Men’s Winter Style Do’s and Don’ts | Men’s Winter Style Tips

Winter can be a tough time for your personal style. Cold weather and the elements can lull you into just giving up, but don’t do it! These few simple tips can keep you looking sharp and feeling great, no matter how cold it gets! For more tips, make sure to check out our Fall/Winter Essentials Series!

Here are our Winter Style Do’s and Don’ts!

Winter Style Do’s

Do Add Some Colorful Jewel-toned Accessories

The right hats, scarves, and gloves are crucial for warmth and style. They’re also a great opportunity to add some color and pattern to brighten up your look. Colors like emerald green, a mustardy yellow, dark purples, reds, and blues are all easy to incorporate into your winter wardrobe and pack a stylish punch of color.

Picks:

Scarf 1

Scarf 2

Scarf 3

Hat 1

Hat 2

Hat 3

Gloves 1

Gloves 2

Gloves 3

 

Do Invest In Quality Outerwear

We talk a lot about where and when to invest, and outside of dress shoes & boots, outerwear is the other major area we really recommend investing in. You get what you pay for and with the right investment, a high-quality coat, peacoat, or jacket will last for years to come, keep you warm, and have you looking stylish.

Picks:

Overcoat

Overcoat 2

Parka

Puffer Parka

Parka 2

Peacoat

Peacoat 2

 

Do Get The Right thermals

There are many great brands offering very thin/lightweight thermals that’ll layer comfortably underneath your clothes and keep you warm. The key is to get a trim fit, that way they’ll lay flat and layer easily under everything from jeans to suits. Our pick below is light, warm and you can wear these as a base layer underneath your clothes or on their own as a long sleeve shirt.

Thermals Pick

 

Winter Style Don’ts

Don’t Neglect Your Skin

You may not think so, but cold-weather skincare is just as important as warm weather skincare. The cold, dry weather can be incredibly harsh on your skin and strip away it’s protection, so it’s super important to cleanse and moisturize properly and stay hydrated. There’s nothing more distracting and unattractive than dry, dull skin.

Luckily, our friends at Geologie have you covered. Geologie puts together a simple routine formulated for daily use. The products are personalized to your skin’s needs and work great for every skin type. We tested out their set that comes with 4 different products:  Everyday Face Wash, Vital Morning Face Cream w/ SPF, Repairing Night Cream & Nourishing Eye Cream. It even includes 2 bottles of face wash, one for your sink and one for your shower or to take with you to the gym. Plus, just for our readers and viewers, you can get 30% off your purchase with code Ashley30! Shop here and enter the code at checkout.

 

Don’t Forget To Layer

We talked about it for Fall, and it’s just as applicable in Winter.  Proper layering can help you regulate your temperature and look stylish no matter how cold it is, making sure you’re comfortable going from the cold outside to warm inside (subway, office, etc.).

 

Don’t Forget To Winterize your boots

Boots are essential footwear for Winter (our go-to picks for this year are right here) and the right pair can look amazing and last a long time. But, you’ve got to prepare them with the right leather treatments to keep them from getting ruined in the inclement weather.

Boot Treatment Kit

Why A Man’s Watch Matters To Women

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.

Are Smartwatches Stylish or Fashionable?

In this week’s 2 Minute Tuesday, we’re talking about smartwatches. Now a pretty common men’s accessory, there are a bunch of different styles and brands. But, are they stylish? What’s the right way to wear them?

Don’t forget to check out our in-depth guide about men’s watches for all of our watch style tips and picks.

Smartwatch Style Tips

  1. Only wear with casual and business casual – The look and style of a smartwatch is really only suited to your casual wardrobe. So, if you’re going to be dressing more formally in a suit or blazer look, opt for a more formal style of watch.
  2. Mix up your look – The interchangeable bands offer you a great opportunity to mix up the look and style of your smartwatch, so don’t be afraid to experiment with different colors and leathers.

Holiday Gifts Under $50 For Him

This season, I wanted to break up my annual gift guides by price and gender, so in this one, I want to talk about the gifts under $50 for the various men in your life. 

Keyring Multi-Tool

Every man will find this handy, regardless of his age or occupation. I like it because it easily fits on a keyring and is super convenient.

$35 – Leatherman Squirt PS4

Pocket Pen

Well designed, pocketable, and something most men don’t think about it but use more often than they’d think.

