Oversized handbags are trending again and well, hallelujah, the world is once again feeling New York City! See, we don’t have cars (or trunks or gloves compartments) in which to stash our daily lives, so we just carry our entire lives with with us at all times in oversized handbags all day long. Totes, hobos — real handbags, not like overnighters or duffels because that’s just weird.

Oversized bags are not only practical, but now, evidently, they’re super on-trend and stylish as ever.


(See, when I worked in LA for years, all my colleagues joked that they new I was from New York because I didn’t carry around a delicate tiny handbag for a single lipstick and my phone. Whatever, LA. I’m getting a lot of exercise walking all over town with my big NY handbag.)

Ahem. So anyway.

This time of year, it’s nice to indulge in a brand new handbag to freshen our tired winter wardrobes and get us excited for the “let’s get out more, it’s spring!” time that will be coming up before you know it. Hopefully. That plus a new mascara and you’re golden.

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oversized bags for spring and summer 2024: Go big or go home with this oversized tote from Urban Artisan Boutique

Handcrrafted Oversized Leather Tote |  $191-279 on sale, Urban Artisan Boutique  

If you’re a tote person like me, this is an amazing bag from a Philly-based Etsy artist. She gets great reviews, and the price is incredible: 50-60%% off if you hurry. Also check out her oversized leather hobo bags — beautiful!

Oversized bags for 2024 This yellow leather hobo from an Etsy leather artist is amazing! Helps us look ahead to spring

Oversized Yellow Handbag |  $199 on sale, Linden is Enough

I think this oversized bag is magnificent if you’re looking for a bright pop of color to get you out of the winter dearies. I think I’ll have to do another post about my favorite colorful bags for spring and summer that I’ve been bookmarking. It’s been a long winter. Already.

Related: 24 thoughtful gifts for some of the best women in your lives


Oversized handbags for 2024: Slouchy oversized carryall from Free People is gorgeous in blue!

Oversized handbags for 2024: Slouchy oversized carryall from Free People in tons of colors

Slouchy Oversized Carryall Sling Bag | $78 at Free People*

Free People is always a great size for fairly affordable bags that look a lot more expensive. This oversized handbag is super practical but comes in an array of amazing colors so you can go as neutral or as bold as you want. Love this dusty blue — but check out the yellow!


Oversized handbags for spring and summer: Love Combag's slouchy leather handbags in lots of colors

Oversized Slouchy Leather Shoulder Bag | $176 on sale, Combag

So you say you want an oversized handbag that’s a little more boho? A little more laid-back? A little free-spirited? I have you covered with this  wonderful oversized Italian leather bags that has all the slouch, size and style — plus a little structure when you fold down that top flat. The four S’s. I just made that up. The shop gets super high marks on Etsy.


oversized bags for spring and summer: Longchamps Le Pliage Tote is a classic and not too big at all

Longchamps Large Le Pliage City Tote | $235, Nordstrom 

If you want to ease into the oversized handbag trend with a nice, large, but not unwieldy tote, one word: Longchamps. Listen; these don’t go out of style. I bought my first one in 1999 or so. And only after a ton of use did I finally replace it — with the same style. This will serve you beautifully for years. Also look at the original Large Le Pliage Tote, which costs a little less and is designed to fold up beautifully for travel then unfold and look chic. After all, pliage = French for folding! And French is French for chic. (Kind of.)

Oversized handbags for 2024: Rob & Bone Logan Leather Shopper Bag

Rag & Bone Oversized Leather Hobo Shopper Bag | $495, Nordstrom
(Brown suede version on sale at Rag & Bone)

Okay it’s a splurge designer bag ,but not like $2000 splurge, right? As far as oversized handbags go, oof, I am drooling. The pebbled leather is so refined, it’s beautifully structured and styled, making it a quiet showstopper. Like it doesn’t cream “look at me!” but those who know will look. And ask you where you found it. (Just tell them Cool Mom Picks, of course.)