Star Style Meets Real Life: How to Copy Oprah’s Chic Denim Look

Affordable picks capture the spirit of her fashion-forward jacket, bag and heels

4-minute read

Oprah Winfrey wearing an all denim outfit, with labels explaining each part of the outfit.
Let us show you how to make Oprah Winfrey's "Canadian tuxedo" look your own.
AARP (Getty Images, 2)

Key takeaways

  • Oprah Winfrey’s designer double-denim outfit uses matching pieces to create a polished, slimming look.
  • A feminine denim jacket, bootcut jeans, statement earrings, a satchel and heels recreate the style for less.
  • Low kitten heels deliver the same dressy effect as stilettos while being easier to wear.

Do you want to dress like a celebrity?

Stars glammed up in red-carpet gowns are fun to see, but what women over 50 really love best are the outfits celebrities choose for daily real life. What does it take to replicate those looks for yourself? This is the first column in a series that gives readers a dress-like-a-star guide.

More Ways to Benefit

The star

Oprah Winfrey 

The outfit

Chloé puff-shoulder, chain- and charm-adorned denim jacket ($2,250); Chloé bootcut split-hem jeans ($1,290); Chloé small Paddington bag ($2,450); dark heels; statement pearl earrings.  

The total look

Wearing double denim, top and bottom, is what style observers call a “Canadian tuxedo.” Think of it as a casual suit. The usual duo pairs basic jeans with a denim trucker jacket, but Oprah’s version is A-list designer, super sophisticated and glitzed up with high heels, statement earrings and a fancy bag. Apart from the obvious fashion-worthy benefit, the matchy-matchy top and bottom are an effective dress-slim, monochromatic strategy. 

Get the look for real life: 5 things you need

Three different styles of denim jackets.
(From left) H&M Puff-Sleeved Twill Jacket in Denim Blue; Cinq a Sept Women’s Lyla Denim Shirt Jacket in Light Wash; Anna-Kaci Women’s Ruffle Trim Denim Jacket Long Sleeve Button Front Jean Blazer with Collared Neck in Blue.
AARP (H&M, Bloomingdale’s, Target)

1. A glam denim jacket

Oprah’s denim jacket is all about feminine details and a stylish twist. You won’t find an exact low-cost dupe, but dressed-to-frill styles such as the Anna-Kaci Women’s Ruffle-Trim Denim Jacket, Long-Sleeve Button-Front Jean Blazer With Collared Neck in Blue ($59, target.com), a hip-covering romantic topper; the H&M Puff-Sleeved Twill Jacket in Denim Blue ($48, hm.com), with a stand-up collar and shirring; and the Cinq à Sept Women’s Lyla Denim Shirt Jacket in Light Wash ($207, bloomingdales.com), another puff-sleeve, shirred version, are equally eye-catching. My tip: Choose a jacket in a medium-blue wash to make it easy to pair with the jeans you wear year-round.

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Two different styles of bootcut jeans.
AARP (Kohl’s, Quince)
(From left) Levi’s Women’s Classic Bootcut Jeans in Camp Denim; Quince Women Luna Stretch Flare Jeans in Seaside Blue.

2. Curve-conscious bootcut jeans

Oprah’s five-pocket bootcut designer jeans are a bust- and hip-balancing style that flatters all. You want a true bootcut, or even a mini bootcut, rather than a more extreme flare. (Some jeans labeled “flare” are really bootcut!) Choose a medium- or high-rise style — whichever suits your bust and proportions — and a clean bottom hem rather than a frayed one to keep the look classy. Good choices include Levi’s Women’s Classic Bootcut Jeans in Camp Denim, Lapis Awe or Lapis Wave ($65, kohls.com), a mid-rise; Quince Women Luna Stretch Flare Jeans in Seaside Blue ($50, quince.com), a mid-rise that comes in short, regular and long lengths; and Wit & Wisdom Madison High-Waist Bootcut Jeans in Mid Blue Artisanal ($88, nordstrom.com), in regular or petite.

A pair of pear and gold drop earrings.
A New Day Pearl and Crystal Linear Drop Earrings in Gold/Pearl
Target

3. Statement earrings

You could wear hoops or sparkling earrings, but head-turning pearls amp up the chic denim effect and bring a glow to your face. Oprah’s oversized drops make the point, as do lightweight danglers like A New Day Pearl and Crystal Linear Drop Earrings in Gold/Pearl ($13, target.com); extravagant drop hoops like the Freya Rose Seed and Baroque Pearl Mid Hoops in Gold ($265, nordstrom.com); and jumbo drops like the Baublebar Elizabeth Pear Earrings ($48, baublebar.com).

Two different satchel style handbags.
(From left) BCBGeneration Triple Compartment Satchel With Lock & Charm in Wine; Michael Michael Kors Women’s Hamilton Extra Small Satchel Handbag in Black.
AARP (Kohl’s, Macy’s)

4. A sassy boho satchel

Satchel bags are back, and Oprah clearly knows the Chloé version is a “cool-girl” look for the over-50 crowd. However, you can find much more affordable look-alikes with gold hardware and padlocks. My advice? Avoid styles whose handles are too small to sling over a shoulder. Instead, choose versatile satchels that can go from hand to shoulder or that have an optional crossbody strap, like the Michael Michael Kors Women’s Hamilton Extra Small Satchel Handbag in Black, Olive or Luggage ($180, macys.com); the BCBGeneration Triple-Compartment Satchel With Lock and Charm in Wine or Black ($49, kohls.com); or the Karl Lagerfeld Paris Maelynn Satchel in Black or White Pepper ($378, nordstrom.com), in any neutral you love. You can match heels and bag, or not — both ways look great.

Two different styles of slingback kitten heel pumps.
(From left) Cushionaire Women’s Saby Slingback Kitten Heels in Black Smooth; Naturalizer Women’s Tansy Snip Toe Dress Slingback Pumps in Black Faux Leather; Sam Edelman Women’s Bianka Slingback Kitten Heels in Black Leather.
AARP (Target, Macy’s, Bloomingdale’s)

5. Posh heels

Heels are the bottom line for Oprah — no sneakers, flats or loafers. Of course, pointy-toed heels are a celebrity/royalty thing, but would you wear them? Most women over 50 would rather get a root canal than wear high heels again. Sorry, Oprah, but we’re not jumping from limo to door, and low leather kitten heels with a 2- to 2.5-inch height offer the same sexy look in a more walkable style. A narrow heel (instead of a chunky block heel) and a soft-point almond toe are what make the look work.

Try a pair of very “in” black slingbacks with cushy padded insoles, like the Cushionaire Women’s Saby Slingback Kitten Heels in Black Smooth ($70, target.com); the Naturalizer Women’s Tansy Snip-Toe Dress Slingback Pumps in Black Faux Leather ($115, macys.com); the Cole Haan Women’s Tyldie Kitten-Heel Slingback Pump in Black Suede ($110, nordstrom.com); or Clark’s Women’s Kepley Lane Slingbacks in Black Leather ($70, zappos.com), all in sync with the outfit’s trendy look. Prefer a closed-toe pump? Slip on the Trotters Women’s Kimber Pump in Black ($125, dsw.com), a kitten heel with a higher vamp (a.k.a. the part that covers the toes) and plenty of modern attitude.

The key takeaways were created with the assistance of generative AI. An AARP editor reviewed and refined the content for accuracy and clarity.

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