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

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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 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)

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"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 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)

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.

🎩 Celebrities Rocking Bowler Hats With Hot Shoes:

Celebrity Style Inspiration: Blazers and Jeans as a Timeless Fashion Duo

Ashlee Simpson’s ensemble at the “A Time for Heroes” picnic, featuring a blazer and jeans, exemplifies a timeless fashion pairing that many celebrities have embraced. 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 combination, inspiring those seeking a stylish yet comfortable look. Here’s a closer look at Ashlee’s jeans:

James Jeans Twiggy Legging in SlateJames Jeans Twiggy Leggings in Slate

Stepping Out in Style: Ashlee Simpson’s Most Memorable Shoe Moments

Ashlee Simpson has consistently showcased her unique fashion sense through her choice of footwear. From red carpet events to casual outings, here are some of her most notable shoe moments:

Disco Glam at the 2017 American Music Awards

  • Event: 2017 American Music Awards
  • Outfit: Ashlee dazzled in a Christian Siriano ombré sequin gown.
  • Footwear: She completed her look with Giuseppe Zanotti heels, adding a touch of elegance to her ensemble.
  • Read more: Ashlee Simpson’s disco-chic look at the 2017 AMAs

Boho-Chic Vibes at the ‘God vs. Trump’ Premiere

  • Event: ‘God vs. Trump: Only Love Wins’ Premiere
  • Outfit: Ashlee wore a black sheer duster paired with an embroidered vintage purse.
  • Footwear: She opted for Alaïa cutout sandals, showcasing her flair for statement footwear.
  • Discover more: Ashlee Simpson’s boho-chic ensemble at the premiere

Effortless Winter Chic at LAX

  • Event: Travel outfit at Los Angeles International Airport
  • Outfit: Ashlee sported a red striped coat over skinny jeans, accessorized with a fedora hat and oversized sunglasses.
  • Footwear: She chose Golden Goose leopard suede slide sneakers for a comfortable yet stylish look.

Ashlee Simpson at the airport, wearing a red striped coat, skinny jeans, leopard print sneakers, oversized sunglasses, and a fedora hatAshlee Simpson at the airport, sporting a red striped coat, skinny jeans, oversized sunglasses, a fedora hat, and Golden Goose leopard print sneakers (Credit: WENN)

Edgy Maternity Style in AllSaints Boots

  • Event: Christmas shopping in Beverly Hills
  • Outfit: Ashlee embraced an all-black ensemble featuring skinny jeans, a sweater, and a fur coat.
  • Footwear: She elevated her look with AllSaints ‘Widow’ boots, demonstrating her edgy maternity style.
  • Explore her style: Ashlee Simpson’s edgy maternity fashion with AllSaints boots

Casual Chic with Chanel Graffiti Bag

  • Event: Family outing in Los Angeles
  • Outfit: Ashlee kept it casual with a laid-back ensemble, letting her accessories shine.
  • Footwear: While her shoes were understated, her limited edition Chanel Graffiti Messenger bag stole the spotlight.
  • More details: Ashlee Simpson’s standout accessory: the Chanel Graffiti bag

These moments highlight Ashlee Simpson’s ability to blend comfort with style, making her a true fashion icon.