Sydney Sweeney has been everywhere promoting Christy while dealing with the conversation around her American Eagle campaign. With so many eyes on her, the wardrobe choices became part of the story. Across morning shows, late-night and street style moments, we saw sweet, experimental and occasionally confusing looks in quick rotation.

Sydney Sweeney, Gianni Versace 1996, Good Morning America, New York street style, celebrity daywear, vintage Versace, Manolo Blahnik Maysale pumps, Jimmy Choo Bar bagTheStewartofNY/GC Images

Good Morning America Arrival

Sydney opened her day in a 1996 Gianni Versace cream suit, complete with a pleated mini skirt and a rounded collar jacket. It carried that polished morning-show friendliness, but some might feel that this is slightly too prim for her. Paired with Manolo Blahnik Maysale pumps and a Jimmy Choo Bar Hobo bag, the look tipped fully into “White House East Wing intern,” but I don’t hate it. It felt like a welcome reset.

Sydney Sweeney, Sportmax Spring 2026, New York street style, beige leather jacket dress, leather boots, Miu Miu Mini Aventure bag, celebrity daytime styleXNY/Star Max/GC Images

Good Morning America Departure

Then came the switch-up. The Sportmax Spring 2026 leather jacket repurposed as a mini dress was far more aligned with Sydney’s confident approach to dressing. It’s undeniably bold for November, but I appreciated the styling choice not to pair it with the runway’s wide trousers which would have overwhelmed her. Beige leather boots and the Miu Miu Mini Aventure bag kept the look cohesive. This was the point in the day where she found the rhythm. Oh so I thought.

Sportmax Spring 2026

Sydney Sweeney, Markgong Spring 2025, trench coat-inspired look, daytime TV style, Manu Atelier Le Cambon 25 bag, Prada sunglasses, celebrity talk show appearanceTheStewartofNY/GC Images

The Drew Barrymore Show

The Markgong Spring 2025 trench-inspired jacket and matching dress overwhelmed her entirely. The idea is interesting — sculptural tailoring meets classic trench coat codes — but the proportions swallowed her frame. Even with the black Manu Atelier Le Cambon 25 bag, boots and Prada shades lending some severity, the look felt unresolved.

Markgong Spring 2025

Sydney Sweeney, Patou Fall 2025, brown coat look, New York street style, celebrity press tour fashion, tonal dressing Aeon/GC Images

The Late Show with Stephen Colbert Arrival

This Patou Fall 2025 look left me scratching my head. It looks super chic on the runway, but on Sydney, my first thought was that it read far older on her. In reality, this might come down to the styling and perhaps the fact that this deep shade of plum doesn’t really suit her.

Patou Fall 2025

Sydney Sweeney, Magda Butrym black asymmetric corset mini dress, Paris Texas Lidia Slingback pumps, Gucci sunglasses, late-night show style, black tights styling TheStewartofNY/GC Images

The Late Show with Stephen Colbert Taping

Here’s the win of the tour. The black Magda Butrym asymmetric corset mini dress delivered the kind of confident glamour she wears best. Paired with sheer black tights, Gucci sunglasses, and Paris Texas Lidia slingback pumps, it gave the right structure without forcing a theme. It was sexy without being heavy-handed. This is what most of us have been wanting from her.

Sydney Sweeney, Brunello Cucinelli Fall 2025, shearling vest, corduroy Bermuda shorts, croc embossed boots, layered textures, New York night styleAeon/GC Images

Final Look

The Brunello Cucinelli Fall 2025 mix — shearling vest, silk shirt, corduroy Bermuda shorts, croc-effect boots and leather belt — had interesting pieces, but they didn’t harmonise. It felt more like a styling exercise than a look. Edited, this could have been rich, autumnal, and easy. As is, it comes across as overworked.

Stylist: Molly Dickson.

Brunello Cucinelli Fall 2025

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