As I write these, it’s been 595 weeks, three days, four hours, and 23 … 24 minutes since the last “The Oprah Winfrey Show” aired on television but who’s counting? The one-time news anchor turned talk show host turned lifestyle guru’s popularity has not diminished despite not being on air for more than a decade. That’s thanks in part to her continued roles in movies, high-profile interviews, and a magazine that touts everything from her “favorite things” to articles on everything from fashion to social issues.
It’s that fashion angle, combined with “Oprah’s favorite things” that brings us to our list today. Because, let’s be honest, Oprah has always managed to look comfortable and effortlessly chic at the same time, and I have to think it’s because she’s a woman who knows what she likes and what works for her. What you’ll find below is “Oprah-inspired,” shall we say, based on the types of styles she’s seen in — comfy two-piece outfits, chic loungewear, oversized bags, fuss-free shoes and, of course, classic shades.
You will love our editor’s curated product picks! FYI: We are an Amazon affiliate partner and may get a share of the sale of your purchase (at no cost to you).
Black Like My Heart
I’m going to let you in on a little secret: Solid-colored outfits are slimming but it doesn’t really matter what color you choose. For me (and Oprah, apparently), it’s all black everything, just like my heart. This two-piece tracksuit is easy weekend dressing defined and can be dressed up or down depending on the event (and your mood). It comes in six colors and sizes up to XXL.
Just Lounging Around
There are very few things I love more than loungewear and conveniently enough, most things can be done while wearing loungewear. This loungewear set is soft and fuzzy and probably the outfit you’re going to want to live in this winter. Choose from several colors including the most delicious army green. Reviewers rave about how soft and comfortable this set is.
Hit ‘Em With A Two-Piece
I’m not quitting on the two-piece outfits just yet because this lightweight set was worth the add for less than $37. Made from soft, skin-friendly wool, this outfit has long raglan sleeves and a body long enough to cover the booty as well as loose-fitting pants with an elastic waist. Choose from eight color options in the pants variety or hide away shorts set for warmer days.
On Cloud Nine
If these slides look like you’d be walking on a cloud, there’s a good reason: They’re affectionately dubbed cloud slippers and walking on these bad boys is like tiptoeing on the fluffiest surface ever invented. (That’s thanks to the incredibly thick sole.) These come in 16 different colors (with one adorable animal print) and a wide range of sizes. They’re priced right, too, at just $20.
If The Shoe Fits
Celebrities might never admit it but they want to be comfortable just like we do. And, they dress down plenty, which makes simple tennis shoes a hot commodity. This version has a pre-distressed upper, cute detailing on the back, and a zipper that doesn’t do anything but look adorable. This brand has great reviews and the product itself can be purchased with the “Prime Try Before You Buy” program.
It’s In The Bag
It’s hard to pin a particular style of purse on any given celebrity since they change up their look so often. This medium hobo bag comes in more than a dozen colors, has three interior compartments, and is made from lightweight faux leather. Reviewers love its simple design and that it looks like a more expensive bag despite its $33 price tag.
I Need Structure
There are times the situation calls for a more structured bag and this $42 option is worth a look. These bags have four pockets (some zippered, some not), handles, a shoulder strap, and gold hardware. I love reviews like this one: “I cannot express how much I love this purse. I got the one in pink and it’s now my new favorite.”
I don’t know where you live and it doesn’t matter because it’s booties season and yes, that applies to you, too. This high-top, slip-on version has a non-slip soul and elastic panels on the side to make it easier to slip on and off. Choose from four solids and the adorable cheetah print pictured above. These are the perfect finish for jeans, leggings, and more this fall and beyond.
Baby, You’re A Star
Have you seen the cost of Golden Goose sneakers? Holy price tag, Batman. These shoes are a pretty close representation that won’t require you to take out a second mortgage on your house. They come in several designs, each with the usual stars on the side, and don’t have that “I walked 10 miles in the mud in these, can’t you tell?” look that authentic Golden Goose sneakers have. But, hey, if you’re into that, no judgement here.
