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:

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.

The Best Leather Briefcases

Frank Clegg Zip Top Leather Briefcase

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

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

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

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

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

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

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

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

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

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.

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.

Everlane The Dipped Weekender

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

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

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

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:

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.

Matt & Nat – Artigan

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.

Leather Wallets

Like I said in the series Intro Video, the things a man carries on his person projects and influences his life and personality in ways he may not notice. And this is no more true than with the little piece of leather or fabric that he carries every single day – his wallet.

I’ve seen it all when it comes to how men carry their cards and cash. I’ve had clients with no wallets who just carry a bunch of loose or rubber-banded cards and cash in their pockets, while others carry these massive monstrosities that I wince at just thinking about how uncomfortable it must be to sit on something like that all day.

As I mentioned in my 10 Most Overlooked Style mistakes ebook, full pockets ruin perfectly good outfits. I see it all the time. The sad part, is a lot of wallet manufacturers continue to sell these massive and bulky things they call wallets. I often wonder what man would see these and think this is something they should carry everyday for the next decade.

I’m going show you the different wallets I recommend to my clients.

There’s a few things that every gentleman’s wallet should be:

Clean & classically designed
As thin or small as possible
Understated in color and material

So let’s get into the different types of wallets that are best for you and determine what to have and why.

Bi-fold or Bill Fold wallets

These are the ones you probably envision when thinking about wallets. These typically go in the back pocket, but some men carry them in their front pockets. I don’t advise this, though, because it’ll leave a very noticeable buldge and, depending on the pants, a very odd square fading on the leg.

Valextra – Simple Grip Spring

Buy the Valextra Simple Grip Spring Wallet

The only word that comes to mind when I hold this wallet is luxury. The textured leather and construction feels, pardon my french, so f@#$ing good. I really love the classic design.

This wallet is the thinnest of all the billfolds I’ve seen, which is important because if a wallet is thick while it’s empty, imagine what happens when you start filling it?

The thinness is made possible by nixing the bill slot and using a spring-loaded money clip in the middle. There’s other wallets similar to this by other designers, but they were either not great quality, had a logo all over them, or just had an odd pattern or design.

If you want something almost as thin as a card wallet, but with the ability to hold cash, this wallet is the best I’ve ever seen. That’s on top of it’s impeccable attention to detail, like the hand lacquered piping along the edges that’ll keep this wallet looking new for a long time. If you can’t tell, I love this wallet.

In the video, I have a special edition Petroleum blue, but I also love their dark blue, black and gray colors, as well.

Buy the Valextra Simple Grip Spring Wallet

Bellroy – Low Down

Buy the Bellroy Low Down Wallet

If the Valextra wallet isn’t your speed then definitely go for the Low Down.

I’ve recommended this wallet to a few friends and clients and they’ve held up amazingly well, even after a year of daily use.

The tapered corners and shorter height help make it feel less chunky and big. And the leather is sturdy yet supple without a hint of shiny or glossy-ness which plagues a lot of wallets.

There’s one thing that bothers me a little and it’s the contrast stitching. I wish it was the same color as the rest of the wallet, but it’s an admittedly small quibble since it’s close enough in color that most people would never notice.

The black and charcoal are the colors you should go for. I normally like brown, as well, but their brown and blue colors were too loud.

Buy the Bellroy Low Down Wallet

Octovo – The Purist

The Purist is constructed of thin, high-quality leather and features a simple but efficient design.

I love the angled slots, which diminish bulkiness and make it easier to access the cards. Even when full, this wallet is still quite slim.

I’m not the biggest fan of the two-toned leather lining, but it’s not enough to sway my recommendation.

My only concern with this wallet is the outter leather. Shiny leathers, like this, tend to show every little mark or stain on them. If you’re a little rougher on your wallets, I’d probably go with the Bellroy.

I’d recommend getting their black and chestnut colors.

Folded Card Cases

I didn’t include these in the video because they’re a little more niche than a bi-fold wallet or regular card case since they fold like a wallet, but can’t hold much cash. I still like them a lot and some clients prefer them over the non-folding card cases, so I thought best to include them.

Louis Vuitton – Pocket Organizer

Buy the Louis Vuitton Pocket Organizer

With smooth, coated edges and the different interior pockets, my clients really love this wallet. I’ve even given them as gifts a few times. I think the design, pocket placement and textured leather really stands out and feels great in the hand. Just a warning, it’s a little thicker than the other card cases, so if you’re looking for super small and thin, you won’t get it with this one. It feels more like a wallet than a card case.

Buy the Louis Vuitton Pocket Organizer

Valextra – Folded Card Case

Buy the Valextra Folded Card Case

Just like with their bi-fold wallet and regular card case (below), the leather is awesome and the design so classic and thin that it’s hard not to love it. I especially like how they keep the logo very small and out of the way, unlike some other brands…

Buy the Valextra Folded Card Case

Coach – Card Wallet

Buy the Coach Card Wallet

If the other options are a little pricey, you will love this one. I love the textured leather and the construction is quite good. A lot of times, Coach misses the mark, but they nailed it with this card wallet.

Buy the Coach Card Wallet

Card Cases

These are for the guys who want the slimmest wallet-ish thing possible and don’t have the need to carry much cash. Or, as I’ll touch upon later, as a secondary, going-out wallet.

