Ashlee Simpson’s Stylish Picnic Looks: Blazers, Bowler Hats, and Chic Denim

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In June 2011, celebrities gathered for the Elizabeth Glaser Pediatric AIDS Foundation’s annual “A Time for Heroes” picnic at the Wadsworth Theater Grounds in Brentwood, California.

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

Among them was Ashlee Simpson, who made good use of her time and celebrity status to help raise funds for the foundation to create a generation free of HIV.

Here’s Ashlee Simpson milling about at the picnic grounds on June 12, 2011.

Ashlee Simpson with her son Bronx Wentz at the Elizabeth Glaser Pediatric AIDS Foundation's "A Time for Heroes Event"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 Simpson gave the 7 For All Mankind black jeans she’s been wearing a lot lately a rest and traded them in for the James Jeans Twiggy leggings in slate.

Ashlee has also been spotted in these gray jeans before and has been seen alternating them with her favorite 7FAM black jeans.

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 hatAshlee 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)

Ashlee frequently wears these jeans and seems to favor pairing them with the same blazer and bowler hat she’s wearing in these pictures! Sometimes it’s just the hat, while at other times it’s just the blazer, but you get my point.

Maybe one of those jeans feels right when worn with a blazer/bowler hat for Ashlee? I know I have jeans that only look good with sure tops, shoes, and accessories. I’m betting that many of you have jeans like that, too.

Ashlee Simpson’s ensemble at the “A Time for Heroes” picnic, featuring a blazer and jeans, exemplifies a timeless fashion pairing embraced by many celebrities. For instance, Naomi Watts effortlessly combines sophistication and comfort by pairing a black structured blazer with distressed jeans, creating a chic twist on casual wear.

Similarly, Miranda Kerr showcases the versatility of this combination, often seen in denim ensembles that exude a polished vibe, even when incorporating heavily distressed jeans.

These instances highlight the enduring appeal of the jeans and blazer duo, inspiring those looking to emulate a stylish yet comfortable look. Here’s a closer look at Ashlee’s jeans:

James Jeans Twiggy Legging in SlateJames Jeans Twiggy Legging in Slate