Whether you’re taking a weekend getaway or packing up for a shorter business trip, a stylish, functional weekender bag is the perfect travel companion. We’ve discussed some of our favorite weekender-style bags before, but these bags are so useful and versatile that we decided it was time for an update. All of these bags meet carry-on requirements and are ideal for 1-3 days of travel. Here are our picks for the best weekender bags of 2019.
Check out all our picks below plus a few extra bags that we added for good measure!
A truly excellent bag, we love the mix of waterproof nylon and full grain leather, as well as the simple, lined interior and clean design. An added bonus, this bag comes in multiple sharp color options and also comes with a matching, full-grain leather strap. It may seem like a small detail but the two exterior pockets on each end are a really handy design detail that gives you some extra storage flexibility. The navy and tan colorway we tested was great, but we also really like the olive and black combo.
We’re big fans of Hershel’s backpacks, briefcases, and wallets, so it makes sense that their weekender bag would be excellent as well. This bag boasts a very nice price point that belies it’s sturdy, high-quality construction and materials. It’s constructed with heavy-duty nylon and has an integrated shoe compartment that we thought was a nice feature. While we preferred the basic, monochromatic black and grey colors, the huge range of colors and patterns is a nice bonus if you prefer more colorful options.
As with all things Everlane, this bag has a great price point and super simple, classy design. In our previous weekender video, we chose this one as well, but it had a rubber bottom. In this newer version, they’ve done away with that and added metal feet instead, which we feel is a downgrade. But overall, it’s still a great bag at a great price.
We loved the price point and mix of leather and canvas with the shoe handy shoe compartments and this bag is a really excellent value. The bag has a unique garment bag design to it but in the end, we weren’t a fan of this aspect because it could potentially affect the clothes you normally put in a garment bag as they can get smashed on the sides and bottom. But, other than this small part, this bag was really great.
The Frost River bag is made in the USA and boasts a great mix of affordability and quality. It’s constructed with heavy-duty materials that will age beautifully and last a long time. The leather accents are very nice and the hardware is sturdy. The top zipper design opens up very wide to make packing easier and the exterior pockets are perfect for stashing books, magazines or an iPad, both nice design touches.
Another made in the USA, heritage brand, Filson builds extremely durable, handsome bags that will literally last you a lifetime. If you favor the more rugged, woodsy look, this is the bag for you. It’s constructed of very sturdy canvas, outstanding leather accents, and strong hardware. It has a very large capacity and features a beautiful all-leather shoulder strap. This bag takes some time to break in but will only get better over time.
This stylish weekender bag boasts a sleek, monochromatic design that we really loved. There’s minimal branding and it features very nice cotton canvas accented with Italian leather details. We loved that the entire base was leather, a very nice touch. While the shoulder strap wasn’t all leather, overall this bag is very nice and has exceptional design.
Another outstanding American-made bag, Billykirk is known for their leather goods and excellent quality. This handsome bag is made from heavy waxed canvas and very nice leather accents (including an all-leather shoulder strap!) that will age beautifully. The style is clean and simple but with a bit of a rugged vibe that’s not too over-the-top. It’s really a great mix of modern classic styles. It comes in two great colorways but we especially love the all-black version, it’s really sharp. This bag also comes in smaller and larger versions, so if you’re looking for more or less space but love the looks you’ve got some options here.
Dorian has owned this bag personally for 4 years now and it looks brand new. This bag has it all: clean, classic design, buttery soft tumbled leather that just gets softer with age, an all-leather shoulder strap, lined interior and no metal feet on the bottom. Plus the design features just the right amount of structure to it. It’s a pleasure to own and use this bag, it’s the best of the best.
A stylish and functional bag is one of the most important accessories a man can own and we thought it was high time we updated our previous picks. We love a good backpack of course, but no matter what type of field you work in, carrying your goods in something sharp and professional is important. You’re better than that old, falling-apart school bag.
In this video, we’re running down a batch of the latest and greatest new men’s briefcases and messenger bags for 2019!
We loved the clean, simple design for those looking for a budget-friendly option. It features a clean, no-frills design and is made from rugged canvas with plenty of padding to protect your goods. It also comes with a shoulder strap for extra flexibility.
Another bag with a clean, minimal aesthetic, the Italic bag is a great leather option. It features really nice pebbled leather that feels luxurious, especially for its affordable price point. This bag also comes with a removable shoulder strap (in nylon) and an interior padded laptop compartment. The metal feet on the underside were the real drawback as they can sometimes cause damage if you aren’t careful.
