Attending Anastasia Beverly Hills’ Raising Brows LIVE event in LA, Cindy Crawford wowed in a pair of plum, flared, tailored trousers. The sleek leg silhouette was fitted from hip to thigh, before flaring out at the knee, delivering a retro, party-ready feel.
A great replacement for those Christmas party dresses, a pair of tailored trousers and a dressed-up top are a versatile choice to head into the festive season with. From date night outfits to post-work celebrations, this combination is easy to reinvent and can often be taken from AM to PM with a few simple tweaks.
Despite its vintage-inspired silhouette, Cindy's look felt thoroughly directional, thanks to the deep plum hue, one of the biggest autumn/winter fashion colour trends for 2025. Pairing her trousers with the tonally matching Celeste top from A.L.C., the chic colour-drenched look was utterly seamless, elongating the supermodel's frame.
Get Cindy Crawford's Plum Party Look
Cindy's silk top features an asymmetric neckline and one shoulder detail. With sensational drape and handle, the scarf neckline taps into a silhouette trend we're seeing across coats and knits, too. Working with everything from denim to tailoring, or a silky slip skirt, this is a party-ready top you can rely on again and again.
The mid-rise waist of these tailored trousers makes them a great high-street alternative to Cindy's pair. To highlight your waist, tuck in draped tops to keep your shape, without losing any of that beautiful billowing shape. The figure-hugging thigh and kick flare leg echoes Cindy's look, and the deep plum shade is the perfect match.
These Mango heels are almost identical to the strappy, sandal-like shoes Cindy is wearing. With their intricate, barely-there design, they would play a supporting role to an outfit as a whole, without stealing the limelight, making them a solid wardrobe staple. The low-ish heel should mean that you can wear them with relative comfort all night long.
As this blouse is made from acetate satin and not 100% silk, you can get the luxe look of Cindy's A.L.C. top for a budget-friendly price. The similar silhouette emulates Cindy's top, but with a simpler silhouette. The draped fit, high neck, and scarf-style design deliver a high-end finish, and the berry-hued colouring catches the light beautifully.
A bootcut silhouette and leg-lengthening pleat details give these tailored trousers the same flared look as Cindy's. The burgundy tone emulates her style perfectly, and the deep colour is ideal for cooler climes. The high waist helps support and shape your middle, for a truly comfortable and stylish wear.
There's a good reason that these strappy, leather heels are a bestseller on the Revolve website. With a versatile, barely-there design, they effortlessly finish off any party look with ease and sophistication, with the ankle strap and short heel allowing for comfort as well as style. The slightly chunkier heel is ideal for those who need more support.
Completing her look with a pair of strappy heels, Cindy Crawford's red carpet ensemble was chic and understated. Keeping her jewellery equally minimal, the supermodel opted for small gold earrings and a gold watch, giving a nod to the quiet luxury aesthetic that favours pared-back elegance.
Tailoring has been a core autumn/winter fashion trend 2025, carried over from the previous season. While tailoring used to be reserved for our office attire, this sleek silhouette is now one that works from AM to PM, up-styled with luxurious fabrics and directional colour palettes for maximum versatility.
Skipping the seasonal wide-leg silhouette, we love Cindy's retro silhouette. The flared hem is balanced by her shoulder-baring top and higher neckline, which lengthens her frame and narrows her waistline. Paired with the plum hue, this is a great style to emulate as we head into party season.
