How To Look Cool When It's Freezing Cold – Air Tailor
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How To Look Cool When It's Freezing Cold

Old Man Winter was a bit of a hermit towards the end of 2015. Only recently has it been FLIPPIN' CHILLY (here on the East Coast, that is). Whatever winter decides to do moving forward, you should have your winter clothes ready for when the temperature drops below freezing and a few more snowflakes hit the ground.

Now is the time to get all your winter stuff out of the closet and on to your body. You can wear your nice looking pea coat out for a stylish stroll. For really bad weather, you can zip into a big down jacket. Of course, no winter ensemble is complete without the coordinated accessories of a hat, scarf and gloves. You can even break out the really warm wool socks.

But having the right outerwear and accessories for winter seems like a bit of a no brainer, doesn’t it? Like with people, there’s more to winter wear than what is on the outside—your shirts and pants, for instance.


The best place to start thinking about being warm for the winter is by considering what fabrics to wear. During the winter, you want to wear thicker and more tightly woven fabrics which let less air in.  A flannel shirt works best for a casual look. An oxford shirt is a versatile item which can be dressed up or down for a variety of occasions.

As for pants fabric, it’s a great time to wear corduroy and wool. If you’re going for the full suit, both flannel and wool, especially tweed, are great choices.

A nice mix of warm fabrics. The burgundy knit tie acts as a pop of color.
Photo by Sven Raphael Schneider for The Gentlemen’s Gazette.

Even ties can help you keep warm. Heavy fabrics, like wool or even cashmere, are good choices to help you be just a little bit warmer. For less formal situations, you can wear a knit tie and add a bit of texture to your overall look. However, your tie options are not totally limited as the everyday silk tie can be worn all year round.

If you’re struggling to come up with winter shirt-and-tie combination ideas, check out this gallery of 20 options by GQ.

The next thing to think about is layering. It seems like an easy idea: your clothes help keep you warm, so more clothes should make your warmer. While that’s correct, you shouldn’t just pile on clothes with no rhyme or reason. As much as you may like that certain chunky sweater, it won’t work under a light blazer. Thankfully, the folks over at Primer spoke to Barron Cuadro, founding editor of Effortless Gent, and came up with this handy visual guide to winter layering:

Visual by Andrew Snavely for Primer

So if you’ve missed your favorite merino wool sweater or cashmere cardigan, winter is the best time to incorporate them into your ensembles. There’s even down winter vests that are thin enough to wear under your suit jacket. Oscar Isaac of Star Wars fame, below, pulls off the look excellently.

We make no promises that you’ll look as good as Oscar Issac, but perhaps you might look just as stylish this winter.
Photo by Nathaniel Goldberg for GQ


Of course, fit is always important. It might seem intuitive to go a little looser for the winter—I mean, how else are you going to fit your undershirt and long johns under your clothes? While you might want to leave some room, you shouldn’t go too bulky or loose. You can keep warm and still have a sharp, tailored fit. Besides, you don’t want things loose enough that it lets the cold air in.

Air Tailor makes the tailoring process easy and affordable. All you need to do to start the process, after signing up with us, is send a text message. Someone from the Air Tailor team will guide you through the initial steps of preparing your garment for alteration. If you have any additional needs, you can just text them to us.


Now that we’ve gotten you through the things that are sure to keep you warm, we can talk about what will make you look cool—and that’s colors.

Winter is a time where people tend to wear bolder and darker colors, especially compared to the soft and bright colors of the spring and summer. Of course, you have your somewhat neutral colors: white, black, shades of greys and darker shades of brown. You also have the colors on the cooler end of the spectrum: greens, blues and purples and all the colors in between.

However, you don’t have to banish red, yellow or orange from your closet until the middle of March. Rich, bold reds work as a great contrast to subdued greys and blues. Darker shades of yellow and orange, like mustard and burnt sienna can work, but it may take some experimenting. These warmer colors and lighter shades of colors can be incorporated as pops of color, like a lavender shirt collar with a black sweater, or when used as a statement piece, like a deep red pair of pants in an outfit full of black and greys.

A nice gray flannel suit paired with a coral sweater that adds a nice pop of color.
Photo by Andrew Snavely for Primer

When the forecast outside tells you it’ll be freezing, hopefully this guide to the basics of warm winter wear will have you prepared and looking debonair.


If you are looking for more advice about what to wear during the winter, check out these great guides:

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