Men’s Leather Briefcases & Messenger bags

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:

ariGTFO

Your briefcase should:

  1. Look classy and timeless as hell – as always
  2. Be free of logos, contrast stitching, flourishes or patterns or needless shine – they’re tacky.
  3. 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.
  4. Carry a 15” laptop easily plus a good amount of items/paperwork, etc.
  5. 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.

The Best Leather Briefcases

Frank Clegg Zip Top Leather Briefcase

FrankCleggShoulderStrapHooks

Buy the Frank Clegg Zip Top Leather Briefcase

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.

Coach Metropolitan Slim Brief

CoachMetropolitanBriefcaseShoulderStrap

Buy the Coach Metropolitan Slim Brief

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.

 

Honorable mentions

Shinola Slim Briefcase

ShinolaSlimLeahterBriefcaseAshleyWeston

Buy Shinola’s Slim Briefcase

Love their leather and I like this one a lot, but it’s not as structured as I normally prefer a briefcase to be. So that’s why it wasn’t included.

Uri Minkoff Fulton Brief

uri-minkoff-pebbled-leather-fulton-briefcase-Ashley-Weston1

Buy Uri Minkoff’s Fulton Brief

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.

Mulberry Heathcliffe Briefcase

MulberryHeathcliffeLeatherBriefcaseAshleyWeston

Buy the Mulberry Single Document Holder Briefcase 

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.

Jack Spade Barrow Leather Slim Briefcase

JackSpaceBarrowLeatherBriefcaseAshleyWeston

Buy Jack Spade’s Barrow Leather Slim Briefcase

I wasn’t the biggest fan of the floppy handles and that extra zipper on the bottom is pretty non-sensical.

Weekender Bag

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
  • Meets the airlines’ carry-on luggage size requirements
  • 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.


Frank Clegg Signature Travel Duffel

Frank Clegg Signature Travel Duffel Weekender Bag Holdall Carryall Leather Black Ashley Weston

See details & buy the Frank Clegg Signature Travel Duffel

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.

KILLSPENCER Weekender 3.0

KillSpencer Weekender 3.0 Weekender Bag Holdall Carryall Duffle Leather Black Ashley Weston

See details & buy the KILLSPENCER Weekender 3.0

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.

Mulberry Clipper Leather Holdall Bag

Mulberry Clipper Leather Holdall Bag Ashley Weston Weekender Bag Black

See details & buy the Mulberry Clipper in Black or Brown

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.

Budget Friendly Options

Combatant Gentleman Black Leather Duffel Bag

Combatant Gentleman Black Leather Duffel Bag Holdall Ashley Weston Weekender Bag

See details & buy the Combatant Gentleman Black Leather Duffel 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.

  1. 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.
  2. 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.

Everlane The Dipped Weekender

Everlane The Dipped Weekender Bag Holdall Bag Ashley Weston Canvas Black

See details & buy Everlane’s The Dipped Weekender

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.

Coach Explorer Bag 52

Coach Explorer Bag 52 Weekender Bag Holdall Carryall Leather Black Ashley Weston

See details & buy the Coach Explorer Bag 52

If you want a bag similar to the Mulberry Clipper but cheaper, this is the weekender bag for you.

Shinola Signature Duffle

Shinola Signature Duffle Weekender Bag Holdall Carryall Leather Black Ashley Weston

See details & buy the Shingle Signature Duffle

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.

Uri Minkoff Wythe Weekender

Uri Minkoff Wythe Weekender Weekender Bag Holdall Carryall Leather Black Ashley Weston

See details & buy Uri Minkoff’s Wythe Weekender

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:

  1. The way they reinforced the bottom could have been done better without using those big hunks of leather on each side.
  2. 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.

Matt & Nat – Artigan

Matt Nat Artigan Weekender Bag Holdall Carryall Leather Vegan Black Ashley Weston

See details & buy Matt & Nat 

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.