9 Anti-Trend Items Fashion Experts Are Wearing With Their Jeans This Year

There’s no doubt that jeans are a wardrobe staple most of us would be lost without. They provide the backbone to so many outfits, and they’re especially perfect for throwing on during this strange time when we’re in between seasons. As we inch our way out of summer and slowly approach the chillier days of early autumn, I know I'll find myself repeatedly reaching for denim to pair with everything from blazers and knits one minute to t-shirts the next.
Versatile is an understatement when it comes to jeans, and in theory, as well as being perfect for dressing down on relaxed weekends, they can easily be made to look really polished too. Whether you’re looking to dress them up for a date night or an important business meeting or you just like your denim to feel more elevated day to day, the key is to know what to pair them with, and fashion experts are, unsurprisingly, very good at it. To crack the code, I turned to my fellow industry insiders as well as influencers, and I’m here to report back on the most stylish and elevated jeans outfits I’ve seen.
It turns out there is actually a finite number of items fashion people repeatedly wear with jeans to make them look their best—nine to be precise. And the good news is they’re all really classic items you probably already own. Keep scrolling, and you’ll see the best classic items to wear with jeans that will always make your denim work harder, from chic blazers to oversized shirting, smart loafers to Breton stripes.
The 9 Best Classic Items to Wear With Jeans:
1. Relaxed Shirt
Style Notes: Not sure what to wear? The shirt-and-jeans formula works every single time.
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2. Blazer
Style Notes: Whatever colour or material you go for, rest assured a blazer will look chic with jeans. Add flats for a casual take or heels for a night out.
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3. Striped Jumper
Style Notes: Is there anything more perfect than blue denim and classic, Parisian stripes?
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4. Loafers
Style Notes: Oh loafers, you never steer me wrong. The perfect shoe for all seasons, wear it with any cut and colour denim and add a trench for rainy days.
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5. Trench Coat
Style Notes: This one needs no explanation. A great trench is such a wise investment and will be a staple in your wardrobe forever.
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6. Black Boots
Style Notes: Black, heeled ankle boots are an ideal accompaniment to blue, black or white denim. Choose a stiletto or block heel and you're set. Luckily, there are plenty of options on the high street as well as from our favourite designers this season.
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7. Leather Jacket
Style Notes: Leather in all forms works with denim. We're particularly fond of a trench, boxy jacket or blazer.
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8. Thin Knits
Style Notes: Not quite cold enough to bring out the chunky knits? Enter their thinner, lighter counterparts. A soft beige or grey hue is a chic choice.
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9. Strappy Heels
Style Notes: Jeans and heels is my go-to for an evening out. Keep the rest of your look casual or go all out with a statement top.
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Emily Dawes is an editor, stylist and writer with over 12 years in the industry. Known for impeccable taste, our readers trust her advice, especially in her column, expensive-looking high street buys. Working for Who What Wear UK since 2020, Emily has been a contributing editor, branded content editor and affiliate editor. Now, as senior shopping editor, she leads the e-commerce content strategy. After obtaining a BA in English and American Studies from Nottingham University, Emily landed at The Mail on Sunday’s YOU. As the magazine’s fashion editor, she travelled the globe to style and direct fashion editorials and celebrity cover shoots. As a freelancer, she has styled Grazia cover shoots, developed brand marketing and content plans and worked with VIP clients including Elizabeth Day.
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