Everlane ‘The Boss Bag’ Review + A Holiday Giveaway!

*Product was gifted but all opinions are my own! 

Everlane Boss Bag with Everlane Croc Loafers

It’s no secret that I’m a fan of Everlane clothes! But I’m also a fan of their leather bags and shoes! So when I heard they were releasing a “hobo” bag I really wanted to try it out. I have a black, slouchy hobo bag from another brand that I wear constantly and I wanted to see how the Everlane version would compare!

Everlane Boss Bag Review

Fashion Blogger wearing the Everlane Boss Bag with Sweater Dress

Style and Construction

It’s called the “The Boss Bag” because it’s meant to be able to go from work to drinks after! It does have a more relaxed, slouchy construction but it’s elevated and sleek at the same time. So it’s totally a bag that’s work appropriate but casual enough to wear out everyday as well. If you are looking for an alternative to a tote bag for work then this is a good option.

It has a TON of room inside. It’s even able to fit my 13″ laptop. There is only one open pocket on the inside of the bag, so there isn’t a lot of compartments to separate items. There are no exterior pockets. Hobo bags are kind of like black holes – you can fit a lot inside but sometimes it’s hard to find exactly what you are looking for!

The exterior is a nice Italian pebbled leather so it feels very sturdy – even though it’s flexible and soft. The pebbled leather means it will be easier to keep clean (especially if you go with the black or burgundy color). The inside is a soft suede leather so if something spills inside it would be hard to clean up. My other hobo bag has a nylon interior which is much easier to clean.

Everlane Leather Boss Bag Review with Laptop


The Boss Bag is a lot bigger than I thought it would be. Which is perfect if you need to fit a lot inside! But I have a petite frame (when I’m not pregnant!) so sometimes bags like this can overwhelm me. BUT unlike a structured tote bag, this bag is made out of a flexible, slouchy leather so it doesn’t take up as much room.

My one complaint is that I feel like the shoulder strap is a bit short. I wish it was a little longer so the bag would lay better on my side and feel more secure on my shoulder.

Since this bag is made out of genuine, sturdy leather it is a bit heavy. So if you fill it up to capacity there is a lot of weight on your shoulder.

Everlane Boss Bag Review

Overall, this is a great bag if you are looking for a sleek work bag. It’s also great for travel because you can kind of fold it up and it doesn’t take up a lot of room when it’s empty. There’s a lot of room on the inside so you can fit a laptop, shoes, wallets, keys, and more!

The downsides for me are the interior design. There isn’t a good pocket to keep items separated. And I feel like it will be hard to keep clean. I also wish the shoulder strap was a little longer to make it more comfortable.

It does feel very high quality and the leather is great! It’s definitely worth the price if you are looking for a sleek, versatile bag with a lot of room!

Outfit Details:
H&M Knit Dress
Everlane Boss Bag c/o
Everlane The 90’s Loafers in Croc

Nordstrom Giftcard Holiday Giveaway

On another note, I’m SO excited for the holidays that I wanted to start the gift giving early!

$500 Nordstrom Giveaway

Time to treat yourself to some Fall shopping at Nordstrom!
I’ve teamed up with a group of bloggers to give one lucky winner
a chance to win a $500 Nordstrom Gift Card!

To enter: complete the steps in the rafflecopter below. The more steps you complete,
the more entries you receive, and the better your chance at winning!
This giveaway runs until Tuesday, November 19th at 12am PST

Winner will be announced here. Good Luck!
*this giveaway is in no way sponsored by Nordstrom.

a Rafflecopter giveaway

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  1. It’s a beautiful bag Jessica! My first bag was a hobo bag so this style will always have a special place in my heart. I love the color and the leather looks supple and soft. I also like how it is a bit more slouchy than some of the hobo bags I have seen or tried on. It helps with my smaller frame!

    Maureen | http://www.littlemisscasual.com