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.
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.
In this video, I talk about the 21 things men should never wear! These are the things that’ll curl your toenails, and offend even your grandmother. Just don.do.it.
Q: I’ve lost a significant amount of weight and now all of my clothes are clownishly large on me. Can a tailor make my clothes fit again or should I just buy all new ones?
A: See the video above for the answer and my men’s clothing fit guide for how your clothes should fit.
Q: I watched your T-Shirt video and if I have a nice looking tee with a pretty minimalist design, does that hinder a look the same way a straight up graphic tee would?
A: Short answer – sort of. See the video for the longer answer.
Q: As a shorter man (5’6″), I find it difficult to find stuff that fits me and looks good. I was hoping you can provide some general style tips for shorter men.
Q: I recently picked up a Briefcase in a navy/ tan leather color way, would I match my wallet/watch/belt/etc. To the bag? What would you do in my situation?
A: Don’t think about it too much. Andrew is less of a stickler here, but I am more of a stickler. See video for details.
A Polo Shirt is a great, versatile item that I put all my clients in at some point of us working together. They’re timeless and a cornerstone of any good spring or summer outfit. I often recommend wearing them in place of t-shirts, as they give a casual outfit a bit of polish – which is never a bad thing. No matter your age or body type, every guy needs a few polo shirts in his wardrobe.
A good polo shirt will:
Fit like a glove.
Enhance the good parts of your physique and hide the imperfections.
Make you look more polished and put together.
Layer incredibly well.
Only have short sleeves – long sleeved polos have no place in your wardrobe.
Fabric
Fabric choice is the biggest thing to consider when choosing a polo shirt and heavily dependent on your body type. The fabric you choose will determine how good (or bad) you look in a polo shirt.
Piqué Cotton
Piqué cotton polo shirts are made with cotton yarn and have thin ribbing visible in the garment. The texture is soft, and if you look closely you can see the tightly raised cords that give a waffle-like appearance.
Piqué polos are best for heavier-set men with wider physiques because the textured fabric hugs the body without conforming to the less flattering areas of the chest and stomach. When I’m working with a client who’s worried about his belly being accentuated, I always go with pique cotton. Think of the fabric as airbrushing your torso and hiding the problem areas.
Check out how much more flattering thepiqué cotton polo is on the same guy compared to a cotton/silk blend polo. I bet his hands are covering his belly button divot in the cotton polo shirt picture, too. It’s an old photographer’s trick. Notice his chest area looks a little more smoothed out? Please don’t think I’m recommending this polo, it’s pretty bad (that’s a horrible sleeve length) but it highlights the “airbrushing” effect that piqué cotton has very nicely.
Cotton & Cotton Blended Polos
If you’re in decent shape, skip the piqué polos and grab a few cotton/cotton-silk blended polo shirts. The material looks better on your body type and is softer and more comfortable than pique cotton. These polos have a sleek, modern look that are great on their own or underneath a jacket. Beware, it’ll shine a spotlight on your body’s imperfections if you’re not in good shape!
Colors, Patterns, Piping, Etc.
Avoid any patterns or collar/sleeve piping and stick with the basic (and best) colors to begin. Grab a few white, black, navy, and charcoal/gray colored polos. They’ll give you the most versatility with the rest of your Essential Wardrobe and will work with any skin tone and body type.
If you’ve got the basic colors already, definitely get some brighter colors that compliment your skin tone and/or throw some stripes in there, too. I would universally avoid plaids or any other wackier patterns, it’s just too much and looks tacky.
To Tuck or Not To Tuck
If you’re wearing a polo shirt without a jacket, then don’t tuck your shirt into your pants. I know golfers do this, but you’re not on a golf course and it looks horrible tucked in.
If you’re wearing a jacket, then loosely tuck in the front part of the shirt by your belt buckle like in my 3 ways to wear images below. The shirt should still cover the top half of your belt buckle – you don’t want to completely see the buckle. I love doing this on my clients because it breaks up the outfit when you see a little of the belt buckle and gives it a little polish without overdoing it.
Leggo my Logo
Please don’t get a shirt with a huge logo all over it. Just. Don’t. Logos that are small and the same color of the rest of the shirt are passable, but if you have the option, go logo-less.
For a pique polo, I recommend the Sunspel Riviera Polo Shirt. This shirt was made for Daniel Craig as James Bond in Casino Royale. A black or navy polo pairs well with either dark wash jeans or grey wool trousers. For a silk/cotton blend polo shirt, I love John Varvatos and Burberry. The shirt’s impressive construction and fit is well worth the price.
