Winter can be a tough time for your personal style, plus the weather and elements require special attention for your wardrobe and, more importantly, your accessories. That said, the right winter accessories will bring both function and personality to your wardrobe. It doesn’t all have to be about keeping warm (though that’s definitely important), it’s a great opportunity to add some extra style to whatever you’re wearing. For more basic tips, make sure to check out all of our Winter Essentials and our article on Winter Style Do’s and Don’ts
Here are our picks for the Men’s Winter Accessories That Every Man Should Own!
Cashmere / Wool Knit Hat
A must when it’s freezing. Go for a thicker rib knit and try cashmere for a luxurious touch that’s soft, light, and warm. Don’t be afraid to try a pop of color here too!
The perfect time to add some color or pattern into the mix. Just a hint of it peeking out from under a coat is a sharp, stylish look. Cashmere is a great option here too, it’s very light and warm.
We’re not talking about thick ski-style gloves, but something lighter but still warm. Look for knit versions in wool or cashmere or lined leather options for a sharp touch (especially if you dress up often).
Add in a thin watch that toes the line between dressy and casual so you can dress it up or down. Layered and formal outfits need a watch that’s not big and bulky. Wearing a big, sporty watch with dressier looks can just throw off the proportions. Luckily our friends at Nove watches have the perfect styles. Their watches are high-quality, Swiss-made, and come in a variety of slim styles that work well with a range of looks. Plus, we’ve got a special deal for you guys. Use offer code AW20 for 20% off your purchase.
Merino wool has incredible technical properties (warm, lightweight and dries quickly) and there are great options out there that are lightweight, warm, and stylish.
We discussed in our Winter Do’s and Don’ts, and the right pair won’t be bulky or too hot and can easily layer underneath both casual and dressy clothes. We really like our go-to pick below because they are very light, warm, and won’t break the bank.
Nobody likes the look of dull, dry skin and the cold, dry air can be brutal on your hands and face so take extra care to moisturize properly. The right products and a solid morning routine and evening grooming routine will really help keep your skin looking great during the winter.
Proper boots for the winter are crucial and if you’re dealing with a lot of rain and snow you want to make sure your boots are protected and have a rubber sole for traction and durability. Some of our picks below have a Dainite sole which is the gold standard in terms of protection and grip in wet, snowy conditions.
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.
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.
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.
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.
Accessories may seem like a small thing but they’re one of my favorite ways to mix up your look and add some extra personality in a very affordable way. Whether you’re adding a new tie to your rotation, trying out a new watch or piece of jewelry, or bringing in something more utilitarian like a key holder, these extra touches to your personal style will go a long way.
With that in mind, here are my favorite men’s accessories under $100!
A tie bar is great because it’s both utilitarian and stylish. It’s a small touch but you can mix and match with different colors, finishes, and styles to add just a bit of personality to your tie game.
Speaking of ties, I love the texture and look of a knit tie because it’s just a bit different from the norm. Plus, because of look and design, knit ties crossover to more casual looks very easily, so try pairing them with a blazer and denim or an oxford and chinos.
A silver cuff is a great place to start with men’s jewelry because it’s simple and not too over-the-top. Just make sure you keep it low key and only wear one piece of jewelry at a time.
I love the colored clear-framed sunglass styles that are happening right now. They’re definitely different enough to add something new to your look but not so bold as to be distracting. Don’t forget to check out my guide to finding the right frame for your face shape!
As I mentioned above, clear-framed sunglasses are my favorite type of eyewear right now. Stick with a classic frame shape and you’ll hit just the right balance of modern and timeless.
Since I’m sure some of you have that bulky, disorganized key ring, I recommend this key holder as a simple, smart way to keep your keys organized in a stylish way.
Just like the key holder above, Bellroy has a knack for making stylish leather goods that are the perfect mix of minimal design and high-quality materials. Their Low Down wallet is a great pared-down choice.
Finding a phone case that’s both classy and protective is tough but Elago really nails it. They’re remarkably slim and minimal but still offer a great fit and protection, no matter what type of phone you have.
