We often talk about how important accessories are to your overall look and wardrobe. When done well, they add that extra 10% that pulls everything together and really lets your personality shine. We don’t recommend a ton of accessories but watches are one of the most important ones. It’s true that the watch you wear says a lot about you, whether you like it or not. That’s especially true when it comes to the opposite sex. Since you’re probably going to ask, no, it doesn’t matter AT ALL how expensive your watch is, let’s just get that straight. But that doesn’t mean watches aren’t something women care about.
Here are the reason why a man’s watch matters to women!
SHOWS SOMETHING ABOUT YOUR LIFESTYLE
Whether you’re wearing a Timex, Apple Watch, or a Rolex, the watch you wear will give a woman a few clues as to what your lifestyle is like, and that’s important when we are getting to know you. Maybe you’re a sporty guy and you’re into a G-Shock. Or, you’re more of a tech guy and an Apple watch is your vibe. Either way, it lets women know a bit about who you are.
SHOWS YOU PAY ATTENTION TO THE DETAILS
Like with all of your wardrobe, the details matter and women notice the details. From the fit of your clothes to your haircut, each small component combines to form an important part of the whole. Watches are no different. The right watch and style choices on your wrist show you care about the right details.
SHOWS HOW CULTURED YOU ARE OR AREN’T
Maybe you think watches are redundant since you have a phone, sure, we get that. But, going that extra step is going to add another layer to your style and show that you’re about more than just the absolute bare minimum, and that’s definitely really sexy. But, it’s important to consider what you’re wearing and when just like your shoe choice. You wouldn’t wear Jordans to a wedding so you should consider what watch choices you’re making too.
INDICATES WHERE YOU MIGHT BE IN LIFE
No matter where you are on your journey, personal or style-wise, your watch choice is a big indicator of where you are and where you are going. Like we said before, women (well, the right women anyway) aren’t concerned with how fancy or expensive your watch is, but knowing where you’re at and where you’re going is important.
After I released my Top 5 Fall Essentials article/video, I received a lot of questions about how to style different washes of denim jackets. I heard you loud and clear, so here’s some of my favorite ways to style them.
Light Wash
To avoid looking like you’re wearing a Canadian tuxedo, wear light wash denim jackets with chinos. You can pretty much get away with any color, but my favorites are navy, green, brown, and burgundy. My classic go-to formula is a t-shirt, chinos, and chukka boots. Crewneck sweaters or oxford button-downs are also good options as well.
$90 – Levi’s denim jacket (in Queen) – You can never go wrong with this iconic denim jacket. Go with the next size down for this one because it’s not as fitted as the AllSaints one above and you always want a snug fit in the arms and body for all your denim jackets.
Dark Wash
If you only have the budget for one denim jacket, a dark washed one is what I’d choose. I love how dark the wash is because it’s easier to dress it up or down and it also has a slimming effect. I would avoid wearing jeans with a dark wash jacket unless they’re black because I don’t think it looks great and typically most men don’t know how to pair different washes of denim well. You can never go wrong with a pair of chinos and a crewneck t-shirt or sweater. If you want to dress the jacket up more, than pair it with some wool trousers and a collared shirt like I did in my fall accessory essentials article/video.
Tall, dark, and handsome is how I describe the outfit you’ll be wearing with a grey (or black) denim jacket. Keep it all black – t-shirt, jeans, and boots. You can also go with a white t-shirt but I love how sharp an all black outfit looks with a gray denim jacket adding that perfect pop of monochrome color – it’s especially perfect for a night out.
Since Fall is upon us, I wanted to do an update and supplement to my Men’s Fall & Winter Essentials series. So don’t think of this as a replacement for the series, think of it as a next-tier type of video and article. Enjoy!
1 & 2. Denim Jacket + Chino Pants
My first pick for the season is a denim jacket. It’s perfect for this time of year and works equally well during Springtime, too. Not only does it look good on every body type, but you can layer the heck out of them depending on how cool or warm the weather is. I recommend my go-to styling formula for denim jackets: wear with a t-shirt or crewneck sweater and a pair of chinos and boots.
My second choice are olive, tan and burgandy chino pants. Some of my favorite colors for the season are olive green, brown, and burgundy, which you can easily wear with your other casual jackets and sportcoats.
