Lady Di had cold weather dressing down to a science.
Whether she was wearing a black-tie dress and statement jewelry or sticking to her uniform of casual and tailored everyday wear, Princess Diana’s style never missed the mark — and it still inspires today. Moreover, with the resurgence of ’90s trends in every stylish girl’s closet these days, Lady Di’s style legacy is gaining more and more influence by the day.
So, now that the weather is starting to turn and your wardrobe is in dire need of a little bit of a seasonally appropriate makeover, might we suggest looking to one of the most iconic style mavens of this century?
Ahead, take a peek at Princess Diana’s best winter looks and shop them out for yourself. Your wardrobe will thank you.
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Princess Diana’s Canadian Tuxedo Look
Upgrade your Canadian tuxedo game with a contrasting material, à la Princess Diana’s oversized leather bomber jacket.
Princess Diana’s Canadian Tuxedo Look
No matter the season, consider a lighter wash to brighten up your head-to-toe denim look.
Princess Diana’s Canadian Tuxedo Look
Go for an easy fit, but not oversized, when it comes to finding the perfect pair of mom jeans.
Princess Diana’s Canadian Tuxedo Look
If you want to fully channel Lady Di, consider a leather jacket with an oversized bomber shape to wear on top of your denim-on-denim ensemble.
Princess Diana’s Little Black Dress
For a look that works for work, parties, and everything in between, upgrade your go-anywhere little black dress with a longline blazer in a bright shade of blue.
Princess Diana’s Little Black Dress
Keep it easy with a throw-on-and-go black dress that you can wear morning, noon, or night.
Princess Diana’s Little Black Dress
Brighten up your LBD with a bright blue blazer that’s longline in shape to mix up your proportions.
Princess Diana’s Layered Outfits
Princess Diana layered like a pro, mixing tailored basics, like a blazer and leather boots, with off-duty favorites like a sweatshirt and blue jeans.
Princess Diana’s Layered Outfits
Keep it cozy with a bright white sweatshirt, whether you’re styling it with the matching pants for at-home wear or switching it up with denim like Diana herself.
Princess Diana’s Layered Outfits
Top your sweatshirt with a tailored blazer, taking a cue from Princess Diana’s book, giving a more sophisticated appeal to your cosy athleisure top.
Princess Diana’s Layered Outfits
The only thing left? A pair of stylish jeans that are high waisted, straight legged, and vintage-inspired.
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