Despite its name, the Times Weekender is the perfect budget-friendly watch for any day of the week. In addition to being both high-quality and very affordable, it’s classic design works well with any wardrobe choice, casual or dressy.
Now that you’ve got a great watch you can further mix up your look by swapping out different watch straps. Add a leather or suede one for a polished look or try nylon and perlon for something more sporty. Buy a few and switch them up depending on your mood, it’s easy and fun.
Finding a good backpack isn’t easy, and finding an affordable one is even tougher. That’s why I love this one from Knomo so much, it’s versatile and stylish without being too bulky, something that’s really tough to find at such a great price point.
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 $200 for the various men in your life.
Essentials Box
My all-time favorite company for ties and pocket squares has this great Essentials Box that includes ties, pocket squares, socks as well as tie bars & collar stays for the man who likes to class it up or needs a little help in the accessories department.
For someone into cocktails, this is a great addition to their bar that they might not have. It’s easy to give glasses, stirrers, shakers or booze, but a clear ice cube maker kit is a cut above the standard items one would give.
I’ve gone over the best backpacks or rucksacks before, and my top choices are definitely pricey, but for an everyday, go-anywhere, do-anything bag, this one is my top choice. I love that it comes in different colors in case your recipient may prefer something other than black.
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.
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.
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.
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.
$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.
I’ve already talked pretty extensively about ties and pocket squares in my Men’s Essential Accessories series, so if you haven’t sen those articles/videos and don’t know the size of ties you should be wearing or the best ways to fold your pocket squares, check them out. The wool ties & pocket squares I’ll be discussing below are essential for the Fall and Winter seasons because they will compliment the items in your Fall/Winter Wardrobe nicely.
Material
For your ties and pocket squares during this season, you need to go all in with wool. There’s also technically cashmere, but there’s not a lot of them being made and I find them to be obscenely expensive when a wool tie looks just as good.
The reason you go all in on wool is because you want your accessories to compliment the fabric weights of the items you’ll be wearing during the various seasons, so if you were wearing silk or linen ties, which are for Spring and Summer, with your heavier wool suits or sport coats, it would look really off.
Colors
As I mentioned in the Series intro, this is the time of year to wear some nice, rich colors, like:
greens
shades of blues
burnt oranges
grays
burgundy
browns
Patterns
As far as patterns, it’s also the best time of year to wear plaids, paisleys and polka dots because they’re visually heavy and pair so well with your Fall and Winter wardrobe.
The one area that I see men really have an issue, though, is with matching these patterns and colors together with their outfits or other accessories.
A good rule of thumb is:
If your tie is a bolder pattern, like a paisley or plaid, then you want your pocket square to be more subtle or as close to a solid color as possible. It doesn’t have to be a solid, but when in doubt, go for a solid one. This ensures you don’t have too many patterns clashing. (See the video above and outfit images below for examples)
And the inverse is true for a patterned pocket square – go for a solid or very subtle patterned tie.
This helps balance these items out so you don’t look like a goofball.
The ties from Tom Ford, Alexander Olch, and Thom Sweeney are pricey, but you’re paying for a high quality, luxurious accessory that’s timeless. If you’re going to shell out this amount of money for a tie, then you want to make sure it’s easy to wear and it’ll never go out of style.
For fun patterned ties that are also easy on the wallet, I’m a huge fan of The Tie Bar (and no, they’re not paying me to say this). For great textured wool ties in solid colors, I love J.Crew. They also made a charcoal chalk stripe tie that is really easy to wear with your existing wardrobe.
Brunello Cucinelli makes probably the best – in terms of color, pattern, and quality – pocket squares out there, in my opinion. The Hugo Boss and Alexander Olch pocket square and rounds are all the perfect shade of grey so they’ll pop really nicely from your darker suits or sportcoats.
The striped J.Crew pocket square will go with pretty much every Fall suit/sportcoat you have. For some great patterened options at an incredible price point, I love the double sided ones by The Tie Bar.
If you’re relatively new to pocket squares, the worst thing you can do is go overboard with them. I see it all the time. It’s a very fine line between looking sharp and tacky. Classy and subtle wins out over loud and flamboyant every time. So please don’t complicate your pocket squares any more than necessary.
