One of the toughest victories in fashion is wearing a genuinely odd piece without looking like it’s wearing you. Such a feat requires great attention to detail and a sharp sense of styling; if the elements don’t fit together properly, the entire look topples over. It also requires, of course, the taste and willingness necessary to pick the perfect eccentric piece. When all of those things come together, you’ll never see a better outfit.

If you’ve had your fill of the basics and have your bag bases covered when it comes to both neutrals and brights, maybe it’s time to indulge your inner oddball. We’ve got a few bag-centric suggestions, of course, but this is one of those times when you have to listen to your instincts and only your instincts, because your brain will put the kibosh on most of this stuff before your creativity can even kick in to full gear. Check out our picks below or let us know what ill-advised bag you’re currently lusting after in the comments.

Maiyet Peyton Large Lazer Cut Shopper
$2,950 via Net-a-Porter

This bag is perhaps the tamest of our selections, but the stark contrast of the laser pattern and the large scale make it plenty weird in its own right.

Anya Hindmarch Duchess Lady Clutch
$1,595 via ShopBop

Bag with a face on it? Bag with a face on it.

Jimmy Choo Castina Fringe Bag
$5,595 via Net-a-Porter

The lengthy fringe on this little bag recalls a clutch Carrie Bradshaw carried in a particularly memorable late-series episode of Sex and the City.

Nancy Gonzalez Floral Crocodile Small Satchel
$3,500 via Neiman Marcus

Why print flowers on a bag when you can plant them there, in a manner of speaking?

Christian Louboutin Artemis Feather Bag
$2,195 via Net-a-Porter

If you have one (and only one) cold shoulder, this bag might be of service.

Jerome Dreyfuss Carrlos Patchwork Satchel
$1,475 via ShopBop

I’m not sure what to say about this bag because I’m not convinced that I know exactly what’s going on here.

Charlotte Olympia Discover Brazil Printed Shopper
$795 via Net-a-Porter

Charlotte Olympia was nice enough to provide us with a map of Brazil in case we ever get lost.

Sophia Webster Hold Me Speech Bubble Clutch
$450 via Net-a-Porter

Do what the clutch says and nobody gets hurt.

Dolce & Gabbana Miss Dolce Floral Raffia Satchel
$2,995 via Neiman Marcus

The folks at Dolce & Gabbana have adorned their bags with everything from multicolored raffia to fake pasta over the years – they’re old pros at this, and a roundup of bag silliness wouldn’t be complete without them.

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10 years ago

Hahaha. The Charlotte Olympia is actually a funny and pretty summer bag (well, at least in my book). But $800? I don’t think so.

Megs Mahoney Dusil
10 years ago
Reply to  Chris

Yes, these are mostly weird AND expensive!

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10 years ago

I’m totally in love with the Sophia Webster Hold Me Speech Bubble Clutch, it’s quirky and cute and can really make an outfit !

9 years ago

Why should this Maiyet Pez etbe labelled weird? I would wear it with a breezy linen C Z guest look and summery gold flats and bring about the beauty of this laser cut bag.

GG Pastel