It’s In My Jeans
Everybody needs at least one good pair of jeans in their closet … Oprah included. While I’m pretty sure she’s not wearing a $45 pair from Amazon, that’s her loss and your gain. These jeans are plenty stretchy with just enough distressing to look lived-in. And, the hem is perfect for everything from tennis shoes to heels. Choose from lots of different wash options.
I absolutely refuse to spend top dollar on sunglasses because I inevitably lose or damage them. These shades are on trend and priced right at less than $15. The round styling and tortoise design are super chic and the lenses are polarized, making this a purchase that looks a lot more expensive than it actually was. The clear frames with pink lenses are worth another look.
Hip To Be Square
Every woman deserves an oversized pair of sunglasses that she can sit behind at brunch and silently judge people while wearing. These $14 shades are that pair. One reviewer said, “I love the look of these sunglasses. They’re cute and trendy, and definitely a great deal.” There are lots of options here, too, including white and pink and a black gradient with a leopard frame.
This is singlehandedly one of my favorite purchases on Amazon of all time and it’s just as chic and adorable as the picture shows. I have this in two colors — green and khaki — and it’s the perfect sweater for cooler days paired with leggings. (I legit just added this orange to my cart so it’ll be coming home to me soon!)
Scarves are the perfect seasonal wardrobe piece because they can double as a coat (when it’s not freezing) or be used to jazz up a sweater or jacket. This scarf is done in shades of pink, cream, and green, which is surprisingly chic. You can even use this as a wrap or shawl. It offers a lot of versatility for just $12.
Oprah and I have a lot in common. She loves shoes … I love shoes … yeah, that’s probably about the extent of it but that’s enough. These slip-on flats come in a ton of colors and are uber comfortable, according to the reviews. One shopper said, “best shoes I’ve probably ever bought for work.” Snag these for $36 and then go back for more.
Dress To Impress
Sometimes dresses just don’t feel complete. I don’t really know why but some seem like they’re missing “something.” This sweater dress is not one of those with a chic wrap styling, a pleated skirt, and an adorable tie at the waist. The midi length is totally in style right now, too. Pair it with your favorite flats or heels for holiday parties around the corner.
Jog(ger) Your Memory
I’ve grown to love the pervasive jogger. They’re every bit as comfortable as leggings (stay with me here) but look more pulled together thanks to the structured style with banded ankles. These joggers come in nearly 25 color options, which means if you buy them all, you won’t need any other clothing. Except for probably a shirt. Yeah, please wear a shirt. Don’t make it weird.
Your Fuzzy Favorite
This product page had me at “sherpa-lined sweatpants” because, um, fall and winter and stuff. There are a dozen colors to choose from here and they’re “super soft and thick,” according to one review I checked out. The perfect combination of comfort, function, and fashion, you could totally run in Walmart in these relaxed-fit pants or you could stay right on your couch 24/7.
A Soft Touch
We’ve talked cozy bottoms so now it’s time to talk about a cozy top and I seriously want to wear this open-front cozy jacket with all the things. Can’t you just imagine reaching through your screen and touching that fuzzy softness? This jacket has an oversized hood and handy pockets. It’s all about the pocket, amirite? Buy this now for less than $40 and look cute all season long.
Blaze-r A Trail
Oprah is the master of the casual blazer, which is all I’ll wear too because I honestly find them tight and restricting. This jacket has an oversized fit, front pockets, a lapel, and a single button that can be closed (or not). Pair it with slacks for a day at the office or throw it on over jeans and a graphic tee for the perfect night out look.
Jump(suit) For Joy
There’s nothing simpler to throw on than a jumpsuit … unless and until you need to pee but we’re not going to discuss that. A one-piece design, this fabric is soft, stretchy, flowy, and lightweight but not see-through. (It would look adorable paired with that blazer just above.) The pants are a wide-leg styling, which flatters all body types. Dress it up or down.
Cooler days are ahead and even those of us who hate coats are going to need a good one This one is from Amazon Essentials and checks a lot of boxes: Lightweight, hooded and water-resistant. I love the slightly longer length on this puffer coat, too, so there aren’t any cold-blast surprises sneaking in at your waistline.