For the longest time, the item that dominated my wardrobe was dresses. Being 5′ 3″ and a true hourglass shape, I always found it hard to find the right sort of trouser fit. Slim-fit styles would often pull across my tights while simultaneously gaping at the waist. Wide-leg styles would swamp me and be at least seven inches too long. This, however, I understand, as anyone taller needs the option of the length I can have a tailor trim off. Of course, this can be costly and, honestly, I simply became tried of trying styles on and inevitably having to return them. So, I temporarily gave up.
Still, I’m no quitter, and when trousers came back to the fashion fore in a big way a couple of years ago, I was hellbent on finding the pairs that worked for me. With more options on the market than ever and a honed focus on varied fit, surely now was my time to enjoy trousers in the way my friends and colleagues had done previously.
Now, I’m a bonafide trouser convert. Although dresses are still my favourite thing to wear, during the cooler months and day-to-day, I’ve come to rely on trousers as my uniform. My collection is still minimal and focuses on staple styles—black wide legs, beige crops, that sort of ilk—so, I decided to seek out some classic-trouser-outfit inspiration for the season ahead to help me keep my trouser looks feeling fresh but still totally timeless. After hours of searching for the chicest outfits Instagram has to offer, below, are 11 very elegant, totally classic trouser outfits I fully intend on re-creating this season. The best part is you should be able to do so too with pieces that are likely already in your wardrobe. Don’t say I’m not good to you.
11 CLASSIC TROUSER OUTFITS YOU’LL WEAR FOREVER
1. LEATHER JACKET + CREAM TROUSERS
Style Notes: I love an outfit with juxtaposition and here, the contrast between the fluid wide-leg trouser and the leather bomber just works.
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2. NEUTRAL KNITWEAR + CORDUROY TROUSERS
Style Notes: Corduroy trousers never go out of style, especially if you invest in them in timeless colourways. This brown pair looks perfectly pulled together with the addition of beige and tan tones.
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3. RELAXED BLAZER + WIDE-LEG TROUSERS
Style Notes: Blazers are the second-most worn item in my wardrobe, so it makes sense that I’d pair them with trousers. Doubling up on relaxed fits only adds to the effortless vibe of this outfit.
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4. TAILORED TROUSERS + TRAINERS
Style Notes: Whether you’re running errands or keeping your style low-key, the combination of trainers and tailoring never falters. Keep your sneaks chunky for even more 2024 appeal.
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5. RIBBED CARDIGAN + JEANS
Style Notes: I don’t know why but I’m always reluctant to include jeans in trouser edits but we can’t talk about trouser outfits without at least nodding to denim. While jeans are at the heart of many a classic outfit, you can always rely on a ribbed cardigan to give them an elevated flair. Shoes optional, depending on the time of year.
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6. TAILORED BLAZER + CROP TROUSERS
Style Notes: For a relaxed evening look, I always reach for, you guessed it, a blazer and trousers. This monochrome look is next on my list to re-create (ideally with the gorgeous Saint Laurent bag below).
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7. TWEED JACKET + CIGARETTE TROUSERS
Style Notes: We can’t talk classic outfits without sneaking in some tweed. Bouclé-style jackets always look elegant and pair perfectly with trousers—in fact, I’d say that’s what suits them best. I love this combination involving slim-leg, cigarette trousers; it feels so French!
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8. SLOUCHY CARDIGAN + WIDE-LEG TROUSERS
Style Notes: This is the sort of look I live in in the warmer months; simple, pull-on trousers, a slouchy cardigan, whatever jersey I have to hand and a basket bag. Fin.
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9. BLAZER + COTTON STRIPE TROUSERS
Style Notes: Cotton trousers are the lightweight wardrobe addition I now don’t know how I lived without. Blue-stripe pairs are a favourite amongst influencers who wear them nonstop during the summer months. Now, however, pair them with trainers and a blazer.
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10. CABLE-KNIT JUMPER + CARGO TROUSERS
Style Notes: I’ve said it a thousand times: One-colour outfits will always look supremely chic. This cargo-trouser and cream-knit pairing is one you can re-create at any price point and it’ll still look so premium.
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11. BLACK COAT + BROWN TROUSERS
Style Notes: Wearing black and brown together in one look used to be considered a fashion “sin”, but I think it looks high-end and stylish. For those who adhere to neutral palettes, this is the pairing for you.