I’m Planning Ahead—These 6 Chic Bags Would Make the Perfect Gift this Holiday Season
I wouldn’t be complaining if they showed up on my doorstep.


When the holidays roll around, my mind always wanders to the same place: this year’s designer It bag. While everyone else is making wish lists filled with practical things, I’m picturing myself untying a silky ribbon to reveal the handbag of the season—something timeless yet fresh, that everyone wants their hands on. It’s become a bit of a personal tradition: as soon as the temperatures drop, I start mentally bookmarking the bags that I’d love to see with my name on the gift tag. A girl can dream, right?
This year, I’m planning ahead before anyone even asks me what I want. The handbags on my radar aren’t just fleeting trends—they’re the kind of chic, investment-worthy pieces that would make anyone’s holiday extra special. From rich suede shoulder bags to polished leather totes, each one strikes that perfect balance between classic and current. Whether you’re shopping for someone else or (let’s be honest) hoping to manifest a delivery to your own doorstep, consider this your curated edit of the season’s most giftable designer bags.
A Unique Chanel Double Flap
As I expand my bag collection, I’m most interested in investing in the classics, but with a twist. Now that I feel like I have a good foundation for my wardrobe, and a black Chanel Double Flap that I love, my mind is set on finding more double flaps that are unique and have character. Pops of color, cool textures, rare finds—these are all on my radar and I can’t wait to see if I find anything good on my next vintage shopping trip.
Balenciaga Rodeo Bag
Consider this the city bag’s sophisticated older sister. The city bag girl is downtown, spinning behind the DJ booth at every major party. But come Sunday, she’s visiting her big sister’s elegant apartment uptown—the one who’s traded late nights for elevated essentials. This bag is her.
Bottega Veneta Ciao Ciao
The Rodeo bag isn’t the only slouchy and roomy style that I have my eye on. Bottega Veneta’s Ciao Ciao bag might just be my new obsession. It shot to the top of my wishlist when it first launched and I’ve been thinking about it ever since. It is such a minimal style but instantly recognizable by people in the know.
Chloé Paddington Bag
This bag was once loved by the it-girls of the aughts and it’s having a quick comeback. The bag’s oversized hardware and slightly rugged feel make it stand out in a sea of polished, structured styles. It’s nostalgic but in a way that feels surprisingly fresh again. I love the idea of styling it with tailored pieces to balance out its Y2K energy.
Toteme T-Lock Clutch
My evening bag collection is slim. In my early 20s, I was after glitter, sparkles, and colorful details but right now I’m looking for something a little more understated. Thus leading me to the T-Lock Clutch by Toteme. A clutch screams eveningwear yet this one whispers it much more quietly than some of my previous choices. I have so many outfit ideas with it, I don’t even know where to begin.
The Row ‘90s Bag
This one is pure investment piece territory. It’s simple, sleek, and timeless in a way that only The Row can pull off. I love the idea of having a minimal bag like this in my rotation for years to come—the kind that just gets better with age and goes with absolutely everything. It’s the ultimate quiet luxury classic and everyone I know who has bought it, *ahem* Laura Harrier for instance, has no regrets.
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Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of industry experience to the editorial team. Since joining in 2021, she has made her mark by blending luxury and accessible fashion, decoding runway trends, and curating must-have shopping lists. Before joining Who What Wear, Sierra sharpened her skills at Harper's Bazaar and Elle, with bylines in Bazaar.com and collaborated with iconic brands such as Gucci and Ferragamo. A graduate of the University of Notre Dame, Sierra translates editorial expertise into viral social content, making fashion engaging for a new generation. Her unique perspective is rooted in her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.
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