in: Featured, Outfit Guide, Style

• Last updated: June 10, 2021

6 Holiday Style Tips For Men

Men enjoying drinking party illustration.

The holiday season has begun, and for the next month many of us have a full schedule. From work-related parties to the traditional get together with friends and family, you’ll need to dress appropriately as you mingle with the boss and trade stories with uncle Bob. With many of these events scheduled for the same day, you’re going to have to balance comfort, style, and versatility. And believe it or not, this is easier than you might think.

1. Layer – learn to overlap cotton and wool clothing appropriately
Whatever you are going to be doing, you want to be comfortable doing it. A big part of that is wearing clothing that doesn’t cause you to overheat, allows your skin to breathe, and protects you from the elements. Both cotton and wool are time tested fabrics that when layered appropriately can help you make it through the holidays without freezing or breaking a sweat.

Cotton, the world most popular fabric, is what you want to wear close your body.Cotton fibers are a cellulose based fiber whose natural properties allow it to pass both heat and moisture, thus making this clothing breathable and light feeling.Cotton briefs and undershirts are inexpensive and provide you exactly what you need; 100% cotton dress shirts are usually priced a bit higher than blends, but if you expect to sweat there is no substitute for its wicking properties.A bonus is that cotton is very durable and can be safely washed at home with regular detergent, although acidic stains (such as those caused by wine) should be treated immediately.

Wool (and other protein based fibers such as cashmere), on the other hand, does an excellent job of retaining heat; thus these natural fibers are an excellent choice for a jacket, sweater, or overcoat.Wool also has the unique property of being able to absorb moisture while not feeling wet; thus the melting snow on your shoulders will disappear quickly and not spread. Little things like wearing wool socks and ensuring your knit hat is made of wool or cashmere (vs. cotton) will help you stay much warmer without adding any bulk. However, treat wool like the premium fiber it is.Water weakens wool’s strength, and it can be misshaped if hung up on a hanger when wet (instead lay out on a flat surface).Finally, never expose wool to extreme heat such as an iron; if you need to work out wrinkles, use a steamer so you don’t damage the fibers.

An ideal cold weather holiday outfit would combine 100% cotton underwear and dress shirt with a pair of wool trousers coupled with a wool sweater and jacket protected by a wool overcoat.If you find yourself sweating, you can rest assured knowing the cotton will wick the moisture from your skin and your wool jacket will absorb it with no noticeable effects.And by layering, you can always adjust your own personal thermostat by un-layering (try to keep your jacket on….unless the party gets lively!).

2. Invest in an Overcoat
You iron your shirt, polish your shoes, and adjust your tie – only to ruin the entire presentation by tossing on a bright red ski coat or old leather motorcycle jacket. Does this sound familiar? When it comes to a professional looking coat, many of us look at this as a luxury. But in the winter, your outerwear is the first and last thing many people will see you wearing. If the event is outside, it’s the only thing they’ll see. Far from being a luxury, a good overcoat is must for any man living in a region that experiences cold weather.

Unlike shirts or even suits, most men need only one overcoat. As such, it’s worth spending the resources to ensure it looks great on you. Start with fit; a $200 overcoat that fits a man perfectly always looks better than a $2000 overcoat that’s two sizes too big. First ensure the shoulders fit well and have a style that compliments your build – this cannot be altered. Next, look at the sleeve length, and have them adjusted to cover your jacket and shirt cuffs but not your hands. Finally, have a skilled tailor tighten the jacket around the torso and have its length adjusted to your tastes. As for fabric, as long as it is made from wool you are good to go. More expensive overcoats utilize a wool & cashmere blend – the added benefit here is drape and softness (not heat retention).

An overcoat does not stand alone – ensure you supplement it with a wool or cashmere scarf & knit hat and insulated leather gloves.For reasons mentioned above, it’s worth spending a little more for quality accessories made from the proper materials that will do their intended job.

3. Wear a Jacket
Many holiday parties will not require a suit; however this doesn’t give us the freedom to show up in sweats. This holiday season consider wearing a sports jacket or blazer – match it with a pair of jeans and button down shirt for a casual yet professional appearance at your company’s afternoon Christmas party and then transition seamlessly to the evening’s get-together with friends downtown. There are a number of advantages sports jackets and blazers have over dress shirts alone:

  1. Jackets build up your shoulders; this makes you look taller, and broad shoulders create a more masculine appearance.
  2. A jacket and dress shirt fits within the business casual dress code – this means you can skip the tie.
  3. For those with larger midsections, a jacket helps hide extra weight.
  4. Interior pockets are a great place to keep phones, money, business cards, and beats stuffing your trouser pockets.
  5. When your date or significant other says she’s cold, you have an instant solution.
  6. It just looks cooler.

4. Avoid the Seasonal Tie & Socks
They appear every holiday season, and like good soldiers we accept them with a smile and wear them so our loved ones can see that we really do appreciate their thoughtfulness. Clip-on Christmas ties with Santa Claus and the bright red socks with Frosty the Snow Man: really, why do we do this to ourselves?

Here, more than anywhere, an ounce of prevention is worth a pound of cure. The best way to stop this from happening is to subtly suggest an alternative gift that is easy to find, light on the wallet, and supports a great cause. 

5. Opt for Dark Trousers or Jeans
Snow turns to muddy slush, and you can bet you’re going to get some splashed on you. Leave the khaki’s at home and wear a pair of dark trousers or jeans that can take a piece of dropped cake or spilled glass of eggnog without you having to change outfits. This tip also works for dates and interviews; as men, the one time you forget to “shake” properly is when you are going to be stuck confronting your date with an embarrassing wet spot near your crotch.

6. Always carry a Handkerchief
A gentleman should always be ready to help a lady, child, or fellow man in need. Carrying a simple white cotton handkerchief in your back pocket is a habit that’s inexpensive, easy to pick-up, and allows you to come to the rescue in a potentially embarrassing moment. Oh, and the proper response when they thank you is to say “You’re welcome, and please keep it”.

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