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:

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:

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.

Wool Ties & Pocket Squares

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.

Best ways to wear Wool Ties and Pocket Squares

TopMan Selected Homme Brown Wool Rich Suit Jacket
The Tie Bar Chambray Shirt
The Tie Bar Wentworth Plaid
The Tie Bar Kingsley Attune Pocket Square
The Tie Bar Metallic Navy Tie Bar
Diesel Buster 0607A Jeans
Allen Edmonds Poplar Dress Belt
Johnston & Murphy Nolen Double Monkstrap Shoes
John Varvatos Prince Sunglasses
H&M Wool-Blend Blazer Slim Fit
Burberry Slim Fit Cotton Poplin Shirt
The Tie Bar Score Check Tie
The Tie Bar Olive Green Tie Bar
The Tie Bar Southeast Plaid Pocket Square
Diesel Buster 0607A Jeans
Allen Edmonds Poplar Dress Belt
Allen Edmonds Strand Cap-Toe Oxfords with Dainite Rubber Sole
IWC Portugieser Automatic Dress Watch
Tom Ford Snowdon Sunglasses

The Best Wool Ties

J. Crew American Wool Tie in Chalk Stripe

J. Crew English Wool Silk Oxford Olive Tie

J. Crew English Wool Silk Oxford Burgundy

Notes About My Recommendations

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.

$250 – Tom Ford Dot Wool Tie
$180 – Drake’s 8cm Houndstooth Wool and Silk-Blend Tie
$160 – Alexander Olch ‘The Spot’ Knit Necktie
$60 – J. Crew American Wool Tie in Charcoal
$20 – The Tie Bar Webster Medallions Tie
$20 – The Tie Bar Score Check Tie
$20 – The Tie Bar Woolf Houndstooth Tie
$20 – The Tie Bar Wentworth Plaid Tie

The Best Pocket Squares

Brunello Cucinelli Circled Dot Wool and Silk Boucle Pocket Square

Alexander Olch 'The Birdseye' Wool Pocket Round

Alexander Olch 'The Windowpane' Wool Pocket Round

J. Crew English Wool Silk Pocket Square in Stripe

The Tie Bar Kingsley Attune Pocket Square

The Tie Bar Wentworth Houndstooth Pocket Square

The Tie Bar Southeast Plaid Pocket Square

Notes About My Recommendations

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.

$95 – Armani Collezioni Chevron Patter Pocket Square
$95 – Marwood Slub Pocket Square
$60 – Boss Wool Patterned Pocket Square
$60 – Alexander Olch ‘The Birdseye’ Wool Pocket Round
$60 – Alexander Olch ‘The Windowpane’ Wool Pocket Round
$30 – J. Crew English Wool-Silk Pocket Square in Stripe
$10 – The Tie Bar Kingsley Attune Pocket Square
$10 – The Tie Bar Quest Tooth Pocket Square
$10 – The Tie Bar Wentworth Houndstooth Pocket Square
$10 – The Tie Bar Southeast Plaid Pocket Square

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 photos… shudder.

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 Navy Border

The Tie Bar Cotton Pocket Square with Dark Charcoal Border

The Tie Bar Navy Cotton Table Plaid Pocket Square

The Tie Bar Metric Plaid Charcoal Pocket Square

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.

Get This Look: Layering With Shades of Blue

When it comes to color, blue looks great on every guy. I love creating outfits for my clients that are composed of shades of blue (like I mention in this video). In sticking with the same color family, you can mix and match patterns creating an even sharper look.

Take note of the above outfit: A navy chalk striped wool suit worn with a light blue cotton dress shirt, navy wool tie, blue tipped cotton pocket square, and blue and white dot scarf. The suit, alone, can look very boring and conservative. However, mixing patterns within the blue color family, creates a sharp, eye-catching outfit.