$20 – Fisher Space Pen

 

Cigar Pack

A humidity sealed pack with two cigars, a cutter, and matches for the aficionado, or those who’ve yet to be initiated into the cigar world. You can pick these up as either single purchases, or a part of a monthly subscription. Dorian has spoken to the CEO a few times and has sampled a few of their packages and says they’re top-notch.

$30 – Cigar Pack (2 cigars)

 

Leather Keryring

This unique leather keyring will keep up to 7 keys all organized and silent within its cowhide leather sheath in your pocket. Like I mentioned in my Accessory Essentials Series, use quality items and you’ll thank yourself (or the man you give this to will thank you, hopefully).

$45 – Orbitkey Keyring

 

Nose & Ear Hair Trimmer

It’s one of those things that most men don’t think of buying for themselves but will use way more often when they actually have it in their grooming kit. It seems weird, but a lot of clients have commented about it being one of the best sleeper-hit style gifts they’ve ever received.

$20 – Panasonic Trimmer

 

Classic Watch

Beautiful, classic styling and a great price – you can’t go wrong. I’ve covered this and many, many other watches in my best men’s watches guide.

$35 – Timex Weekender Watch

 

Braided Charging Cables

Charging cables can be a boring necessity, or they can be a classy addition to a man’s Everyday Carry. I’d suggest getting a 10ft cable – the extra length comes in way more handy than you’d think.

$10 to $50 – Native Union

 

High Quality Socks

One might think this is a boring choice, but if you haven’t tried the best men’s socks yourself, you’d be dead wrong. Give the gift of amazing comfort and a lifetime warranty with these awesome socks.

$10 to $40 – Darn Tough Socks

 

Coffee & Espresso Maker

Hailed as one of the best ways to make a single serving coffee, I’ve gifted this to quite a few people who are into coffee and it’s been a success every time.

$25 – Aeropress Coffee & Espresso Maker

Men’s Fall & Winter Accessories 2017

In this article and video, I wanted to show and discuss some of my favorite accessories for the Fall & Winter Seasons. Also, please be sure to not miss out on my whole series dedicated to the best men’s Fall & Winter Essentials.

 

Watch Straps

Fall and winter is a great time of year to change out the straps of your watches for more appropriate colors for the season. As for materials, I don’t have a preference, but leather, perlon and suede are some of my favorites. The best colors for this time are always going to be:

  • Browns
  • Oranges
  • Burgundy
  • Taupe/Gray/Green

The pictured straps, as well as many others types and styles are available at my favorite site for reasonably-priced straps: CheapestNatoStraps.com

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

Suede Belts

Since you’ll be wearing heavier fabrics during this time of year, it’s time to bring out the suede belts to add a more visual texture to your outfits to compliment them. I prefer a dark brown or gray color this time of year and the below options have these choices available.

$128 – Brooks Brother Suede Belt – the best color for the time of year.
$80 – Torino Suede Belts (Various colors – I like espresso & navy)
$25 – H&M Suede Belt

Wool Ties & Pocket Squares

Wool ties and wool knit ties and pocket squares compliment the textures you’ll be wearing this season. For how to wear them, watch the video at the top. Just know that you’ll never go wrong with the rule: Whatever item has a pattern (tie or pocket square), make sure the other item isn’t patterned. So if you’re wearing a patterned tie, wear a plain pocket square with a similar colored tipping.

The colors I love this time of year are:

  • Browns
  • Oranges
  • Burgundy
  • Grays
  • Greens

 

I’ve talked at length about my favorite pocket squares and how to wear them, so see my wool ties & pocket squares video/article for details.

Wool Knit Caps

They’re great this time of year to keep your head warm and they can look good  but remain functional when paired with some of your  casual jackets or even heavier Winter jackets.

Gray, Blue and Black caps are my favorite colors because they go with everything, but you can certainly mix it up with other colors, if you prefer. There’s one caveat when wearing them, though.

$90 – A.P.C. Wool Knit Cap – Multiple Colors
$10 – H&M Rib-Knit Cap

Leather Gloves

Leather looks great this time of year and help elevate your appearance by adding a sophisticated touch, while keeping your hands warm. Black or brown are easiest to wear, so I say just get one or both of those colors.

$30 to $40 – H&M Leather Gloves
$100 to $600 – Various Quality Brands @ Mr. Porter

Scarves

Keeping your neck warm should be a priority, but why not have your scarf also look good? As far as colors and patterns are concerned, I honestly view them like men’s socks, where you can definitely go crazy with them, so if you think a plain color is boring, go with some patterns. Generally, you want to go with the same general color palette of the season – so blue, gray, black, brown, orange, burgundy and green all look great this time of year.

