Thanks to Jose for joining us for this video and thanks to IWC, one of our favorite watch brands of all time, for helping make this video happen!
Have questions? Curious what others think?
Join us in the comments section of the video above.
16. White Pocket Square
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.
15. Silver Tie Bar
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.
14. Solid Black and Navy Tie
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.
13. Dress Socks
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.
11. Baseball Hat
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.
10. Black and Brown Oxford or Derby Shoes
9. Black and Brown Dress Belts
Since you’re going to own dress shoes, you absolutely need to match your leather belt to your shoes.
8. Weekender Bag
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.
$965 – Frank Clegg Signature Travel Duffle (in black, chocolate or chesnut)
$800 – Killspencer Weekender 3.0 (in black leather or charcoal grey leather)
$115 – Everlane ‘The Dipped Weekender’ (in black/black, navy/black or reverse denim/black)
7. Dopp Kit
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.
6. Backpack or Briefcase with Detachable Strap
5. Casual or Dress Watch
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.
4. White Low Top Sneakers
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.
3. Boxer Briefs
All women find boxer briefs, specifically darker colors, so sexy on a man. And all men should be wearing them. Period.
2. Black and Brown Casual Leather Belts
1. A Quality Wallet
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.
Why Own a dopp kit or Toiletry Bag?
The reasons you need one are many, but allow me to give a woman’s perspective and reasons for a moment.
In dating and life, we’re always looking at the smaller, subtle details to learn a little more about a person. We’re more sensitive to these subtleties and when a client asks why a dopp kit is important to own, I tell him that when a woman sees a man is organized and respects himself enough to have nice things, it makes us feel validated, like we found “a good one” because this small detail supports a notion that he probably has his life together and is a potentially good mate. It’s a very visceral, biological reaction that we get.
I often say it’s a similar thought to the old saying, “A messy bed equals a messy head” meaning that the way someone’s bed looks gives you some insight into their mental state.
On top of that, it’ll make traveling or going to the gym that much quicker and easier for you by keeping all your toiletries nice and organized. It’ll also help protect your clothing and luggage if you ever have any toiletries leak or spill.
What should a Dopp Kit do?
- It should carry your toiletries, of course.
- You also want it to be easy to use. There’s a lot of dopp kits out there, but my favorites are always the zip top style (see my choices below for examples) because the other styles aren’t as easy to pack or access items without having to move other things around. I had a client take a big chunk of out his finger with his razor while carelessly going through his non-top loading Dopp Kit and that’s what started me on the quest to find the perfect one. The next best alternative is the wide-mouth style (see the Shinola example below), but I find these tend to sacrifice some storage space to have the hinge. Even the original Dopp kit does this. My example below is the best I found with a hinge because it takes up less space than similar bags.
- The last thing your Dopp Kit should do is last for the rest of your life. Unless things change dramatically over the course of your life, this should be the last one you ever buy. So if you’re hesitant because of pricing, don’t be. The cost per year will be so small that it’s absolutely worth it.
What Should it be made of?
Like with all the other bags I recommend in this series, I think there’s just no substitute for leather. It doesn’t stain as easily, and those stains will happen much quicker than your other items since it’s close to a lot of water and toothpaste, etc. Also, leather just looks much classier. Cloth or plastic alternatives are okay, but they just don’t compare, in my eyes.
What color should it be?
Just like all your other accessories, black or brown are my favorites. You can definitely go with other colors since not many people will see it, but I always stick to the classics here. Do you need to match it to your weekender bag? I would default to yes, because why not? But if you really like a brown dopp kitt and own a black weekender bag, then I don’t see an issue with that.
The Best Dopp Kits or Toiletry Bags
Jack Spade Leather Dopp Kit
It is my absolute favorite and one I’ve gifted to a lot of family and friends over the years. It’s simple, not too big or small, and has my favorite zip top design, so it’s very easy to access your items. I like just the simple pocket on the top, as well as the small side pockets for items that can fit there. Like all dopp kits should have, it of course has a waterproof lining, so if anything spills, it won’t be a total disaster for the items in your luggage.
I’d say that this one is perfect in every way.
Shinola Travel Kit
This is one of the few traditional style dopp kits that I could find with a hinge top opening, which allows you to access the entire compartment. Shinola’s leather is really damn good and even though it only comes in black, if you prefer this shape over the zip top style, this one is definitely for you.
This Is Ground Tech Dopp Kit
While these are not technically a toiletry bag or dopp kit, they call it their “Tech Dopp Kit”, I’ve found the multiple size opens and construction as close to perfect as possible. The only thing it’s missing is the waterproof lining, but as long as you’re relatively careful with packing your liquids, it wouldn’t call this a deal breaker.
I show the different sizes in the video at the top of this page, but I would recommend you get their “regular” size since it’s comparable to your average dopp kit’s size. But if you want something smaller or bigger, I think it’s great that they have those options available, too.
Definitely get it monogramed for that little extra special touch!
KILLSPENCER Dopp/Folio 2.0
Like all their products, it has a nice, supple leather with a great, tactical edge. I like it a lot because it has a unique look compared to all the other dopp kits out there and the inside is fully waterproof, so if anything spills, it won’t be a total disaster. While not a requirement, when you’re not using it as a dopp kit, it can also double as a folio by squishing it down a little bit. I thought this was a nice touch, but I don’t know how often it would be used like this. It’s definitely on the larger side of the spectrum, so if you’re looking for a larger dopp, this one is right for you.
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
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!
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.
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
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
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
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
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
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.
These are the weekender bags that just missed the mark for one reason or another.
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
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
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
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.