This bag features a nice nylon base with leather accents and matte hardware giving it a very sharp design aesthetic. While not all leather, it would be an excellent option for those of you who don’t work in super formal environments. It has nice details with a ton of functional interior pockets and a nice-looking leather shoulder strap with matching hardware. Overall we really liked this bag and felt it was well worth the price given its excellent design and functionality. It comes in multiple colors too.
Dorian is a big fan of their phone cases so we were excited to see one of their briefcases as well. The Bellroy features really nice leather and a lot of structure, which we really like. It has a clean, functional design and some nice touches with its interior contrasting color and nicely integrated eyelets for the shoulder straps. Two things we weren’t in love with were the leather accented nylon shoulder strap and a little bit of excess branding. It’s on the expensive side but we felt like it was definitely worth the investment for those looking for a modern, structured briefcase.
We’ve featured some of their products before and we’re definitely fans of their high-quality construction and great leather. This bag is on the slim side so it’s definitely for the guy who carries less stuff. It’s got a great minimal design and an exterior pocket for extra storage as well. The interior is very cool and it features a bunch of different organizational compartments for your extra goods and features an interior magnet set up that works with their innovative mod products. It’s definitely on the expensive side but well worth the price for its quality.
These are, to me, the 16 accessories every guy needs to own, regardless of your age, occupation, and lifestyle. Some of these items you may not wear often, but there will be an occasion, as a grown man, when you will need them and you’ll be thankful that you thought far enough ahead to take care of them before it’s too late and you’re scrambling at the last minute. I’ve also included my favorites for each of these items below. But these points below are just skimming the surface compared to the much more through Men’s Essential Accessories Series I did recently.
Like I’ve mentioned before, every man should have at least a grey suit. Even if you only wear it once every year, you’re going to need a suit. Along with that, looking well dressed is always about the details and a white pocket square is an easily overlooked item that really does make a big impact and it’ll only set you back a couple of bucks.
This is another overlooked item. I talked about this in my article about the 12 Things Men Wear That Women Love, but a tie bar is something that adds that special touch to your outfit. It’s also so cheap to own so order it once and you’ll never think about it again.
These two ties will work for any suit you have in your closet, making them an absolute must have. Make sure the width of your tie complements your body type.
Get rid of your white socks. These socks can and should be worn as your everyday socks. If you need heavier duty, thicker socks for your job or because of the weather, there are plenty of companies that offer warmer versions.
Whether you’re a sunglass man or not, sunglasses are important because they’re going to protect your eyes from the sun, prevent you from squinting, which creates wrinkles around your eyes, and they can add a stylish, cool touch to your outfit. Check out my sunglasses story so you choose the right frames for your face shape.
We all have those lazy days, myself included, where you just say F it, I’m gonna throw on a hat. When it comes to baseball hats I have very specific opinions about them so I shared some of my recommendations below.
Not only do these oxford dress shoes look great with your suit, but they also look nice with chinos, jeans, and trousers when you want to dress up a more casual outfit.
Everyone travels. Whether it’s to some exotic country, or across town, you’ll need to put your clothes in something AND trash bags are not an option. Like every accessory you own, it should not only serve it’s purpose, but look damn good at the same time. I have a whole article about weekender bags you should check out.
This item goes great with your weekender bag. Again, doesn’t matter if you’re traveling to another city or to the gym, a dopp kitt is essential because it’ll keep your grooming products organized and contained in a respectable manner.
Depending on what you do for a living, if you live a more casual lifestyle or you’re a student, then a backpack is great. If you are in a more professional environment, a briefcase is best.
Like the last point, which one you go with will depend on your lifestyle. Whether you’re a watch guy or not, any self-respecting man should own a watch or two.
Everyone has casual days, and white sneakers look so sharp on every guy regardless of your age or body type. If you’re really scared of wearing white, or think that it doesn’t look right, ease yourself into it with a nice low top lace-up black or navy sneaker.
The things a man carries tells a lot about him and that’s no more true than with your wallet – check out my article to the left for bifold, card cases, and phone wallet recommendations.
The below are only a few recommendations for bifold wallets.
Okay, so the title is a bit click-baity. I’m sorry, but it’s time we got something straight. There is no scenario when you should be using a messenger bag – unless, of course, you’re a messenger. A messenger bag is the lazy/schlubby version of a briefcase with a removable shoulder strap. Messenger bags look horrible on their best day and any self-respecting man should avoid them. A modern briefcase is much more versatile and works in nearly all casual and dressy situations because of one simple thing: the removable shoulder strap. That little strap instantly turns a briefcase into a classy shoulder/messenger-type bag.
