Wiz Khalifa's Biggest Spending Weakness and a Deep Dive Into 10 Expensive Outfits He Wore

His fashion choices have become just as recognizable as his music. But while the rapper has built a reputation for wearing eye-catching designer pieces, he has also acknowledged that maintaining his wardrobe has come at a price.

Over the years, Wiz Khalifa has developed a distinctive sense of style that has become part of his public image. From designer labels to custom pieces, his outfits have often reflected his personal taste, and, as he later admitted, they have also become one of his biggest expenses.

His Biggest Spending Weakness

During a 2024 appearance on the "Sorry We're Stoned" podcast, hosted by mother-daughter duo Tish, 59, and Brandi, 39, Cyrus, Khalifa was asked what he was guilty of spending too much money on. "For me? Clothes," the rapper replied.

His answer surprised both hosts, who immediately reacted, "Really?!" After he confirmed it, the 39-year-old podcast host complimented his style, telling him, "When you walked in, I was like, 'That jacket...yes.'"

Her mother echoed the sentiment, describing the Pittsburgh native as "immaculate at all times." Khalifa jokingly revealed that his attention to detail was also the reason he arrived late for the podcast appearance, prompting laughter from both hosts.

The conversation then turned to how he puts together his looks. When asked whether he works with a stylist, the rapper revealed that he styles himself. His answer drew another surprised reaction from the hosts. "Are you freakin' kidding me?" one asked. "It's incredible," the other added.

A Closer Look at 10 of Wiz Khalifa's Expensive Outfits

Khalifa's appreciation for designer fashion has been evident in many of the outfits he has shared over the years. With clothing topping the list of his biggest spending regrets, here's a closer look at 10 of his looks, ranked from least to most expensive.

No. 10: A $11,450 Designer Look

Coming in at No. 10 is a look with a combined value of approximately $11,450.

The outfit paired several luxury pieces, including a Chrome Hearts Leather Space Patch cap priced at $1,285, Chrome Hearts Diamond Dog sunglasses worth $2,500, a Chrome Hearts Miami Exclusive Horseshoe T-shirt valued at $1,350, and a Chrome Hearts Black Leather Filigree belt priced at $4,600.

He completed the look with Balenciaga Distressed Baggy Shorts ($1,450), Chrome Hearts Green White Socks ($150), and Nike Air Force 1 '07 Low sneakers ($115).

No. 9: An $11,860 Designer Ensemble

Coming in at No. 9 is another look with a combined value of approximately $11,860.

The outfit featured a Chrome Hearts Leather Space Patch cap priced at $1,285, a Vetements Camouflage Reversible jacket worth $2,660, a Vetements No Social Media Couture T-shirt valued at $650, and a Chrome Hearts Green Belt priced at $2,400.

He paired the look with Balenciaga Ripped-detailing Denim jeans ($1,065) and Converse x Chrome Hearts Silver Sword Leather High sneakers ($3,800).

No. 8: A $15,605 Designer Outfit

Another outfit Khalifa shared carried a combined value of approximately $15,605.

The ensemble included a Chrome Hearts Red Leather Flame 6 Panel cap priced at $6,500, Chrome Hearts Roller White Sunglasses worth $2,400, a Chrome Hearts Horseshoe Long Sleeve shirt valued at $300, and a Chrome Hearts Black Leather Filigree belt priced at $4,600.

He completed the look with Balenciaga Blue Patched Pockets jeans ($1,690) and Nike Air Force 1 '07 Low sneakers ($115).

No. 7: A $16,110 Designer Outfit

One of Khalifa's pricier looks carried a combined value of approximately $16,110.

The outfit featured a Chrome Hearts Paris Trucker Cap priced at $600, Chrome Hearts BK-GP 50 Sunglasses worth $2,400, a Balenciaga Bomber Leather Jacket valued at $8,790, a Chrome Hearts Collar Logo Black Long Sleeve shirt priced at $550, and a Celine Logo Embroidered White T-shirt worth $590.

