Ask Painfully Hip: I need a sweet leather bag that’s as roomy as my summer tote

Ask Painfully Hip: I need a sweet leather bag that’s as roomy as my summer tote

Parmida, my friend in Vancouver, sent me this question along with a plethora of links to gorgeous floral and print totes.

So my darling, here is my dilemma: I love totes because they have so much space, but I want a big nice black leather purse to serve the same purposes. I now work and live in a shmucky area of town, so I can’t carry around my totes like I used to. But most oversized purses are quite ugly to me. I like simplicity, classic looks. Can you suggest anything?

When I read this question, I immediately thought of the adorable Irene Adler and her stunning collection of large leather vintage satchels.

I was lucky enough to find a similar bag in burgundy mock-crock designed for laptops for $30 at Winners (aka the Canadian version of TJMaxx), but I’ve also seen a few at thrift stores here and there including one with the tags still on which said Balenciaga, but I’m going to stick to my guns and pretend I was right about my assumption of it’s falsity. I would also do a search on eBay for “vintage satchels.” Try to find one that includes a shoulder strap just in case you’re totally high-maintenance and require the use of both hands, for whatever reason.

But if you’re not as lucky as I am lately (I’ve been bowing down to the gods of karma and begging them to keep that other shoe from dropping), there are some pretty boss new versions to be had online. I’m including leather-like goods as well for the sake of wallet-weakness (and the karma gods).

Lauren’s big brown bag $33 with 15% painfullyhip discount code

Geo retro doctor bag: $61 with 15% painfullyhip discount code YUM.

embossed snakeprint satchel $20


Temperley London bags at

39 comments to Ask Painfully Hip: I need a sweet leather bag that’s as roomy as my summer tote

  • hi again.. thanks so much, i would be sooo honoured to put one of your badges on my site.. but how do i do it? lol sorry if that’s a dumb question but i’m not the most tech-savvy person out there! and by the way, thankyou so much for introducing me to irene adler’s blog.. all i can say is WOW.

  • Great post!!!
    I agree, Ranna has a WONDERFUL collection of bags! She knows I fell in love for the black one (first/last photo of hers).
    I always search for oversized bags! The “Lauren’s big brown bag” and the “Geo retro doctor bag” you featured here are gorgeous, but I saw Lulus doesn’t ship internationally :-(
    I’ll keep going on with the research!

  • i LOVE lauren’s big brown bag. i can’t believe it’s only $33!

  • I never noticed, she does have a lot of satchels! They work beautifully with her look.

  • Parmida

    You are brilliant as always. Thanks, sweet lady!

  • Yikes. It was a bit of a shock to see my pictures of me floating all aroud the place. :)

    I have quite a few of those oversized vintage bags, but that is because I really like to carry my beloved MacBook always with me.
    My advice for those, who seek large leather bags would be that you should never buy one without a shoulder-strap.
    If you do, carrying stuff around will be a real pain in the bottocks.

  • That doctor back with the geometric print is fantastic!

  • Oh… those are really cute! I like these vintage looking leather ones the most. Especially the brown one. I noticed you mentioned some similar looking ones for $30 at a TJMaxx type store. I’ll have to look around locally here and see if I can find one of these. :)

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