$70 – Levi’s trucker jacket – You can never go wrong with the brand’s iconic denim jacket. $225 – Rag & Bone slim fit chinos – I’m a huge fan of their chinos because they use a stiffer fabric that’s lays really nicely along the ankles and is super flattering on all shapes and sizes, especially if you’re a hefty fella.
3 & 4. Patterned Sweater & Boots
My third Fall Essential is a patterned sweater. Hopefully, you’ve already got the basic, plain sweaters, so now it’s time to add one that has a subtle pattern because it’s an easy way to add a visually interesting element to your outfits. Also, a pattern helps draw attention away from the torso which is especially beneficial if you’re a slim or husky guy.
My fourth Fall Essential is a pair of boots. You can go with leather or suede, dress or casual boots, but for me, I’m all about the taupe suede boots featured below. These are my hands-down favorite for the season because the color is the perfect dark brownish-grey so they can be used in place of brown or black boots.
$89 – Banana Republic wool birdseye sweater – I’m so impressed with not only the fit, but by the superior wool you can get for under $100. The brand sourced the wool from Zegna’s factory, which is always high quality and can easily set you back $600+. $178 – Banana Republic suede work boot
5. Chambray Shirt
My final pick for the season is a chambray shirt. It looks great on its own or layered underneath a cardigan or jacket. I recommend wearing yours with chinos or wool trousers.
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.
There’s 3 types of Fall and Winter Boots for men that I love for this time of year – Dress, casual and chukka boots.
The reason I love boots for Fall/Winter is that they go so well with jeans, wool trousers and fall/winter suits. They also do a great job of keeping your feet warm and protected from the elements – while looking classy and more refined than a pair of hiking boots or something that’s just a straight utility item.
Now, if you live in an area with a good amount of snow or rain, then you should probably have specialty boots for the crazy days, too, but those are outside the scope of this article.
The difference between dress and casual boots
Dress boots are more formal and can be worn with a suit or wool trousers. They have a sleeker profile, usually leather or dainite soles, and are made out of shinier calf skin, as opposed to cow hide. Dress boots are like dress shoes with a shaft, basically.
Casual boots usually have more room in the toe box, the leather is usually a thicker cowhide that is more matte, and the soles usually have lugs on them. They look a little less dressy and sophisticated, which is why they look so great with jeans, but you can also still wear them with wool trousers.
My Requirements for a good Fall/Winter Boot
These items apply to all the types of boots – dress, casual and chukka boots:
1. A slim profile and not chunky
Timberlands (right) are the exact opposite of what I’m looking for in a good boot. You want a nice, rounded toe box with a slim profile as well as sole like the image below.
2. Plain, Cap Toe or Broguing
I like all 3 of them, but just like with my dress shoes, I’ll always prefer a plain or cap-toe, but broguing is also acceptable. Broguing is not really my preference because I think a lot of guys overdo it with the broguing, burnished toes, etc. Too much can easily look gaudy if you’ve got too much going on in your outfit.
3. Lugged, Dainite or Rubber soles
These will give great grip in any type of weather. A normal dress boot has smooth leather on the bottom and you will slip and slide like crazy in wet weather. If you’re not in a climate with rain/snow, then you can go with straight leather bottoms typically found on most dress boots, but I see no reason to do that when any rubber bottom aside from lugged will look very similar with the extra benefit of additional traction.
4. Be brown or black leather
Go with nice dark chocolate or walnut brown first, then get black if you don’t have them already. Brown is a great fall/winter color and is easier to wear with casual AND more formal outfits. But be careful about getting a really specific brown color, like oxblood. As I’ve said in my other shoe videos, it’s a great color but doesn’t compliment a lot of outfits, so get that color once you’ve got these basics down.
And please, whatever you do, don’t get those terrible boots that are already worn in. It’s much better for you to wear them in yourself and really personalize their look to your actual lifestyle.
5. NOT be Suede
For Fall and Winter boots, suede is the last material you should consider, unless you live in a dry climate like Southern California where it rains maybe 3 or 4 times a year. Otherwise, they’ll get screwed up very quickly with any amount of rain or snow. I don’t care how much scotch guard you use, nothing can stand up to that much abuse. So save the suede shoes for spring, please.
