Winter Accessories Every Man Should Own | Best Men’s Winter Accessories

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!

Hat 1

Hat 2

Budget-Friendly

 

A Patterned Scarf

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.

Picks:

Scarf 1

Scarf 2

Budget-Friendly

 

Gloves

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).

Gloves 1

Gloves 2

Budget-Friendly

 

Slim Dressy Watch

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.

Picks (from the video):

Watch 1

Watch 2

 

Merino Wool Socks

Merino wool has incredible technical properties (warm, lightweight and dries quickly) and there are great options out there that are lightweight, warm, and stylish. 

Our Favorite Merino Wool Socks

Another Pick

 

Thermals

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.

Thermals Pic

 

Extra-moisturizing skincare products

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.

Picks:

Moisturizer 1 – Get 30% Off With Code Ashley30

Moisturizer 2

Moisturizer 3

Moisturizer 4

 

Leather Lace-Up Boots With A Rubber Sole

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.

Picks:

Dress Boots 1

Dress Boots 2

Casual Boots 1

Casual Boots 2

 

Dorian’s Outfit Details

Jeans

Boots (similar)

Glasses

Peacoat

Sweater

Gloves (similar)

Scarf (similar)

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

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.

Pocket Squares

Pocket squares are an essential accessory because when I talk about the smaller details that set the average guy apart from the well-dressed gentleman, this is exactly the type of accessory I’m referring to. It’s an easily forgotten item that adds a little extra polish to an outfit and really sets you apart from the average guy.

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.

When to wear pocket squares

Anytime you’re wearing a jacket, either with a full suit or a blazer or sport coat. You can also wear them with unlined/unstructured blazers like I discussed in my Summer Essentials ebook. But, never, and I mean never, should you wear a pocket square with an overcoat or top coat.

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.

It’s a rookie mistake I see a lot of guys making and it looks bad 100% of the time. I just think of all those silk tie and pocket square sets in prom photosshudder.

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.

How to fold a pocket square

Check out my article and video about the 3 best ways to fold a pocket square.

Best Pocket Squares

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 Midnight Navy Border
The Tie Bar Solid Pocket Square with Dark Charcoal Border
The Tie Bar Novel Gingham Navy Pocket Square
The Tie Bar Metric Plaid Charcoal Pocket Square

Pocket Squares Outfit Inspiration

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.

How To Fold A Pocket Square

In the below video, I show you the 3 best ways to fold and wear your pocket square, depending on the material, whether it’s cotton, silk, linen or wool.