Best Weekender Bag 2021 – Buyer’s Guide

Whether you’re heading to Vegas with the squad or staying at your Significant Other’s parents for the first time, you’re going to need a bag that gets your gear where you’re going. The Weekender Bag is your ticket to two days of fun in the sun, craps at the Casino, or long, intense silences with the dad – he knows what you two have been doing and he hates it with all his soul. This little bag of tricks is going to see you through to the other side and get you back to the Monday grind with your cellphone, passport, keys, and clothes still on your debauched person. From duffels to totes these are 2021’s best and brightest weekend warrior’s carry-on bag.

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Best Weekender Bag

 High hopes after seeing the glowing reviews and glossy photos. I was not disappointed! – The workmanship seems top rate, the bag neither flimsy nor heavy as with thick cowhide. It’s got a nice sheen to it but not too shiny like I’m some dandy. Has the perfect balance between rugged casual elegance, and refined, clean lines and style.

Everlane Twill WeekenderTwillCheck Price
Douchebags AffairEVACheck Price
Sweetbriar Classic Duffel Duffle BagFaux LeatherCheck Price
Herschel Supply Co. Novel Duffel BagCanvasCheck Price
BLUBOON Overnight Bag Canvas Genuine LeatherGenuine LeatherCheck Price
BAOSHA Oversized Canvas PU Leather Travel ToteMilitary DesignCheck Price
Toupons 20.8” Large Canvas Travel Tote 
CanvasCheck Price
Aidonger Unisex Canvas Travel BagLeather PouchCheck Price
Haular Overnight Travel Carry OnFaux LeatherCheck Price
Berchirly 21″ Large Canvas Leather Travel BagCanvasCheck Price

Everlane Twill Weekender

This simple and sleek designed bag from Everlane is going to get you where you want to go and look good doing it. This classic duffel comes in a wide range of colors: from jet black to navy to asphalt to mustard, and is going to be your go to bag for your gym clothes, overnight stay, or even a beach day. Made of water resistant twill it is going to be able to stand up to bad weather or unexpected boat trips, while it’s leather handles are sturdy enough to handle any load. The design of the bag, while not necessarily revolutionary, has a spare few surprises for the Obsessive Compulsive in you.

The main compartment is spacious and safe, with a supportive floor backed up by exterior gunmetal feet rivets. There’s an interior document or toiletry pouch to keep all those little essentials separate from your clothing and shoes. An exterior pocket allows you to gain quick access to the wallet or smart phone you really don’t need in your pockets while going through airport security – how many times have I left some last minute addition behind in one of those ridiculous TSA bins? Far too many.

It also comes with a shoulder drop so you never have to use those beautiful leather handles if you don’t wish to. This is also going to save you a hand when you need it most. The issues I have with this bag are not in its construction or the materials used – far from it in fact, everything on this bag is expertly manufactured with high quality materials – but more macro objections. This is a simple bag with a simple design. Its single compartment, like all single compartment duffels, is going to force everything into the same space. Be it your shoes, you dirty laundry, some minibar size bottles of Jack, all of these are going in with your clean clothes. There is also the issue of a lack of side support that may or may not leave your belongings slumping into the middle of the bag and getting wrinkled or crushed when you put this thing in a tight space: like an overhead compartment


  • Classic design with numerous color options
  • Made well and with good materials
  • Leather handles are made with actual leather


  • A single compartment without a lot of organizational options
  • An expensive price tag for what is at its core a duffel bag, can only be purchased from Everlane
  • Lack of side support is going to leave your belongings smashed if placed in a packed overhead compartment

Douchebags Affair

This cheeky bag rides that delicious line between subtle and sexy. Dubbed the Affair by its creator Douche Bags, you’re going to understand the intention right away. But this isn’t the bag you take to some seedy motel on the edge of town to meet up with your strangely alluring dry cleaner in order to engage in a ten minute bout of “Who’s got the most frustration bottled up inside”. Rather, this is the bag you’re going to want to pack before heading off to do some “business” in Soho or Las Vegas – I like to call it Lost Wages – where you may or may not lock eyes with an elegant enigma searching for something more out of their night. With plenty of room for evening wear, lingerie, toys and maybe even some leather accouterments, this jet black polyester bag is the key to preparing for your illicit weekend rendezvous.

