If there's one thing I'm sure of this year, it's that I am obsessed with the celebrity style that has transpired in 2020—especially the shoes and handbags. There's newfound ease in the way celebrities are dressing and styling their looks, from menswear-inspired suiting paired with chunky sneakers to tailored wool coats with a voluminous clutch folded under the arm. This year, celebrity fashion is the epitome of effortless dressing, yet still being incredibly polished and on-trend.
And while you may be wondering what shoes and bags were worn in 2020, as most of this year was spent in the comfort of our home—where we replaced trendy heels with slippers and everyday ensembles morphed into pajamas—some fashionable pieces still emerged. The coolest shoe and handbag trends err on the side of comfort and functionality versus eye-catching and dramatic. Think sleek loafers and practical, easy-to-carry handbags. But don't worry—that doesn't mean they are boring. In fact, they are anything but. Keep scrolling to discover the coolest shoes and bags celebrities wore this season, hands down.
On Irina Shayk: Burberry Two-Tone Canvas and Leather Pocket Bag ($1190) and D-Ring Detail Leather Heeled Oxford Brogues ($900)
I have been living for Irina Shayk's lockdown style as the model and mother seems to step out in edgy, yet sophisticated looks. And to be honest, it's making me want to ditch the sweatpants and actually get dressed again. Though this outfit is more simple compared to her neon dress look, it's classic shoes and bags is what makes it so cool. Canvas bags with leather trim, like this Burberry number, definitely had a moment this year, and when styled with an oxford shoe, it becomes a mood.
On Joan Smalls: Ugg Marlene Sherpa Jacket ($128) and Classic Ultra Mini Boots ($140)
The year 2020 marks the return of mini Ugg boots, and I am all about it. Joan Smalls absolutely nails the look by styling them with a cozy jacket, contrasted with a body-hugging dress, and, of course, a small, structured clutch with a convenient strap to wrap around your wrist for a quick errand.
On Emily Ratajkowski: Inamorata Wilcox Button Up ($75); Dickies Crop Work Pants ($69); Hayward handbag; Nike Air Max 270 Sneakers ($609); Versace sunglasses
Let's be honest: Emily Ratajkowski can do no wrong in her outfits. Every look is better than the next, and so on. Embrace a colorful sneaker, like Ratajkowski, and style it a baggy cargo pant. Pair it with a ladylike, croc-embossed leather tote to complete the look.
On Rosie Huntington-Whiteley: Balmain blazer; Wardrobe.NYC Sweater ($450) and Leggings ($450); Aquazurra shoes; Balmain Medium 1945 Jacquard Shoulder Bag ($3400); Jessica McCormak jewelry
Rosie Huntington-Whiteley normalized dressing up again with this look. Breakout your favorite mesh, pointed-toe pump and baguette bag to casually fold under your arm, and you're officially ready to conquer the day.
On Bella Hadid: Coach x Jean-Michel Basquiat Coat; Chanel handbag; Prada Logo Plaque Chunky Heel Loafers ($850)
Another one of our go-to street style icons, Bella Hadid, has been serving us a lot of great looks this year. My personal favorite when it comes to shoes and bags is this look because of its subtle ode to '90s minimalist fashion. I remember when I got the knockoff version of this Chanel bag in the early 2000s and carried it practically everywhere.
On Katie Holmes: Bottega Veneta Padded Sandals ($880); Saint Laurent Tag Hobo Bag in Smooth Saddle Leather ($2550); Evolvetogether Mask
Embrace a pop of color by admiring Katie Holmes' yellow Bottega mules (and yes, these were the shoes of the summer this year) paired with a relaxed leather tote for a casual-cool look.
On Hailey Bieber: Magda Butrym blazer; Jacquemus Bralette ($150); Alexander Wang Bite Flip Embroidered Denim Shorts ($265); Bottega Veneta Exclusive Leather Beatle Boots ($1,150); Balenciaga Hourglass S Tote Bag ($1990)
No matter the circumstance, I can always count on Hailey Bieber to step out in a bold, and definitely inspiring, look. Case in point? This chunky platform boots + bright-red bag look.
On Jennifer Lopez: Brunello Cucinelli cardigan; Wolford Jamaika Bodysuit ($195); Dior bracelets; Balmain boots; Hermes handbag
J.Lo stepped out in the ultimate hybrid outfit; perfect for at-home and also incredibly chic for a quick errand. Next time you step out, try pairing your wide-leg lounge pants and cozy cardigan with a top-handle bag and combat boot to complete the look.
On Dua Lipa: Kids of Immigrants Sweatshirt ($90); Marc Jacobs Heaven Logo Baby Tee ($65); Bottega Veneta The Shoulder Pouch Bag ($2800); Prada Block Sneakers ($920)
A style icon I have absolutely fallen in love with this year, Dua Lipa, is always stepping out in unexpected pairing that just works. For instance, styling these chunky Prada sneakers with a slouchy, voluminous bag with classic jeans and a tee may seem odd, but it's actually super on-trend and easy to replicate.
On Hailey Bieber: Lemaire Single-Breasted Twill Overcoat ($1365); Alexander Wang Foundation Terry Hoodie ($225); Saint Laurent Skinny Jeans ($850); Aureum Collective Hoops ($188); Bottega Veneta The Pouch Bag ($2950); The Row Leather Ankle Boots ($1290)
Shoes and bags are often the moments in an outfit to really have fun and experiment with bold colors and prints. Hailey Bieber did just that by introducing an animal print clutch to her neutral look. Complete the look with a black modern, structured bootie to let the bag shine.
On Emily Ratajkowski: Aya Muse dress; Jennifer Miller Triple Strand Bracelet ($650); Stuart Weitzman Parton High Heel Boots ($795); Khaite Jeanne Small Leather Clutch ($1400)
Over-the-knee boots continued to have their moment this year—no matter the circumstance. Take a styling cue from Emily Ratajkowski and pair the boots with a monochromatic look and sleek, sophisticated handbag.
On Selena Gomez: Toteme suit; Puma sneakers; Cartier necklace
Though there is nothing new perse with a white sneaker, they continued to get a fresh update this year. From subtle design details like color paneling to a plethora of new silhouettes, the white sneaker remains a cool shoe to invest in this year. Selena Gomez keeps it simple by styling a white sneaker with a matching set for a more relaxed look.
Up next, discover the five leggings celebrities always buy for themselves, and you might too.
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J.Lo Just Debuted a New Way to Wear This "Boring" Blazer Trend That Feels So 2025BRB, adding one to my cart.
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Sorry to My Black Coats, But Chic Women in NYC Convinced Me to Prioritize This Color InsteadFrom Gisele to Katie.
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So Long, Classic Loafers—It Girls in Every Stylish City Are Wearing This Cool AlternativeDress like an in-the-know fashion girl.
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I Want a Rich-Looking Wardrobe—33 Perfect Picks From Nordstrom's (Early) Black Friday SaleGet a head start with these chic gems.
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Is It Just Me, or Is Every Stylish Woman in L.A. and NYC Wearing This Elegant Bag Color?Sorry, black bags.
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J.Lo Wore the Elegant Trend That Makes Every Outfit Look Like It Came From an Audrey Hepburn MovieFrom Charade to Breakfast at Tiffany's.
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Katie Holmes Wore the Pretty 2025 Color Trend Everyone Will Pair With JeansTake note.
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Fun Fact: The Absolute Best Designer Bags of the Season Are All From NordstromShop with ease, my friends.