So if you’re hoping to see me talk about messenger bags and won’t consider using a briefcase with a shoulder strap instead, then:
Your briefcase should:
Look classy and timeless as hell – as always
Be free of logos, contrast stitching, flourishes or patterns or needless shine – they’re tacky.
Not be big enough for you to sleep in. – If you need that much stuff, it’s time to sit down and think about your choices in life, or go for a straight up utility item specifically built for this purpose. I’m thinking of those rolling briefcases that lawyers carry.
Carry a 15” laptop easily plus a good amount of items/paperwork, etc.
Have a removable shoulder strap and permanent handles.
Just like your weekender bag and leather backpack, the goal is to have something that shows you’re a man who cares about details and who values the items he chooses to carry with him.
What Material Should A Briefcase Be
In all my testing, the best looking and longest-lasting material is hands down leather. Any other material will stain or wear too easily. I’ve even tested some leather alternative briefcases and they just don’t compare.
What Color Should It Be
You want to stick with black or brown. I’ve looked into blues and gray briefcases and I can assure you that those colors will not age well, both from a style and durability perspective. So please, go conservative with your color choices here. You’ll thank me now and when you realize it’s been 10 years and you’re still carrying the same awesome briefcase.
You may have noticed in my weekender and backpack stories that I said to make sure they’re the same color because they will likely be carried together during trips. This rule can also apply to your briefcase if you’ll be using/carrying it more than a backpack.
When to use the shoulder strap
Just like I said in my backpack story – if you’re wearing a suit, blazer or sport coat, you should never use the shoulder strap. To do so will, at best, wrinkle the shoulder, possibly the lapel, and the back of your jacket. At worst, it’ll ruin the padding in the shoulder. If you’re wearing an unstructured jacket or more casual items, then that’s when to use the shoulder strap.
If you’re not using the shoulder strap, please take it off and keep it in the briefcase or at home.
Just like his weekender bag, this is my hands-down favorite briefcase of the bunch. It’s the same, high-quality leather, awesome hardware and a basic but well-thought out design. LIke all his products, it comes with a lifetime guarantee against any defects.
One of the things I really love about this briefcase is the hidden shoulder strap hooks on the sides. So if you remove the strap, no one would even know that it can be carried over your shoulder. I also love the side pockets on the front and back for slipping things in and out of quickly. It’s just a perfect briefcase in every way.
I have the double gusset version in my video, but the single gusset is also incredibly nice and roomy. I love that there’s options for sizing between single to triple gusset that you usually don’t find with most other brands.
If you pick up this briefcase, please also make sure to get it monogrammed. It just adds that little extra touch of class.
For a more budget-friendly item, I really, really like this one by Coach. They always do a great job with their leather goods, but I have to say, they knocked it out of the park here. The leather feels great, the shoulder strap hooks aren’t hidden like with Frank Clegg’s bag, but they can be tucked into the front and back pockets to be a little more hidden, which is nice.
The interior pocket lining is very soft, almost like a microfiber. The side pockets are also lined with this material. It’s hard to not keep touching it. The shoulder strap could be all leather, but since it’s cheaper than the Frank Clegg briefcase, I’m fine with using some cloth in the strap.
Also, the logo is simply stamped into the leather, and it’s at the bottom of the bag, so major, major points for this. Normally, Coach (and a lot of other brands) would have it placed a little more prominently near the top, but I’m glad they chose the bottom, otherwise this briefcase might not have made the cut.
The one major knock I can give this briefcase is that it has metal feet on the bottom. If you saw my weekender story, then you know that they tend to get scuffed and pitted, which will scratch anything you set these feet on. But just like with the weekender bag, wrap some electrical tape around the feet and it shouldn’t be too much of an issue or be visible.
Over all, I was very impressed though.
Notes about the state of briefcases
So just like with leather backpacks, the pickings are extremely slim in this category, but these are honest-to-goodness the best picks out of the bunch. Everything else was either very cheap or tacky looking or ridiculously expensive for a reason that I couldn’t tell in my testing. Check the Honorable Mentions section below for details about the bags that just missed the cut in case these two don’t meet your requirements.
It looks good for the price, but I thought the quality of the leather was a little iffy. I’d spend a little extra and get the Coach bag, if my budget allowed.
I’m a huge fan of Mulberry, but honestly, they’re about the same price as the Frank Clegg briefcase and I would go for the Frank Clegg 100% of the time.
A weekender bag, or as some people call them – leather duffle bags – are an essential every man should have because like every wardrobe item and accessory you own, it should serve a purpose and look damn good at the same time. A weekender bag’s purpose is to fill the void left when a backpack would be too small and a large piece of luggage would be too big.
If you’re like a majority of my clients (and I, as well), who typically go on shorter trips of up to a week at a time, you’ll be using your weekender more than any other piece of luggage you own.