Douchebags has truly pulled out all the stops with this little number. With an EVA protective shell all of your delicate or finicky bits and bobs are going to arrive safe and sound at their destination, while the bag’s adjustable straps allow you to expand its carrying capacity. This is an essential quality in a compact bag and one that should not be over looked. But the reverse side to that coin is just as important, tightening your bag’s straps so that its contents are stored compactly is going to save you room and keep the contents within from jostling around, wrinkling or breaking. No one wants or needs a lot of loose material and useless space in a bag, it’s unsightly and a risky move. When adjusting the two buckles at the top of this duffel you can double it’s size or shrink it to a compact, protective carrying case.

And don’t worry, you’re not going to have the word “Douchebags” emblazoned across the front of your bag in hot red, capitol lettering. The designers, sensible to the possibility of offending the masses, have settled on just the letters “Db” to let people know who the maker is. Some people will know immediately who made that bag for you and you’ll share a small wink over a private joke. Who knows? That just might be how your naughty little getaway really get’s going.


  • Adjustable straps let you hold more or batten down the hatches on less
  • Padded EVA protective shell is going to keep your belongings safe inside
  • A stowaway adjustable shoulder strap


  • Comes in only one color: jet black
  • The most expensive bag on the list, this can only be purchased from Douchebags online store
  • There may be a slight social stigma to toting around a Douchebag

Sweetbriar Classic Duffel Duffle Bag

This particular Vintage style top-handled travel duffel weighs in at a very reasonable $39.95. Clearly inspired by the Herschel Novel Duffel, Sweetbriar has developed a near clone at a better price. Complete with a side access shoe compartment, removable shoulder strap and over the top faux leather handles, this sexy thing is both sensible and stylish.

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Best Sweetbriar Classic Duffel Duffle Bag

Worth the price! – love this bag. It’s a simple, straight-forward construction. A spacious interior with an small zippered pocket inside. On the outside there’s a pocket at the bottom that’s made for shoes. It works for weekend overnight trips. It is a pretty decent size.

What you’re getting here is an easy living bag, not something to pack tight and bring to the great outdoors. It looks a lot more expensive than it is – a plus – but be wary of its capabilities. But let’s talk about the good bits. It’s a beautiful bag that is big on style points. The shoe compartment is large, large enough for two pairs of flts if you’re smart about it. In fact, this whole bag is roomy as hell. You easily have enough space for three to four days worth of clothes with room left over for your swimsuit. The interior lining is a nice touch, keeping your clothing away from the outer canvas that, due to mishandling, could end up wet or muddy.

You’re going to get a varying amount of mileage form this bag as it suffers from a few obvious problems. It has a single interior pocket for your toiletries or electronics but the lack of any additional pockets forces you to put the rest of your personal items in the same compartment as your clothes. That means your keys, your passport, your travel documents or phone charger are rattling around with your underwear and socks – sure to get lost at the exact moment you need them. The faux leather straps are not entirely reliable and the canvas itself is not heavy duty. It’s zippers are also not up to snuff: small gauge and delicate, you are going to have some problems due to breakage or (because of their lack of water-proofing) water getting in. Beware of rainy destinations and yanking. Seriously, don’t yank.


  • Includes a removable and adjustable padded shoulder strap for those long walks through the terminal or train station
  • A separate side access shoe compartment to keep those dirty sneakers away from your threads.
  • Stylish and reasonably priced at $39.95


  • The small gauge zipper is delicate and out of place on this sturdy canvas carryall.
  • The leather straps are prone to ripping under heavy use
  • Made of low-quality nylon that will wear and stain easily
  • Comes in only one color: gray

Herschel Supply Co. Novel Duffel Bag

Backed by their Limited Lifetime Warranty, Herschel is known throughout the world for their quality products. This particularly beautiful bag comes with a ton of optional colors and designs – from pastel petals to woodland camo it’s hard to find a scheme that doesn’t look dead sexy. With its signature shoe compartment and removable shoulder strap this duffel is expressly designed for the efficient traveller.

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Best Herschel Supply Co. Novel Duffel Bag

Good for a weekend. Love the shoe compartment. – Absolutely love the Herschel company but always thought they were so expensive, well ended up needing a decent sized bag for a trip over the summer and this was the perfect choice. Very impressed with the sturdiness of the handles and zippers, it is definitely not like a cheap one you can just grab from a basic store.

