Ashlee Simpson Elevates Her Petite Frame With Blazer, Bowler Hat, and Knee-High Boots

Long before street style blogs ruled social media, Ashlee Simpson was already making waves with her effortlessly edgy fashion.

At the 2011 “A Time for Heroes” charity picnic hosted by the Elizabeth Glaser Pediatric AIDS Foundation in Brentwood, California, she delivered a masterclass in casual-chic layering—bowler hat and all.

Although more than a decade has passed, this look still resonates with fans of tailored blazers, knee-high boots, and denim done right today.

Ashlee Simpson effortlessly combines a tailored black blazer with a chic bowler hat for a stylishly retro yet modern look (Credit: Adriana M. Barraza / WENN)

Ashlee Simpson used her platform to help raise awareness and funds for the foundation’s mission to create a generation free of HIV.

Photographed alongside her young son Bronx Wentz, Ashlee brought both star power and heartfelt presence to the family-friendly event, held on June 12, 2011, at the Wadsworth Theater Grounds.

Ashlee Simpson with her son Bronx Wentz at the Elizabeth Glaser Pediatric AIDS Foundation’s “A Time for Heroes Event” at Wadsworth Theater on the Veterans Administration Lawn in Los Angeles, California, June 12, 2011 (Credit: Adriana M. Barraza / WENN)

Ashlee Swaps Her Go-To 7FAM Jeans for Sleek James Twiggy Leggings

Ashlee Simpson gave her go-to 7 For All Mankind black jeans a break in favor of the sleek, slate-colored James Jeans Twiggy leggings — a slim-fit style that flatters her petite 5ft 4½ (163.8 cm) frame. She styled them with knee-high brown boots, which visually lengthened her legs and added a polished edge to her outfit.

A fan of both brands, Ashlee had been seen wearing these gray leggings on multiple occasions, often rotating them with her trusted black 7FAM jeans. The consistency in her denim choices highlights a signature off-duty formula: skinny jeans paired with tailored layers and standout footwear.

Ashlee Simpson stuns in a tailored black blazer, slate James Jeans Twiggy leggings, a casual graphic tee, knee-high brown boots, and a chic bowler hat (Credit: Adriana M. Barraza / WENN)

A Go-To Look: Ashlee’s Signature Blazer, Bowler Hat, and Jeans Combo

Ashlee often returns to these jeans, frequently styling them with the same black blazer and bowler hat seen in these photos. Sometimes she wears just the hat, other times just the blazer, but the overall pairing creates a signature look she clearly favors.

Like many of us, Ashlee likely has certain jeans that work best with specific tops, shoes, and accessories. Some outfits feel more balanced when certain pieces are worn together — a styling trick many fashion lovers can relate to.