Love It or Leave It: the Return of the Hobo

The hobo is back—big time, but are you ready for its triumphant return?

Do you ever wonder what happens to trends of the past? Do they sit in limbo just waiting for someone to remember they exist, or do they go to some sort of fashion heaven to rest in peace for good? Some trends, I’m sure, are meant to die (Dad sneakers I’m talking to you), but others were really solid, well-liked and found their way into our hearts. Do you remember when hobo bags were all the rage? I’m sure your favorite reformed boho celeb does. Just ask Jessica Simpson during her Newlyweds days, or Lauren Conrad on The Hills. Hobos were a thing for quite a while, and looking back it’s pretty clear why. Hobos were easy, grab and go, kind of bags. Not to mention, they were relatively practical as well. Many were roomy enough to, well, hold your whole life in the crook of your arm. Slowly the hobo trend kind of lost steam, though I wouldn’t say that it completely died. Every season a few would pop up here and there amongst designer line-ups, but the trend never came back full force. However, this season might be the season it happens. I’ve been saying it a bit under the radar for the last couple of months, just ask Megs, and then I saw that Vogue was thinking the same thing and I knew I was on to something.

I was never a hobo girl at the height of the trend. I preferred totes, or top handle bags back then, and now, you all know I love a good mini bag. While I can appreciate that there are a lot of nice hobos popping up here and there now that this trend is on its way back, I’m not sure that the hobo is for me. It’s not that I don’t like it, but rather I don’t know that the hobo exactly fits my style. What about you? Do you love it or would you rather leave it? If you’re here for it I’ve got ten styles to get you started on the return of the hobo.

Gucci GG Supreme Large Hobo ($1,490)

Burberry Grommet Medium Leather Hobo ($1,990)

Wandler Corso Hobo ($810)

Bottega Veneta Maxi Veneta Intrecciato Hobo ($3,000)

Loewe Small Hammock Bicolor Hobo ($2,490)

Jimmy Choo Stevie Hobo ($1,350)

Prada Oversized Hobo Bag ($1,990)

MiuMiu Grace Hobo ($1,790)

Altuzzra Ghianda Large Knot Hobo Bag ($2,295)

The Row Suede Hobo Bag ($1,190)

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JHH

The Hobo can’t be back. It never left.

Divadeluxnyc

Hobo is never OUT of style IMO

Laura

Hi! I love hobos, too. I’m thinking of designing one for my new line of bags and would love to ask your opinion about a few things. For instance, what features do you like or not like in a hobo? Do you prefer a shoulder, crossbody, or convertible strap? Do you prefer totally smooshy bags or semi-structured ones? Favorite closure? Favorite colors? What would your dream hobo look like?

Thanks in advance for your help!

Jaime Gray

I’m all about a purse being big enough to actually hold things besides lipstick (yes i’m talking about you LV). I really like the color and style of the Burberry.

Sparky

Beautiful but I prefer bags with some structure

Amazona

There are hobos that have structure. Just got me one that’s made of sturdy leather and it has a leather lining so nothing sags. Plus it has a wide base. Things stay organized and the bag looks amazing. It’s like with any other handbag – you just have to find the right one for you.

LW

I’ve always liked them, and will always carry them regardless of whether they’re “in” or “out”.

Laura

Hi! I like hobos, too. I’m thinking of designing one for my new line of bags and would love to ask your opinion on them. For instance, what features do you like or not like in a hobo? Do you prefer a shoulder, crossbody, or convertible strap? Do you prefer totally smooshy bags or semi-structured ones? Favorite closure? Favorite colors? What would your dream hobo look like?

Thanks in advance for your help!

Kweenhelene

Not a fan. Everything falls to the bottom. I had one or two but I would have to put all of my little essentials in make up cases so I could pull them out instead of fishing around and that made the bag even heavier.

FashionableLena

As much as I like the look of hobo bags, I don’t find them functional. It’s like putting your stuff in a trash bag.

Laura

Hi! I’m thinking of designing a hobo for my new line of bags and would love to ask your opinion about them. Would there be any design that would make one functional for you? Like maybe a half moon shape bag with interior pockets? Or is that not the style you like?

Thanks in advance for your help!