This particular duffel is the standard by which all other duffels are judged. From its top-quality canvas body to its signature striped lining (always classy), it’s guaranteed to look good on you. Other great features include a comfy pad on that shoulder strap, great internal structure so your belongings stay where you put them and don’t sag to the middle, plus both an internal and external pocket to keep of your toiletries, electronics, and travel docs separate from your clothing.

But Herschel may have gone with style over substance with this duffel. Just because it is backed by that famous warranty doesn’t mean you should ever have to use it, but with delicate plastic strap clips, weak stitching around the handles and small gauge, delicate zippers, you very well may have to give them a call sometime in the future. I mean you’re paying upwards of eighty dollars for this bad boy, it should be fire and forget. The biggest red flag is the use of plastic. Plastic has no place on any respectable, heavy-duty duffel. Herschel baby, spring for steal.


  • Elegant and stylish bag coming in a variety of colors and schemes
  • A removable shoulder strap will let you keep both hands free
  • Perfect carry-on size
  • A Limited Lifetime Warranty, so in the event of a breakdown Herschel will reimburse you


  • Delicate straps and zippers are prone to breaking after moderate use
  • Plastic strap clips are easily broken
  • Fake leather doesn’t stand up to long-term use
  • Overpriced at $84.99, you’re paying a lot for that Herschel badge

BLUBOON Overnight Bag Canvas Genuine Leather

This particular peach is both functional and fancy. From its vintage leather dressing to it’s sturdy, canvas body, this overnight bag is going to please the eye and keep you spry. Coming in army green, coffee and grey, you’ve got a few dusky options to choose from. There are also nine interior and exterior pockets. Nine! No more fishing around for those essentials, you’ve got yourself almost too many options for organization.

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Best BLUBOON Overnight Bag Canvas Genuine Leather

Great well made bag! – The bag was very comfortable to travel with also. The strap works well ,bag is really a good size to carry, This bag is perfect for me! Colour is nice, leather accents are a nice touch, the zippers run smooth with no catching, the interior lining is good and there are pockets enough for everything one is zippered. The two end pockets on the outside are a good size.

This Bluboon bag is sturdy and ready to go. The zippers are large and waterproofed with thick leather pulls so they’re rarely going to be stuck. The straps are reinforced with stitched leather holds and the removable shoulder strap is attached with metal clasps. Everything about this bag screams reliability. You don’t have to worry that the handles are going to rip off if you happen to pack your bowling ball, nor are you going to have to pull out those pliers to get that zipper from point A to point B.

Ends up though that this bag is actually quite small. Despite the photo on Amazon of a man carrying it on his shoulder where it looks large enough to bring nearly a weeks worth of clothes, this little guy is going to have trouble enough with just two days of gear. There’s also the little problem of its lack of support. You’re looking at a bag that is going to sag on the sides and the bottom unless you have packed that thing to the brim. This is definitely going to cause some wrinkling and thus some annoyance.


  • High-quality canvas body with genuine leather decoration
  • Nine pockets inside and outside the bag for easy access to travel documents and identification or safekeeping for small toiletries and electronics
  • Waterproof, heavy-gauge zippers


  • No support means this bag will sag unless completely full and the bag’s contents will shift to the center.
  • Smaller than you would expect, might not serve your needs for the full weekend
  • Maybe a bit overpriced for a canvas bag with some leather trim

BAOSHA Oversized Canvas PU Leather Travel Tote

This Baosha bag is a cheaper clone of a Berchirly bag we’ll see later in this list but that doesn’t mean it lacks in quality or character. A classic military design with an impressive amount of packing space this duffel is a real steal for just under $40. Coming in black, blue, army green and grey, you’re going to look good carrying this guy around. It just oozes experienced traveller.

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Best BAOSHA Oversized Canvas PU Leather Travel Tote

Good quality bag, looks expensive. – This a great sized weekend bag – a lot of weekend bags tend to be smaller and better for an overnight trip – if you are looking for something that will be good to pack all your stuff for a 2 night weekend trip and want to avoid a traditional duffel bag or larger suitcase – this is a great bag to consider.