The requirements for a weekender bag are:
Clean, classic design that is beautiful and functional
High quality construction that’ll last many, many years
Not have too many rivets, embellishments or a tacky logos all over it. 99% of weekender bags fail this test in one way or another by looking too utilitarian or like a billboard for the brand. A gentleman doesn’t need to advertise the brands he owns. It’s low rent.
When to Use a Weekender Bag
You would think this one would be simple, but I see a lot of guys using their weekender bags incorrectly. So let’s go over when you should and shouldn’t be using your weekender bag.
Do use your weekender for:
Going on shorter trips, up to a week at a time.
Any travel when you don’t need your full-sized checked luggage or when a backpack/messengers is too small.
Don’t use your weekender As A
Gym bag
I can’t tell you how many guys I see walking out of the gym with their weekender bags. They’re way too big and nice to be shoving in and out of lockers. If you need a gym bag, get one, or, like I’d suggest, use a backpack instead.
Everyday or work bag
These are not to be used for work. There’s other bags, like a briefcase or messenger bag, that are built for this. And don’t use this bag in place of a tote bag for grocery runs, shopping, etc. it’s definitely not meant for that. You’ll ruin it!
Garment bag
If you need to carry suits or other delicate items, that’s what a garment bag is for. I’ve seen a few weekender bags that have garment bags built into the them and I have to wonder who would put a suit into their duffle bag, and THEN stack a bunch of stuff on top and on the sides of them?
You’re just asking for a horribly wrinkled, or worse yet, ruined suit by doing this. If you need to transport a suit or delicate clothing item, put it in a garment bag and carry it separately or pack it gently into your larger (not overflowing) checked luggage where it’ll have a little bit of space. Weekenders are not the do-all, be-all bags, so please don’t treat them like one.
What Color Should You Get?
Just like anything you carry, you want it to look amazing, so sticking with the clean, classic colors of black, brown or gray is what you want. Any other colors or crazy patterns will not age well and come and go as fashion dictates. If I had to choose, I’d say go with black because browns can tend to show scratches and marks a little more, where black wouldn’t show them as much, that way your bag will look newer for longer. But if you like the aged patina look of a brown bag, that’s perfectly fine as well.
How to match your weekender bag to…
This has been asked a few times, so I want to address how you would match your weekender bag to your other accessories or outfits.
Since we’re sticking to the clean, classic colors, I’d say your weekender should match (doesn’t have to be perfect, just close) your backpack’s color. The reason is because you’ll likely be carrying it along with your weekender bag more than any other bags you’ll own, so a black weekender and brown backpack wouldn’t look so cohesive. If you instead go for a briefcase/messenger bag and don’t have or use a backpack, it should probably match your weekender if you’ll be carrying it along on trips.
As for your outfit, don’t worry too much about matching it to your outfit or other accessories because it’s not part of your outfit like your shoes, belts and watch straps are so it won’t interfere with the cohesiveness of your outfit.
And if you were thinking about asking: Yes, your weekender will look great with casual or dressy outfits, that’s why I consider it an essential.
Quick Tip
When storing your weekender bag, I find that they’re great for storing your scarves, gloves, dress shoes and other items in. Since the bags I’m recommending have some structure to them, they’ll start losing this structure if you’re shoving them under your bed or into a dresser. That way, you can maintain the shape and utilize the empty space.
The Best Weekenders Bags
Please note that all my recommended weekender bags come in multiple colors (including brown), even though I’m only showing them in black or gray, so click through the link to see details and the color options.
This is one of my all-time favorite weekender bags for a few reasons:
The styling is beautiful and classic.
The leather is gorgeous, supple, durable and it has just the right amount of structure to it.
The flap that hides the zipper really distinguishes it against the sea of similar-looking weekenders.
It’s zipper allows it to open extremely wide – this is very rare with most weekenders.
Their customer service is amazing (see the video or below for the story about this)
I had a client who needed a weekender bag super last minute for a press tour. So I called the number on the Frank Clegg website and was expecting a customer service person to pick up, because they’re not a small company, so a man with a super thick Boston accent picks up and says “Yeah, this is Frank”. It honestly took me a few seconds to say something because I was so surprised he actually picked up the phone! I explained the situation and he had a custom bag, including monogram out to me that afternoon for morning delivery. Talk about service!
The last thing that puts Frank’s bag head and shoulders above the rest is that all his items come with a lifetime warranty against any defects. If anything every happens to your bag and needs a repair, call or email Frank and they’ll fix it free of charge. I haven’t seen that with any of the other bags worthy of testing in all the years I’ve been searching.
