Denim cut-off shorts season is back, making it the perfect time to explore fresh ways to style this summer staple.
We’ve already featured other celebrities wearing it this year, such as Kendall Jenner, who gave it a retro flair, and Alessandra Ambrosio, who opted for chic styling.
Lucy Hale keeps it effortlessly cool in denim cut-off shorts, a retro ‘Farewell Tour 1982’ tee, and fringed ankle boots, adding a plaid shirt for a laid-back, stylish touch
This time, take style tips from Pretty Little Liars actress Lucy Hale. The actress stepped out for lunch with singer Joel Carouse, donning a casual ensemble of Urban Renewal turn-up hem denim shorts from Urban Outfitters paired with a graphic-printed shirt by Bandit Brand. The shirt appears to read “Farewell Tour 1982,” adding a touch of retro flair to her look.
Lucy, fresh off the release of her new song ‘Kiss Me,’ elevated her simple shorts-and-shirt combo by tying a plaid shirt around her waist. She gave it a bit of a boho vibe with fringed Louie ankle boots from Sam Edelman.
Lucy Hale and Joel Carouse enjoying a lunch date at Crave in Los Angeles on May 8, 2014 (Credit: WENN)
The denim cut-off shorts and tee look, worn with a plaid shirt around the waist, has been done countless times before.
Lucy’s accessories improved her outfit, balancing casual and chic elements. This ensured the outfit maintained a balanced look—not overly casual, bohemian, or 90s-inspired.
While Lucy Hale showcased a warm-weather take on denim cutoffs, Ashlee Simpson proved that this versatile staple can also be styled for cooler months—especially in LA’s mild winters.
Ashlee Simpson’s Winter Denim Guide: Rocking Shorts in LA’s Mild Winter
In December 2010, Ashlee Simpson wore her itty-bitty cutoff denim shorts even though it was winter. Of course, LA winters are mild, but Ashlee’s rocker-inspired look still offers cozy layering ideas.
Ashlee Simpson defies winter norms in LA, styling denim cut-off shorts with sheer black tights, lace-up oxfords, and a cozy plaid wool coat for a chic, edgy twist (Credit: The Media Circuit / WENN)
Ashlee Simpson’s usual rock’ n’ roll tee and ripped denim shorts get the cold treatment from a Topshop checkered wool cape and thick black tights.
Ashlee Simpson had her hair done at the Andy Lecompte Salon in West Hollywood, California, on December 10, 2010 (Credit: The Media Circuit / WENN)
Oversized sunnies remain a celebrity favorite, but swapping the high-end Fendi purse and classic lace-up oxfords for edgier, more rugged pieces adds a grungy touch.
Lastly, we added a lovely scarf and a cute hat to make things a little warmer and cozy.
Recreate Ashlee Simpson’s winter-ready denim look for a trendy, cozy style
While most wouldn’t consider denim shorts practical in 40-degree weather, Ashlee’s look makes perfect sense in LA’s mild winters, where temperatures average between 50 and 60 degrees Fahrenheit.
While Ashlee Simpson proved that denim shorts can work even in cooler weather, many celebrities continue to embrace this staple year-round, each bringing their own unique twist to the trend.
Stepping Out in Style: Celebrities Embracing Denim Shorts
Let’s explore how some of our favorite celebrities have styled this versatile piece, with a particular focus on their footwear choices:
Ashley Tisdale’s Casual Chic
- Outfit: Ashley Tisdale elevated a casual errand look by pairing Erin Wasson x RVCA Hish cut-off denim shorts with a plain grey t-shirt.
- Footwear: She complemented her ensemble with black booties, adding a touch of edge to her laid-back style.
- More Details: Ashley Tisdale’s Cut-Off Denim Shorts
Jessica Alba’s Relaxed Vibes
- Outfit: Jessica Alba kept it low-key in Fidelity Denim “Malibu” boyfriend shorts, a plain white tank top, and an Athena Procopiou cover-up.
- Footwear: She opted for white Birkenstock “Arizona” sandals, perfect for a relaxed day out.
- More Details: Jessica Alba’s Boyfriend Shorts
Selena Gomez’s Edgy Ensemble
- Outfit: Selena Gomez made a statement by pairing denim cut-offs with a Solid & Striped one-piece bathing suit and a B-Low the Belt “Bri Bri” belt.
- Footwear: She completed her look with Saint Laurent “Chelsea” boots, blending casual with chic.
- More Details: Selena Gomez’s Denim Cut-Offs
Kendall Jenner’s Bold Experiment
- Outfit: Kendall Jenner experimented with style by combining high-waisted shorts with a cropped tank top and an oversized black bomber jacket.
- Footwear: She added thigh-high Sophia Webster boots, showcasing a bold, fashion-forward look.
- More Details: Kendall Jenner’s Sexy Shorts
Chrissy Teigen’s Shopping Attire
- Outfit: Chrissy Teigen’s shopping attire consisted of One x Oneteaspoon “Bandits” shorts and a Janessa Leone “Stephen” fedora hat.
- Footwear: She paired her tiny shorts with brown 3.1 Phillip Lim “Ora” over-the-knee boots, adding a touch of sophistication.
- More Details: Chrissy Teigen’s Tiny Shorts
Vanessa Hudgens’ Boho-Chic Vibes
- Outfit: Vanessa Hudgens exuded boho-chic vibes in a Polo Ralph Lauren fringed suede jacket over a graphic tee and denim cutoff shorts.
- Footwear: She completed her look with black fringed ankle boots, embodying a free-spirited style.
- More Details: Vanessa Hudgens’ Boho-Chic Style
Alessandra Ambrosio’s High-Waisted Elegance
- Outfit: Alessandra Ambrosio wore high-waisted denim shorts paired with a loose gray sweater.
- Footwear: She chose light tan-colored ankle tie sandals, perfect for her activity-filled schedule.
- More Details: Alessandra Ambrosio’s High-Waisted Denim Shorts
Taylor Swift’s Casual Ensemble
- Outfit: Taylor Swift transformed the streets of New York City into her personal runway, effortlessly showcasing a simple white tank top and basic black shorts during her daily errands.
- Footwear: She accessorized her look with Rag & Bone Miles boots, adding a touch of sophistication to her casual ensemble.
- More Details: Taylor Swift’s Summer Ensemble
These stylish celebrities demonstrate the versatility of denim shorts, each adding their unique flair through thoughtful outfit and footwear choices.