It’s built to last, made of heavy-duty canvas reinforced with bi-cast leather lining and handles even the zippers on this bad boy are heavy gauge with leather pulls. But the size of this bag is the real star of the show. You’re going to be able to last not just the weekend but almost a whole week if you pack this thing right. In that case the canvas shoulder strap is going to be pretty essential to your comfort, even though it lacks a strap pad, which very well may lead to some discomfort over a long carry.

There are some slight structural problems with this bag as well, it tends to collapse on you due to its construction and it can sag if not packed right. This is, again, a small nightmare for the obsessive packer. You’re going to open this thing up on the fly and realize everything is jumbled into the bag’s center rather than where you carefully placed it. A little structure goes a long way towards piece of mind, something that you really can’t put a price on.


  • An excellent deal at $39.99
  • Bi-cast leather handles and zipper linings that hold up like the real thing
  • Sturdy canvas shoulder strap
  • A Lifetime Warranty: 100% cashback for your damaged bag. That’s pretty legit.


  • Bi-cast leather can be a bit shiny and look fake, not many people are going to notice but it’s really about you knowing and caring
  • Structural problems that cause sagging when not packed to the rafters. This is going to lead to wrinkled clothes

Toupons 20.8” Large Canvas Travel Tote

This many-pocketed tote bag is perfect for keeping all your travel essentials organized and ready to use. The canvas looks great and holds up to wear and tear while the handles, similarly canvas, are made to last. Coming in black, blue, coffee, grey and khaki, you’re going to find the color for you.

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Best Toupons 20.8” Large Canvas Travel Tote

Looks great. Good size when it’s extended – Even the sturdiest duffel bag can only aspire to be sturdy. It looks upon other types of bags with wonder, hope and sometimes jealousy at their superior sturdiness, Looks great. Good size when it’s extended.
Same height and length as most roller boards. Smaller width that roller board.

A real perk of this bag is that is expandable. Simply by unzipping the sides you’ve just gained yourself a few valuable inches of room. Got yourself a surprise gift from a thankful mother-in-law come Christmas time? Guess what? You’ve now got room to take it home. Depending on what it is…hooray! Besides that hopefully glorious trinket, you’re going to be able to fit a whole lot in this bag. Did I tell you about all the pockets? I might have mentioned something about it. You’ve got three exterior pockets for all those useless Yuletide knick-knacks and doo-daws you just got saddled with.

With all that said the expandable qualities and pockets don’t mitigate the fact that this bag isn’t very large. You might struggle to get more than a couple day’s clothes inside. There have also been issues with faulty stitching and tearing. When you buy a bag for this low of a price there should be some expectation of a comparable level of quality but this really isn’t a constant or common problem with these bags.


  • Many pockets to keep all your documents, toiletries, and electronics organized and ready to use
  • Expandable, so you’re getting a bit more room than you thought you would.
  • Heavy-duty zippers with canvas pull make packing this thing tight less of a hassle
  • Very affordable


  • A smaller bag that might not get you as far as you want to go
  • Stitching is unreliable in some cases

Aidonger Unisex Canvas Travel Bag

This is Aidonger’s version of the Toupons Tote and boy howdy does it hit in the same weight class. It’s got the pockets and the expandable sides. It’s got the adjustable shoulder strap with sliding pad. It’s even got the cotton lining and comes in the same colors. So what’s the difference between the two? Well this one is a few dollars more expensive and – drum roll please – comes in two separate designs.

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Best Aidonger Unisex Canvas Travel Bag

Stylish and Serviceable Good Quality Duffel Travel Bag with Leather Accents – This Aidonger Canvas and Leather Travel Bag more than met my expectations both in quality, serviceability, and style. The overall main duffel is made of heavy canvas. The accents and the handles are made of supple brown leather. he handles are thick and the leather is smooth. They are held together by a leather handle wrap that secures the two handles together with a snap button.

The alternate design ditches the front zip pocket in favor of a stylishly rustic leather-covered pouch. I actually love this design because it adds a lot of character to what could be seen as a fairly common bag. It’s incredible to me how just this little leather addition changes this bag from “Ok” to “Oh my God!” It gives it a vintage, retro, adventurer vibe that is going to make your fellow travellers look twice and get a little jealous. With this small shift in design you’re getting a lot of fashion bang for those three extra bucks.