Out of all the bags I’ve tested over the years, this is the best gray bag I’ve ever seen. The color is just the right shade of gray to not be obtrusive and I also really like the black handles and accents, so it allows you to choose a black or gray backpack to go with it, which are both great choices.
Like all their stuff, it has a little military edge but still remains timeless and classy.I really like that about them – it’s what sets them apart.
If you follow me on SnapChat, you saw Spencer gave me a tour of the production facility and showroom. I’m so impressed by quality of their leather and I honestly think this bag is worth more than they’re charging for it. I also like that it doesn’t have metal feet on the bottom, which can be an issue that I’ll discuss with my next recommendation.
The one unique thing about the bag, which I really liked, is this handle on the side. If you’ve ever struggled with pulling bags out of overhead bins, then you know how valuable this handle is in that situation.
I love that they manage to make high-quality products at an awesome price point.
This is the first weekender bag I saw, before I was a Celebrity Menswear Stylist, where I instantly understood what people meant when they said luxury leather goods. Holy sh*t is this bag gorgeous in person. It also has that iconic weekender/duffle silhouette that’s never been done better. The leather is so soft and supple and dare I say… delicious?
The only knock I have against this bag is the metal feet on the bottom. You have to be a little more careful about what you set this bag on because if the feet become pitted or scratched, it start scratching any surface you put this bag on – wood floors, tables or car roofs and hoods. A simple fix for this is to put a little electric tape around the metal feet every so often so they don’t get scratched up. To me, that’s a small inconvenience, that no one will ever see, for an amazing weekender bag.
At this price point, I haven’t seen a better leather duffle bag. The problem with most bags at a similar price point is that they have really bad designs because they don’t want to use large swaths of leather because that’s more expensive to source and produce. But I think this weekender toes that line very well.
There’s two small things I’d love to see changed on this bag, though.
The zipper should go all the way to the end of the bag, so it’s easier to load and unload the bag’s contents. So when pulling out, say, your dopp kit for the security line, you’re going to have to pack it right in the middle, otherwise you’ll have a hard time pulling it out if it were on either end of the bag.
It has metal feet, which, like I discussed earlier, can be a problem. But a quick fix is to put some black electrical tape on them.
Outside of that though, for the price, I wasn’t able to find something as clean looking or well-made. So kudos to the Combatant Gentleman team for pulling this off.
My second favorite budget-friendly weekender is the Everlane Dipped Weekender. The best feature of this bag, and why it’s the only canvas bag I’ll recommend, is the coated bottom. The problem with other canvas weekender bags is that if you set it down on a dirty or wet surface, this bag would look dirty or be completely soaked, including the items inside, very quickly. With the coated bottom, you avoid this.
Another major bonus is that it doesn’t have any branding on the outside, which plagues a lot of bags at this price point, and the stitching and leather is very high quality. And lastly, if you don’t know about Everlane’s 100% transparent business practices, you should look them up. They’re pretty revolutionary in this respect.
The major downside is that it doesn’t have a shoulder strap, but the two main handles are actually long enough to be used as a shoulder strap, so I wouldn’t consider this a deal-breaker.
Honorable Mentions
These are the weekender bags that just missed the mark for one reason or another.
This one didn’t make the cut solely because it goes in and out of stock pretty regularly. The company has assured me that their stock problems will be fixed soon, but since it’s not readily available, it’s hard to recommend. If you can find it, this would very easily be near the top of my list.
I like this one a lot, but I found it to be slightly expensive for what you got and I had two minor quibbles with the design:
The way they reinforced the bottom could have been done better without using those big hunks of leather on each side.
Even though the leather looks pebbled and matte in the above image, it’s quite a bit more shiny in person. Right on the border of being a little too much for my taste.
This one’s a bit of an outlier because it’s very structured compared to the others, but I liked that about it. The main selling point is that it’s a very well made vegan bag option and has a great price point. So if you’re looking for a leather alternative or want something with more structure, then this one is for you.
That’s it, those are the best weekender bags I could find in many, many years of searching for the perfect ones.
Andrew Snavely from PrimerMagazine.com joined me to compare our lists of the Top 10 Men’s Summer Essentials – with a disgusting twist.
If you don’t know the Bean Boozled Challenge, it’s a game where you have a 50/50 chance of getting a delicious jelly bean or one that’s flavored something like vomit, skunk, rotten eggs and a whole host of really vile flavors.
If our items didn’t match up, we had to spin the wheel of doom and see what flavors we got. I wish I could say this is the first time I’ve played this game, but unfortunately, I’ve had the pleasure of playing it before.
$15 – 
$965 – 