Before we get into the pocket squares you should own, let me answer some of the common questions I get asked about pocket squares.
Do I always need to wear one with all my suits and blazers?
No, but I’d suggest wearing one more often than not. To me, the more casual the outfit, the less necessary one becomes. But even then, the quickest way to add a little extra polish to an outfit is with a pocket square.
How Do I Match My Pocket Square to my outfit?
First off – if you’re matching your pocket square to your tie exactly – stop immediately.
Matching your pocket square to your outfit is pretty straight forward.
The safest thing you can do, which looks great 100% of the time, is to match your pocket square to your shirt. You will NEVER go wrong there – as long as you’re not wearing some obnoxious dress shirt color like red or orange. Even then, it wouldn’t look… horrible. So do that if you’re going tie-less or wearing a black tie.
Solid tie that isn’t black
Make sure your pocket square is a similar color (not exact) to the color of your tie. Or, if you’re using a white pocket square with colored tipping, make sure the tipping is a similar shade of the same color.
Patterned tie
Find a color in the tie and have your pocket square, either the tipping, pattern, or solid color of your pocket square have a similar color in it. It doesn’t need to match perfectly, but it should have a similar shade of the color as your tie. So if you’re wearing a blue tie, have a blue shade in your pocket square.
Plain tie
Match your pocket square to your dress shirt. It doesn’t need to be perfectly matching, just a similar shade of the same color. That will keep a nice contrast between the items you’re wearing.
Going Tie-less
Again, match your pocket square to your shirt color.
So if you’re wearing a blue suit and white dress shirt, then you can wear a white pocket square.
What Material Should My Pocket Squares Be?
This one is simple: cotton.
Cotton works in 100% of situations, no matter the outfit, color, etc. and goes perfectly with your essential silk ties. So don’t waste your time or complicate things further by even considering other materials.
I occasionally use wool or linen pockets squares with clients or on shoots, but they have very specific use cases and cotton pocket squares would still work in all of these situations, so stick with cotton and you’ll be just fine. For silk pocket squares, I think I can count on one hand how many times I’ve used them over the course of my career.
What Colors and Patterns Should My Pocket Square be?
I’ll always default to classic and timeless colors and patterns so stick with these and they’ll go with any suit or jacket you’ll own:
Plain white (if you have 1 color, this is the color)
White with gray or navy tipping
Navy or gray gingham patterns
Any other types of patterns or colors and you’re venturing into territory that’s outside the scope of this series and where things can go wrong very quickly if you don’t know what you’re doing – and trust me, most guys don’t know what they’re doing in this department, even the so-called “experts”.
I’ll do a whole other video or series about patterns and materials later on, but that’s next level stuff and is not appropriate for the Essential Accessories Series since these are the items that need to work with my Men’s Wardrobe Essentials and also need to work for every guy, regardless of his age or body type.
Honestly, it’s hard to go wrong with any pocket squares, as long as they’re cotton and you’ve stuck to plain white, white with colored tipping and navy or gray gingham patterns. So if you have a preferred place to get your pocket squares go ahead and use them.
I get hit up by a gazillion tie and pocket square companies all day long, but for all my pocket square needs – and they’re not paying me to say this – I use TheTieBar.com.
I’ve been a customer of theirs since they were a little company, who didn’t know who I was or what I did for a living and and they’ve continued to impress me each and every time I order from them. Suffice it to say, they’re amazing. And trust me, I use them A LOT.
The Tie Bar Solid White Cotton Pocket Square
The Tie Bar Solid Pocket Square with Navy Border
The Tie Bar Cotton Pocket Square with Dark Charcoal Border
The king of all pocket square inspiration photos is my friend Rainier over at TheDressedChest.com, my images below pale in comparison to his, so go check him out, as well.
Just like all the other essential accessory pieces, you want your ties to work perfectly with all the items in your essential wardrobe. If you own a suit or blazer, then you absolutely need ties! Unfortunately, I see a lot of guys also completely crapping the bed with their ties.
the wrong material or fabric weights for the outfit
A big mistake most men make, whether they’re just starting out or have a little better handle on their personal style, is thinking they need to go overboard and have their accessories be these big statement pieces. That’s when men get into trouble.