The problems with this bag are similar to that of the Toupons bag. It is a smaller bag than you are expecting it to be so you will not be packing this thing up for more than two or three days of travel. Even with it’s expandable sides this tote isn’t going to get you very far, but it’s still a nice feature. Depending on the bag you get you may have some problems with the stitching and zippers. It’s sort of luck of the draw in these scenarios.


  • A 1-Year Warranty with a 100% satisfaction guarantee really goes a long way to giving you peace of mind. Until that year is over. Then you’re screwed.
  • Straps are reinforced with rivets
  • Alternate design kicks ass


  • Unreliable strap stitching
  • Suffers a similar size problem to the Coupons bag above, exclusively a two-day weekend bag
  • Zippers can come off their tracks
  • Not waterproof so keep it out of the rain

Haular Overnight Travel Carry On

This classy faux leather number is exactly what you’re looking for in an overnight bag. It hits all the marks for style, sophistication and overall design. What looks like a single compartment bag actually contains seven separate pockets and compartments for easy organization and easy access to your important belongings. The lining is a playful green striped motif that contrasts very nicely against the severe black leather exterior. The “Haular” name is emblazoned across the front of the bag in subtle and distinguished brass lettering.

This is the style of bag you could see slung over the shoulder of an up and coming business person or clutched in the manicured paws of the rich and famous. Its expandable straps allow you to carry way more than you would have ever expected while the bag’s surprisingly light-weight let’s you take on those heavy items.

But this isn’t an ad for Haular’s bag. This thing’s got a real problem and sadly, once again, its with the zipper: it sticks, it snaps, its stitching comes apart. This is an unforgiveable sin to any jet setter. If your zipper is unreliable then your bag is unreliable and all you belongings are at risk. It helps that in most cases the company will offer to reimburse you for the damage but it really is the principle of the thing that gets me. There is nothing more annoying than having to return an online purchase a few days after you’ve received it. Nothing quite so aggravating as having to compose a strongly worded email to a company that you know will appease you right away but will never feel your pain. This bag is relatively expensive so you expect better.


  • Faux leather body and handles with brass accents and rivets give this a classy and sophisticated look
  • A large compartment that holds quite a lot
  • Comes with a removable and adjustable shoulder strap
  • Water-resistant
  • Seven interior compartments and pockets give you a lot of organizational options


  • Not real leather. Some people will notice, most won’t. Depends on your crowd.
  • Zipper issues up the wazoo. If you have this problem contact the company and they will help you out

Berchirly 21″ Large Canvas Leather Travel Bag

You’ve seen this bag before and you’re lucky to be looking at it now. It’s a classic. A beauty. Not to mention a good deal. But I’ll admit I’m biased. This in coffee – it comes in grey, khaki and army green as well – is, by a long shot, my favorite bag of this entire list. From the leather details to the metal rivets something about it just screams at me to get up and go someplace new. Somewhere that I’ve never been before where desert sands shift under hot winds or pitted stone walls open up onto cobblestoned alleyways. There’s potential here to wander and search. A potential that is hard to put into words.

The bag itself is made of a sturdy canvas that is not going to breakdown on you. The lining inside is charmingly utilitarian and sports two internal pockets and two zip up compartments. The front of the bag also has two zip-up pockets for your passport and such. The main compartment is very large and should be big enough to support belongings for trips of up to three or four days.

The problems with this bag are few and far between. The shoulder strap it comes with is made of light brown canvas that may or may not match the rest of the bag. This can look a touch ridiculous and may be a death sentence for the fashion conscious among you. The bag, admittedly, has a military look to it that may seem out of place on a business trip or luxury vacation getaway.


  • Genuine leather straps and details
  • A beautifully made bag at a beautiful price
  • Sturdy canvas body that won’t break down
  • Metal rivets to provide support to straps


  • The canvas shoulder strap comes in one color: light brown. So be wary that it might not match your choice of bag
  • Lack of support may cause wrinkling or crushing when placed in packed overhead compartments

And there you have them, from Douchebags to Travel totes, from faux leather to the true cow’s hide, these are 2021’s murderer’s row of Weekender bags. Now it’s all up to you. Pick your poison, pack it up and get ready to spend those Saturdays and Sundays jet-setting around the globe or just staring pleadingly into your Significant Other’s eyes as their parents ask pointed questions about all those much more successful and better-looking exes they used to date. Have fun!

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