Oversized handbags are trending and well, hallelujah, the world has finally caught up with 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.

Overnight 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 little 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.

Now that some of us are getting out more — masked still, of course — it’s nice to indulge in a new handbag to freshen our spring and summer accessories, maybe distract from our overgrown roots, leggings still passing for pants, and skin that’s desperately in need of a facial. That plus a new mascara and you’re golden.

Okay, so this has become a very personal post all of a sudden. I’m okay with that.

Speaking of which, Mother’s Day is coming. Okay! Enjoy these picks!

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

Handcrrafted Oversized Leather Tote |  $224 on sale, Urban Artisan Boutique  

If you’re a tote person like me — room for masks, extra masks for the kids, even more masks for strangers, and of course all your stuff — this is an amazing bag from a Philly-based Etsy artist. She gets great reviews, and the price is incredible: 50% off if you hurry.


oversized bags for spring and summer: This yellow leather hobo from an Etsy leather artist is amazing!

Oversized Yellow Hobo Bag |  $134, Barbara’s Leather Handbag Design

I think this oversized hobo is magnificent if you’re looking for something a little more “handbag” than tote. And the color makes me so happy! In fact,  I think I’ll have to do another post about my favorite colorful bags for summer that I’ve been bookmarking. It’s been a long winter, yo!

Related: Save vs Splurge: Some of my favorite spring fashion trends to fit any budget


Oversized handbags for spring and summer: This puffer sling bag from Free People is magnificent!

Oversized Puffer Sling Bag | $78* at Free People*

*I was super sad to see that by the time I hit publish on this post, this gorgeous oversized sling had sold out. (What is the emoji for “sad impulse shopper face?”) However I did find a new one, no tags, resold through Poshmark for just $55 and another on Mercari for $62. Grab it while you can. This color is amazing and the fabric is so fun.


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

Oversized Slouchy Leather Shoulder Bag | $170, Combag (now 10% off)

So you say you want an oversized handbag that’s a little more boho? A little more laid-back? A little free-spirited, summer is coming, but I’m not going for a full-on woven beach bag kind of thing? I have you covered! Check out this wonderful option from Combat which 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.

(Also check out other colors like the Large Leather Shoulder Bag in brown, which is a nice four-season color and even more boho.)


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

Longchamps Large Le Pliage Bag | $190, Nordstrom 

If you want to ease into the oversized handbag trend with a nice, large, but not unwieldy tote, I have your back. 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, and folds up so well for travel should we ever get to do that again. Plus, there’s a nice navy and taupe which you may prefer for the warmer months.  (I’m always good with black, if you couldn’t tell.)


oversized bags for spring and summer: Dagne Dover large cotton tote in pretty pastels

Dagne Dover Large Cotton Tote | $145, Dagne Dover, some colors available on Nordstrom

Dagne Dover has never steered us wrong — Kristen and I are both big fans. Loving their new organic cotton tote for S/S2, which isn’t huge, but can still fit a 16″ laptop in that interior pocket along with all your other stuff. They’ve got five colors, from the classic neutrals to pretty pastels in yellow and blue. (They actually call this one “pollen” but that doesn’t have the best connotations for those of us allergy sufferers.)


oversized bags for spring and summer: For a splurge, this large hobo from Chloe is amazing
Chloe Large Darryl Leather Hobo | $2,090, Nordstrom

Okay okay it’s a total splurge designer bag but as far as oversized handbags go, oof, I am drooling. That neutral “motty grey” (AKA putty) is so refined, it’s beautifully structured and styled, making it and paint-the-town- (via safe outdoor dining) ready. I love this though it’s not in my budget at all. But hey if it is for you, more power to you! Get it, then tag me on Instagram so I can live vicariously through you and your Hamptons house or 110-foot party yacht.