Hailey Bieber’s Wide-Leg Trousers Prove Flip-Flops Are for Fall – Charm

August is usually peak shorts season among celebrities, before autumn’s trending pants take over in September. This month, however, a shorts shortage has swept the It girl nation. For every single pair of Daisy dukes, Hailey Bieber churns out five wide-leg trouser outfits, serving early-fall fashion inspiration weeks ahead of schedule.

On August 17, Bieber dined at Coucou Restaurant in West Hollywood wearing a khaki-colored take on the anti-trend. Her ’90s-inspired trousers were more high-rise than her usual pants, which she left belt-free. The elongated hems juxtaposed her fitted black long-sleeve top. Other angles reveal her shirt is a boat-neck basic, one of her favorite necklines this summer.

Bieber’s WeHo wardrobe would’ve leaned decidedly October-ish without her kitten heel flip-flops. The Rhode founder slipped on her trusty $520 Toteme thongs, which she’s worn on repeat since March. At this point, they’re the most versatile shoes in the supermodel’s closet, complementing jeans, capris, and trousers all season long. Knowing Bieber, the flip-flops will remain in rotation long after their (supposed) end-of-August expiration date.

Hailey Bieber was spotted post-dinner in fall’s wide-leg trouser trend.

(Image credit: Getty Images)

Bieber’s purse of the evening might’ve gone unnoticed by those who don’t study her daily style. But, after analyzing the blink-and-you’ll-miss-it bag, I can confirm: It’s the Small Park Tote Bag by The Row. The A-lister debuted her grained calfskin leather handbag this June. It immediately caught fashion girls’ attention for its flat handles, interior toggle closure, and $1,550 price tag.

Since June, she’s reworn it at least five times, including at the gym in late July. It looked surprisingly cool girl-coded alongside cloud-like slippers from her husband, Justin Bieber‘s streetwear label, SKYLRK.

The Row

Small Park Tote Bag in Leather

Since her trousers streak started in April, Bieber has favored wide-leg black pairs. (The lower the waistline, the better.) Until now, she had yet to style any other color.

In late June, she paired her now-signature Toteme sandals with similar-looking trousers, except in black. This time, her khaki pick was an unseasonal trench coat layered over a white crop top. Bieber’s belted Toteme bag bared a striking resemblance to her The Row tote.

Hailey Bieber styled the wide-leg trousers trend in late June 2025

In June, Hailey pulled off an unseasonal black pair.

(Image credit: Backgrid)

In late July, Marie Claire‘s associate commerce editor, Brooke Knappenberger, predicted the wide-leg trouser takeover, calling them the “best transitional piece out there.” Bieber is proving her point, one evening out at a time.