I’m a big fan of H&M’s cotton polo shirts. Actually, I would probably get those over the designer options a majority of the time. They won’t last forever, but they’re cheap enough to replace every season or two. They have a clean design with a great fit and a price that you can’t beat. The model in the first picture below is wearing the H&M Polo.
The jacket and chinos are actually from Dsquared2, but they’re for an upcoming season and not available in stores at the time of writing. So I added the best substitutes below.
Philipp Plein Coat So Cool
Tom Ford Short Sleeve Pique Polo Shirt
Brooks Brothers Slim Fit Darak Khaki Garment-Dyed Chinos
Wool pants and trousers are an essential item because they’re the middle ground between jeans/chinos and a full suit. In situations when jeans or chinos might be a bit too informal and a suit is overkill, the wool pant/trouser fits this spot perfectly. They’re also amazing because they look damn good on every body type.
I want to clear the air about something first, because it’s important for you to know this:
The category of wool trousers is quite broad and basically includes any pants that are made of wool. This means trousers made of a more lightweight fabric, like suit pants, and the traditional, heavier-weight wool trouser are all considered “wool trousers.” If you want to get technical, I’m specifically meaning a wool fabric weight of anywhere from about 10-12oz and up.
When I say wool trousers from this point forward, I only mean the thick/heavier-weight wool trousers because the lightweight fabrics, like suit pants, look flimsy and unpolished when worn with items outside of a suit jacket. The thicker weight of the wool trousers I recommend below will not wrinkle as easily, lay cleaner on the legs and look great with everything from a sweater or overcoat/peacoat and semi-spread collared shirt (oxford button down dress shirt, too) to a leather jacket and t-shirt. Basically anything in your essential wardrobe will look great with the recommended wool trousers.
Some of my older readers often ask about “slacks” or “suit trousers” and my answer is always the same: don’t bother. You should never be wearing slacks or suit pants or similar without a full suit. Its flimsy looking, tacky and the mark of a guy who doesn’t know what he’s doing.
To Pleat or Not To Pleat
I don’t care how old or young you are or what your body type is – whether you’re thin or a larger guy, you should NEVER, EVER have pleated wool pants. Honestly, I f*#@%ing hate them because they’re so unnecessary and are unflattering on every guy. I’ll be the first to dance on their grave if they ever completely go away. I’ve never seen a guy look good while wearing them – ever.
What Colors Should You Get?
I’d recommend having at least two pairs of wool pants in your wardrobe. My first choice would be gray, then dark blue, and then brown, if blue or gray wasn’t available. Black is OK, but I’d consider that my last option, if I were you. It’s just too heavy of a fabric to wear black in, as it’ll look more imposing.
Crewnecks are okay, but they’re a more casual item. So for this reason, a V-Neck sweater is essential because it’s the classy mofo of the sweater world. V-necks add a touch of dressy formality that you just won’t get with a crewneck.
I love crewnecks, don’t get me wrong, but most guys don’t know how to wear them so then it starts looking really sloppy. I know some guys like the crew neck and tie or suit look, but I would choose a v-neck or cardigan sweater over a crewneck in this case almost every time.
Let your partner borrow them to snuggle with or wear
Throw them out if they get worn or thin around the elbows or the collar gets stretched out
Don’t
Wear them with a dress shirt and have the collar resting on top of the “v”
Wear them with shorts
Wear them over Polo Shirts (ever)
Wear them over T-Shirts (ever)
Wear them without any shirt underneath – gross!
Wear them if they have any holes, pilling or they’re worn thin around the elbows
Fabrics
I prefer the V-Neck Sweaters I work with to be made of wool, – either regular or merino wool. Cashmere is also a great fabric, but it’s definitely on the pricier side. If you run a little warmer, then go for a wool/silk or cotton-blended sweater – Pima cotton is also great, but it stretches out very easily.
Colors
You need at least 1 black V-Neck Sweater in your closet. If you’ve got a black one already, grab a navy and/or charcoal gray version. These colors will go with everything else in your Essential Wardrobe. If you want a 3rd option, then a darker brown will also go pretty well with your wardrobe, too.
I love each one of these v-neck sweaters, especially the H&M and Life After Denim sweaters. Even though they’re budget-friendly, the quality, fabric weight, and overall fit is really good.
J.Crew Black Wool V-Neck Sweater
Life After Denim Charcoal Tournament V-Neck Sweater