As for materials, I don’t think it matters much, it just depends on what you prefer. I love a good wool or cashmere scarf, but a cotton one is also good, depending on how thick and warm you want yours to be. But, there may be a reason to avoid certain materials or colors.

I’ve discussed how to tie men’s scarves at length so check that out, too.

$10 to $100 – H&M Scarves – they make some of my favorite budget friendly scarves.
$15 to $50 – Uniqlo Scarves – also great budget-friendly options.
$50 to $500 – Mr. Porter has a great selection of many high quality scarves.

Best Men’s Watches

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.

The Best Dress Watches

IWC Portugieser and Patek Philippe

$12,000 – IWC Portugieser Automatic
$20,000 – Patek Philippe Calatrava White Dial

 

A lot of these watches come with black or brown straps.

$65.00 – Stuhrling Original Ascot II
$90.00 – Bulova Classic Dress Watch
$200 – Bulova Dress Watch
$220 – Tissot T-Classic Tradition
$230 – Mondaine Swiss Railways Evo 
$260 – Graf Zeppelin Hindenburg
$300 – Orient 2nd Generation Bambino
$520 – Junkers Bauhaus
$530 – Hamilton Intra-Matic Silver Dial
$650 – Tissot Heritage Visodate Automatic
$650 – Frederique Constant Classics Index Automatic
$1,100 – Junghans Max Bill Chronoschope
$1,600 – Tag Heuer Carrera Calibre 5 Automatic
$1,800 – Junghans Max Bill Automatic
$2,500 – Cartier Tank Solo  
$2,500 – Montblanc Heritage Chronométrie Automatic
$2,780 – Nomos Tangente 38 Datum
$3,600 – Omega De Ville Prestige Co-Axial 39.5 MM
$3,700 – Nomos Minimatik
$6,000 – Cartier Ballon Bleu de Cartier
$7,600 – IWC Portugieser Chronograph
$12,200 – Jaeger Le-Coultre Reverso Classic Large Duo Face
$15,000 – Omega De Ville Trésor Omega Master Co-Axial 40 MM

3. A Chronograph or Diving Watch

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.

The Best Sport Watches

omega-rolex-ashley-weston

$11,000 – Omega Speedmaster – Moonwatch Omega Co-Axial Chronograph 44.25 MM
A quick note about the Speedster – the blue is much, much darker in person. The official images do it no justice.
$8,000 – Rolex Oyster Perpetual Submariner Date

$75.00 – Casio Super Illuminator Diver
$80.00 – Stuhlring Aquadiver
$100 – Parnis p101506 Mechanical
$125 – Fanmis Submariner
$150 – $200 – Seiko 5 Sports Automatic (also in a dark blue version)
$400 – Orient Mako USA II (has blue & black options)
$500 – Steinhart Ocean 1 Black
$450 – Tissot V8 Quartz Chronograph
$450 – Borealis Bull Shark
$550 – Seiko Prospex Kinetic Dive Watch
$660 – Certina C024.447.11.081.00
$700 – Hamilton Seaview Day Date Quartz Blue Dial (Also make blue dial & automatic versions)
$700 – Victorinix Maverick Stainless Steel Bracelet Watch
$800 – Longines Hydro Conquest
$2,000 – Tag Heuer Aquaracer Calibre 5
$4,000 – Tudor Pelagos
$6,000 – Omega Seamaster 300 Omega Master Co-Axial 
$6,000 – Omega Speedmaster Moonwatch Omega Co-Axial Chronography
$7,850 – IWC Aquatimer Chronograph
$15,000 – Rolex Daytona

The Best Watch Straps and Bands

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!

The #AskAW Show: Episode 02

Have a question you’d like me to answer? Ask in the comments of this youtube video or send me an email.

Show Notes & Links

Q: I’d like to find a good pair of suede Chukka Boots, but I’ve got big feet – Size 15, can you help?

Allen Edmonds - Dundee Suede

Allen Edmonds – Dundee Suede

 

Q: What can I wear with my blue suede wingtips?

Dark wash jeans 

 

Q: How can I dress nicely in really warm weather?

Polo Shirts

 

Linen Button Up Shirt

 

Chino Pant

 

Shoes

 

Q: What watches would you recommend for a guy with skinny wrists who wants a brown band?

 

Q: What do you think about the proportions of this jacket?

Fashionbeans.com story I commented on.