Can I wear boots with a suit?
Yes, but only when these 2 conditions are met:
You’re wearing a heavier wool or tweed suit. For a visually heavy item like boots, you should understand fabric weights and pairing them with similar items. Even straight up dress boots can look odd with lighter weight wool suits. Make sure the wool is atlas 12oz thick. The easiest way to tell what a heavy wool suit feels like in person, is it should be as thick as a wool sweater (not as soft, though!)
Your pants are hemmed to have no break. The hem of your pants will look sloppy and bunched at the ankle, otherwise. You can technically cuff the hem of your suit pants to do this, but if they’re super long, it’ll never look quite right. So I usually just get the pants hemmed to no break for this. But that means you can’t wear this suit with anything but boots now…unless you have your tailor let out the hem when the seasons change.
How To Tie Your Boots
Check out my shoe and boot tying video for how to tie your shoelaces properly.
Watches are one of the few pieces of jewelry that any man can wear that is universally acceptable. Other jewelry like rings, earrings, necklaces and bracelets will have their detractors (myself included).
So for that reason alone, a watch is an accessory that every man should have. From a practical perspective, they are also nice for telling the date and time. But obviously not as required now that we’re carrying smartphones around with us all day long.
Just like I discussed in the series intro, there’s something amazing about owning a finely crafted piece of history and engineering perfection.
Whether you’re a watch guy or not, I think any self-respecting man should own a watch or two.
Before I get into the exact watches you should own, let me first answer the most common questions I get from clients, readers and viewers about watches:
What type of watch to wear with what outfits?
Suit = Dress Watch – you should never, ever wear a diving/chronograph/sport watch or anything but a leather or other hide strap with a suit. It drives me crazy when I see metal bracelets or nato straps with suits because they’re so casual in nature and they take away from the formality of a suit. It’s a SUPER amateur move.
Business Casual or casual outfits – Dress watch or Sport watch with a metal bracelet, leather/nato/rubber band. You can also wear a dress watch with them, but it depends on how “polished” your casual outfit is. If you’re in shorts and flip flops, that might not look right with a dress watch.
How to Match a Watch To Your Outfit
It’s pretty simple. If you’re wearing:
A suit with black dress shoes and belt. You should be wearing a dress watch with a black leather strap.
A Suit with Brown dress shoes and belt. You should be wearing a dress watch with a brown leather strap.
Anything outside of a suit, even if you’re wearing dress shoes, you can wear any type of watch you’d like – that includes dress watches as well as any sport, chrono, diver, pilot, etc. type of watches.
What size should your watch be?
If you have a smaller wrist, around 6″, then go with a 40mm or smaller.
If you have average to a wider wrist, around 7″ or bigger, then go with a 40 to 44mm sized watch.
Most older watches, including Rolex’s diving watches, were 38mm or less, but they’ve since shifted to 40mm to follow the trend of larger watches now.
Traditionally, dress watches were made to be smaller and fit under your shirt cuffs, while diving or chronograph watches are bigger so they’re easer to read while doing the activities they were designed for.
It’s really up to your personal preference. I’m a little new school in that I think dress watches don’t need to be tiny – my favorite IWC dress watch (below) is very large for a dress watch, but I still love it. Unless your wrists are extremely small, then any size between 36 and 44mm will be fine. Which is fortunate because almost all watches fall within these sizes anyways. It’s when you get into vintage watches that the sizes tend to be smaller. So if you prefer a smaller watch, then vintage may be right for you.
How Many Watches Should You Own?
To cover all your bases, you should own 2 to 3 watches. You can absolutely get away with owning only one (which I’ll discuss shortly), but 2 or 3 different types of watches will cover you for all the outfits and scenarios you’ll encounter. A lot of my clients who are into watches own usually double or triple that amount, but we’re talking about the barest of essentials right now and anything else would be a speciality or just not used as much.
What Watches Should You Own?
1. Silver Dress Watch with a Black Leather Strap
Here’s the basics of what this watch should be. If you own one watch, this should be it. That way it’ll cover you for the most scenarios. You’ll also need a brown leather band to swap out as your outfit accessories dictate according to the matching rules I discussed earlier. So scroll to the bottom to check out my favorite band/strap site to get your extra straps.