He rounded out the ensemble with a B.B. Simon Adabelle Western Black belt ($395), Balenciaga Blue Destroyed Super Faded jeans ($1,550), and Rick Owens Geobasket High-top sneakers ($1,235).

No. 6: A $16,840 Designer Outfit

Another of Khalifa's luxury outfits featured pieces with a combined value of approximately $16,840.

The look included a Chrome Hearts Leather Blue Flame Cap priced at $5,500, Chrome Hearts Roller Star Black Sunglasses worth $2,600, a Rick Owens Level T T-shirt in White valued at $425, and a Chrome Hearts Black Leather Filigree belt priced at $4,600.

He finished the ensemble with Chrome Hearts Light Wash Denim Carpenter shorts ($3,600) and Nike Air Force 1 '07 Low sneakers ($115).

No. 5: A $16,960 Designer Outfit

This designer look carried a combined value of approximately $16,960.

The outfit featured Balenciaga Silver Skin Xxl Cat Sunglasses priced at $630, a Balenciaga Black Hooded Leather Jacket worth $8,250, a Balenciaga Black Darkwave Logo hoodie valued at $3,350, and a Balenciaga Grey Skater Oversized T-shirt priced at $1,350.

Khalifa paired the ensemble with Balenciaga Bi-Material Cargo Pants ($2,505) and Balenciaga x Crocs Black Faux Fur Mules ($875).

No. 4: A $17,345 Designer Outfit

Another standout look from Khalifa's wardrobe carried a combined value of approximately $17,345.

The outfit included a Balenciaga BB Sprayed Cap in Grey priced at $495, Chrome Hearts Girth Quake Sunglasses worth $2,700, a Miu Miu Logo-embroidery Bomber Jacket valued at $4,000, and a Chrome Hearts Black Leather Filigree belt priced at $4,600.

He completed the ensemble with Balenciaga Graffiti Baggy Pants ($1,750) and Converse x Chrome Hearts Silver Sword Leather High sneakers ($3,800).

No. 3: An $18,009 Designer Outfit

Khalifa also put together an outfit with a combined value of approximately $18,009.

The look featured Chrome Hearts Spreader Glasses Trans sunglasses priced at $1,709, a Chrome Hearts Leather Bomber jacket worth $10,000, and a Chrome Hearts Roller Belt valued at $2,500.

He completed the ensemble with Converse x Chrome Hearts Silver Sword Leather High sneakers ($3,800).

No. 2: An $18,735 Designer Outfit

Among Khalifa's most expensive ensembles was a look valued at approximately $18,735.

The outfit featured a Chrome Hearts Leather Blue Flame Cap priced at $5,500, Chrome Hearts Roller Star Black Sunglasses worth $2,600, a Chrome Hearts Black Blue Long Sleeve shirt valued at $545, and a Chrome Hearts Black Leather Filigree belt priced at $4,600.

He completed the look with Chrome Hearts Leather Double Knee shorts ($4,320), Chrome Hearts x Foti Black Socks ($150), and Rick Owens Geobasket Black sneakers ($1,020).

No. 1: A $23,730 Designer Outfit

Topping the list was Khalifa's most expensive outfit, with a combined value of approximately $23,730.

The ensemble featured Chrome Hearts Roller Star Black Sunglasses priced at $2,600, a Chrome Hearts Leather Bomber jacket worth $10,000, a Chrome Hearts White Thermal Top valued at $650, and a Chrome Hearts Roller Belt priced at $2,500.

He finished the look with Chrome Hearts Double Knee Pants ($6,000), Rick Owens Geobasket Black sneakers ($1,020), and a Louis Vuitton Brown Monogram Toiletry bag ($960).

While Wiz Khalifa admitted that clothes remain his biggest spending weakness, his wardrobe also reflects the personal style that has become synonymous with his public image.

From luxury pieces by Chrome Hearts and Balenciaga to designer collaborations and accessories, the rapper has assembled a collection of outfits carrying five-figure price tags.