Valextra – Card Case

Buy the Valextra Card Case

Just like their bi-fold wallet. This card case is super luxurious, thin and well-constructed. There’s not much else to say, I actually like this one because it has 6 slots, so you won’t have to stack a lot of cards in it. Most other card cases have 3 or 4 slots so you’ll have to dig through your cards to find the right one.

Buy the Valextra Card Case

Bellroy – Micro Sleeve

Buy the Bellroy Micro Sleeve

If the Valextra isn’t your thing, this is a great alternative. Just like their bi-fold wallet, it’s a super durable, thin and features a unique and logical design.

The card slots with different orientations, make it’ easier to pull out your cards and squeeze the sides to expose the center pocket’s contents. I also love the curved edges since it’s easier to slip in and out of your pocket and not catch or snag on anything.

Just like with their Low Down wallet, though, I wish the stitching wasn’t so contrasting. I only like the black or blue steel colors because the other options are either two-toned or really loud.

Buy the Bellroy Micro Sleeve

Octovo – The Slice

Soft, supple leather and classy as hell. Unlike with their bi-fold wallet, I actually like the two-tone top pocket because it’s just a little nice surprise and doesn’t scream at you.

Black is the best color for this wallet, and just like with their bi-fold wallet, I question the durability of the leather if you’re rougher on your wallets, but I really, really like the clean and simple design.

Phone Wallet

If you’re looking for a wallet that holds you cards, cash and phone, these are for you. Let me warn you, though, they’re the opposite of slim wallets. If you wear suits, carry a bag often, or don’t mind carrying your wallet in your hand, these are right up your alley.

I’ve had clients explain to me the joy of carrying their phone in their wallets – where it takes a little more effort and time to get to their phones. They say it makes their actions more deliberate and less reactive and schizophrenic. It’s almost like an excuse to take their time. One client explained the opening/unzipping his phone wallet like a sort of ritual. Like rolling up your shirt sleeves or doing something methodically.

I looked long and hard for good ones and even though there’s a lot out there, I found most of them to be lacking in one major area or another.

Bellroy – Phone Pocket

Buy the Bellroy Phone Wallet

Like Bellroy’s bi-fold wallet and card case (above), the phone pocket is made from the same leather that is very scratch and blemish resistant with a buttery smooth zipper and an equally logical and well-thought out design. My clients who use this wallet really love it.

I love the pocket layout, where the phone fits in the main compartment and your cards fit in a bit of a floating divider, making everything easily accessible. It also has slots for extra SIM cards, small pens and a place to put your house key. They literally thought of everything.

They make two sizes – for larger and smaller phones. I only like the black, though, as the other colors have odd-colored zippers and pull tabs, and/or the color is just too loud and not befitting a proper gentleman.

Buy the Bellroy Phone Wallet

This is Ground – Stash, Phone Wallet

Buy ‘The Stash’ Phone Wallet

After scouring the web for months trying to find other great phone wallets, I was so happy to find This Is Ground. Turns out that they’re located less than 5 miles away from my office! I got to visit them and they showed me all their goods and I was very impressed.

If you don’t like the Bellroy Phone Pocket, then go for this one. It cuts out all the extra frills and gives you just the essentials. Which is not a bad thing at all. Some clients noted how they preferred how this one opens flat over the taco-style opening of the Bellroy.

The leather is so supple and nice to hold that it really sets itself apart. It’s not as scratch/blemish resistant as the Bellroy, but this wallet will age and mature with you and have a much nicer patina.

The only downside is that the zipper tends to stick a little for the first week or two. My clients were definitely spoiled after using the Bellroy, but they all said it smoothed out after “working it in”, so it’s a minor quibble.

I love the Smoke (black) and Cognac colors the most. The Cognac looks amazing in person. The Stash comes in small and large phone sizes, as well.

Buy ‘The Stash’ Phone Wallet

So which wallet(s) should you own?

For my clients, I normally recommend they get a bi-fold or phone wallet and then a card case for when they don’t need to carry as much – like when they’re going out for the night or to a premiere or after-party, where seeing pocket bulges is a big no-no.

For a guy that likes his phone and wallet separate and needs to carry a decent amount of cards/cash with him, I’d say get a bi-fold and get a card case for when you’re going out for the night or just don’t need to carry all your stuff with you.

If you want to carry as little with you as possible and hate added bulk, get a card case. But don’t delude yourself and cram 15 cards into a card case and still think it’ll be slim. If that’s the case, you should just get a bi-fold, as it’ll do a better job of distributing that bulk in your pocket.

If you’re a guy who likes to carry everything all together, or doesn’t want to sit on a chunk of leather and cards, then the phone wallets are for you.

I think a man should have a regular, everyday wallet that can be placed into a breast pocket in your blazer or suit jacket and some form of a slim wallet that can slide into a front or back pants pocket when you don’t need everything – like when you’re going out for the evening, etc.

Just like with keys, you don’t need to and shouldn’t have to carry everything with you at all times. Most men/my clients love to say “But what if I need something in the wallet?”

The argument quickly crumbles when I ask them:
“So you’re going out for drinks with your friends, and need your gym, library, membership cards in case you need to go work out while reading a book at 2am?”

Most men know what kind of night they’re going to have, so don’t pull that BS of needing your tactical wallet with you at all times.