Your black leather strapped watch should have the following features:
Silver Case
You want a silver case because, just like with the hardware on your belts, it’ll match with everything. If you were to get a watch with a gold or black case and black leather band, it won’t match as well or be too sporty to complement the rest of your essential wardrobe items.
As for the size of the case, that’ll depend on your preference and what looks best on you, but a classic dress watch is supposed to be very thin and small (sub 40MM, usually), but I’m a little new school in this regard and don’t mind a taller or larger case, something like the 44mm IWC cases is fine, but right on the edge, for me. Honestly, go smaller if you have a small wrist, and bigger, if you have a wider wrist.
White Dial
The dial of your watch should be white because it’ll match perfectly with everything you could possibly throw at it. Black, blue, skeleton or other dials won’t match as well or will come off as too sporty or gaudy. I just think of all the sleezy salesman guys wearing their Movado watches at the bar after work – bleh.
Black Leather Strap
You can also use a leather alternative or other hide – kangaroo, ostrich, alligator, etc. The one thing you should never do is wear a nato or rubber strap with a suit. If I can be blunt – it looks like shit and is an amateur move. The quickest way to look like a teenager or style blogger is to wear a nato or rubber strap with every outfit. Those should be reserved for casual outfits only.
In regard to the stitching on the strap, I’ll forever dislike contrasting stitching, just like I do on wallets, so ideally, the stitching should match the color of the strap.
Subdials or complications
I’m a little new school in that I don’t believe a dress watch needs to have the cleanest dial possible. I don’t mind a few subdials or complications like a power reserve, subdial seconds, moon phase or month/day date. Just don’t go crazy and use a chronograph with a leather strap as a dress watch, please.
2. Silver or Gold Dress watch with a brown leather strap
The requirements for your brown leather-strapped dress watch are nearly identical to the black leather strapped dress watch above – with one major exception:
This is the one time when a gold case is acceptable because the dominant color of the accessories you’d be matching with would be brown, regardless of the hardware color of your belt. I’d still prefer a silver case if given the choice, but a gold case would work just as well.
If you have the budget for only one watch, or only want to own one dress watch, then make sure to get a brown band to swap out with your silver cased watch as your outfit accessories dictate. It’s a little bit of a pain, but not so much that this isn’t an option. Changing watch straps is quite easy and I have a great place to get really nice straps for cheap.
These watches are often called Sport watches, as well. You want this type of watch to round out your collection because it goes with any outfit from business casual on down. Unless you’re wearing a very sharp casual outfit, you shouldn’t be wearing a dress watch. That’s when a sport watch comes in to play. And please, for the love of all that is holy, please don’t wear your sport watch with a suit. I immediately know a guy doesn’t know much about looking good when I see a sport watch with a suit.
Here’s the details of what I look for in a good sport watch.
Black or Blue Dial
If I had my choice, I would choose a black or blue dial, with a slight edge to blue, as long as it’s more navy like Omega’s Speedmaster in Titanium (below) and not a royal blue like the Rolex Submariner in 16k white gold. The latter is just way too loud.
Silver Metal Bracelet
There’s nothing better for casual outfits than a diving or chronograph watch with a metal bracelet – in either titanium or stainless steel. Just like in the dress watches above, I prefer these materials and colors over a black or gold bracelet because it goes with everything and all the hardware on your belts, tie bars, etc. I also really love to see the metal bracelets swapped out for leather, rubber, perlon or nato straps, as well, but metal bracelets are a necessity for any sport watch – so you want to make sure it comes with that, first. For different watch straps, scroll down to the bottom of this article for my favorite place to get additional straps.
First and foremost, there’s no substitute for OEM straps or bands. But a really close second is my favorite aftermarket strap/band site – CheapestNatoStraps.com. Don’t let the name fool you, they’re neither cheap, in terms of quality, and they make a lot more than nato straps. I’ve been swapping out watch straps and bands for clients for a long time now and this is the only place I go for aftermarket straps.
I talked to the owner, Sofie, and she was kind enough to offer you an additional 10% off your purchase if you use offer code: AshleyWeston
Special Thanks
A big thanks to reader/viewer Travis and the team over at www.Horobox.com for letting me bounce thoughts and ideas off them and providing their expertise and insight for this story. Definitely check them out!
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