Some men think it’s “boring” to stick to the basics, but they’re basics because they work for everybody and look timeless and sharp. And with the right accessories to round out your outfit, you’ll look well-dressed throughout your entire life. If you never own another type of tie in your life, my suggestions will cover you for every situation you’ll ever need.
How to Match Ties To An Outfit
The most common question I get about ties is how do you match them to and outfit. And it’s pretty simple:
The safest thing you can do, which looks great 100% of the time, is to have a similar color in your tie (not exact, just a similar shade) to any other color you’re wearing in your outfit – outside of your dress shirt.
So if you’re wearing a gray suit, white dress shirt and black dress shoes, wear a tie that has black or charcoal/gray in it. If you’re wearing a navy suit with brown dress shoes and charcoal socks, wear a blue or charcoal tie. If you’re wearing a gray blazer with dark wash jeans and brown boots, wear a tie that has some blue or charcoal in it. Brown leather jacket and boots, wear a tie with some brown in it.
That’s it.
Anything outside of that is next level stuff and can go wrong quickly if you’re not sure what you’re doing. You can go your entire life only following this rule and you’ll never go wrong – I promise.
What materials should your ties be?
You really only need ties in two materials to cover you for the whole year.
Silk Ties Silk ties work year-round with every kind of outfit where a tie can be worn – dress, business and casual.
Knitted/Woven Ties For the Spring and Summer months only – Check out Summer Essentials Ebook for details about those specific ties, but since they’re not for year-round wear, I won’t cover them in this article.
Any other types of materials, like pure wool or linen, have pretty small use cases and definitely won’t be as versatile as the above options and you should wait to get them until you’re much further on your style journey.
What color ties should you own?
Like all the items I recommend in the essential wardrobe series, you want to stick to black, charcoal, and navy, with one exception – which you can throw in there, if you like, and that’s silver or light gray.
These colors will go with 99% of the outfits you’ll wear. Just like with tie materials, any other colors will have specific use cases and are outside the scope of this series.
Once you’ve gotten those basic colors, then and only then can you start expanding to lighter shades or darker or brighter colors like burgundy, brown and other pastel or jewel tones. Again, that’s once you get more comfortable and really understand how to add them to an outfit.
But if choosing tie colors is still tough for you, then those default colors go with pretty much everything and you’ll never have to worry about not looking sharp and put together.
What patterns of ties should I own?
First, stick with plain, solid colored ties in the colors I discussed in the previous section. Then, you can move onto some striped ties with no more than 3 colors in them (ensuring at least the major color in the tie is one the colors I discussed above) and you can also throw in some smaller polka dotted ties in there, too. Also in the same colors I discussed previously.
What Size Tie Shoud You Own?
Follow these rules for your tie widths based on your height and body type so your proportions will always be balanced. Trust me, I deal with clients of all shapes and sizes all day long and these tie widths will work for you.
Tie lengths really don’t come into play because most places you’ll go don’t make tall or short versions anyways and they’re not entirely necessary unless you’re ridiculously tall (over 6’5″) or short (under 4’10”).
To take your tie width measurements, just use the widest part of the tie near the bottom.
Under 5ft 8in and very thin
You need to get a 2″ width tie. If you’re not sure if you’re very thin, then you probably have an average build. Under no circumstance should you ever wear this width of tie unless you’re very thin and under 5’8” because it will look silly on you. I’d say that at least half the men I see wearing skinny ties shouldn’t be. Don’t fall into that group!
Under 5ft 8in & average/broad Build
Wear a tie that is 2.5″ wide.
5’8” to 6’3″ tall
thin to average Build
Wear a 2.5″ wide tie.
Large/Broad Build
You need a 3″ wide tie.
6’4″ tall and above (no matter your build)
You need a 3″ wide tie no matter what. This will help balance your proportions.
The Best Men’s Ties
I’ve been a customer and user of TheTieBar.com for years now, and they continually prove to me that they are, by far, the best place to get quality, affordable ties. I have never taken a dime from them to promote their products because they deserve all the praise and business in the world. Unless a designer has specifically made a tie for a client, I use them every time.