Alex575

Half-moon shape, top-zip (for security), slim profile (but that’s not a deal killer for most hobo fans), inner zip and slip pockets, and adjustable shoulder strap or additional ones to wear cross body.

Laura

Great! That was exactly my plan! I hadn’t thought of the interior zip pocket, though. Great idea. Thanks!

Bryan Lepe

Hobo styles are so ugly, unflattering and dated. They are NOT flattering on women’s bodies in any way. I think people forget to look at that aspect when shopping for bags too.
HOWEVER
wear whatever the hell you like and what suits your needs. If a giant sack that juts out 8 inches away from your body and looks like an overfilled colonostomy bag suits your daily needs and lifestyle. Go for it.
Who cares about what others think.
Some people hate that men wear bags and they’re only for women (even though most houses have men designing them haha go figure)
But I’ll keep wearing whatever I want. It’s not paid for by anyone else whose opinion matters.
Some people hate certain bag styles.
If you like it, wear it. Wear the hell out of it. Enjoy it.
If they don’t pay your bills or feed you, pay them NO mind.

Can’t wait to be told I’m snarky and condescending lol.

C

I completely agree! I think hobos are extremely unflattering. I always consider whether a bag is flattering (in addition to whether it is functional and well-constructed).

Donna Warder

You’re snarky and condescending. I loved reading your post! LOL!

Yaffa S. Porat

You are a riot. Yes, express your opinion! I never thought of a bag as “an overfilled colonoscopy bag”. I hate tiny bags. They drive me crazy. BTW, you are snarky and condescending and I love it.

Alex

Hey Purseblog, can we get Bryan to be a writer on this page? We could really use his perspective. He always contributes perfectly stated comments!

Bryan Lepe

I really really appreciate the support. I’d love to bring a different view on bags. A little bit more of the thought invoking side of fashion. Thank you. It means a lot.

Megs Mahoney Dusil

Do you want to?! Can you shoot me an email – [email protected]

I’d be down with it!!

Ms. L

You crack me up.

Gayle

Haha i agree ? i hate this style so much along with the drawstring style. I like bags with pockets not like this everything just falls in the middle

inkfade

I love hobo bags, but with pockets inside too for some organization. Though I like big or medium slouchy bags that can still be worn crossbody, I don’t carry much so they’re never very heavy or weighed down. Many hobo bags to me look carefree and eclectic, whereas very structured or rigid bags look like you’re trying too hard to stay within the lines, in a sense.

Laura

Hi! I love hobos, too. I’m thinking of designing one for my new line of bags and would love to ask your opinion about a few things. For instance, what size & type of pockets do you like on the inside? Favorite closure? Favorite colors? Favorite lining? What would your dream hobo look like?

Thanks in advance for your help!

Amazona

Hobos never went away IMO. Just got myself a hobo for bday present. Sold my M Effie because it just didn’t work (shoulder strap too short, leather too soft) and got a Tiger of Sweden Proclus instead. A hobo is just so convenient – it goes well for both work and free time, it’s comfy to carry, feels safe because it sits under your arm, plus with more structured leather and a wide bottom it’s easy to keep tidy inside so you can find your stuff.

Sibel

For the love of god please add some top zippers to these bags UGH

Electricboots

I have never liked Hobo bags. Not in the earlymid aughts and not now. They just look sloppy to me. To each their own!

Donna Warder

I somewhat agree. But they hold everything. I wish someone could make a structured hobo. Does that even make sense?

Heidi

I loved Hobo’s when I worked. However, since I recently retired I’m more interested in crossbody and camera bags. The functionality of these bags is perfect! They carry what I need, leave me hands free and don’t slip off my shoulder as I’m running after my grandkids. 🙂

Linda Garrido

I love hobos, and am so glad they’re making a come back. Time to dig up my beloved LV Galleria!

memsy

Love hobos. They’re a classic design.

Donna Warder

So hobos have returned. Was there a period during which I was NOT supposed to be carrying a hobo? Oops, missed that one!

Chelsea Girl

I have many many bags, from totes, to crossbodies and mini. However, I got the LV lockme hobo as a present for Valentine’s day. Never thought I’d ever say this about a Hobo but finally, a bag that meets all of my needs all in one, how have I lived this long without one until now?

Jerri R

Nothing else fits the kitchen sink I carry around!

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