How To Dress Casually This Winter

Don’t get me wrong. In the winter, I love a good flannel suit or tweed sport coat.  Recently, though–for obvious reasons–I’ve found myself experimenting with the casual side of the spectrum.

Perhaps especially in the doldrums of winter, it’s easy to fall into the trap of throwing on sweatpants and whatever hoodie is laying around. It’s comfortable and doesn’t require much thought.

But, I think there’s value in styling casual looks in an elevated way.  I’ve put together a whole week’s worth of winter casual outfits for both indoors and outside to do just that.


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Lately, I’ve been really into 1970s Robert Redford style. Think “Three Days of the Condor”–peacoat, layered sweater, hiking boots– without the oversized aviator eyeglasses. This is 100-percent influenced by that movie. The navy peacoat is a winter staple, but the braided leather gloves make it more visually interesting.

Layers come in with an ice-blue button up and tan sweater. Light wash denim to complement the tan boots. Redford’s boots might have been a little different than mine…but, whatever.



There’s nothing wrong with a hoodie and sweatpants. I’m sure people crank out great work that way. For me, though, even if I’m just sitting around or working at home, adding elevated touches to a basic outfit gets me in a productive mindset.

So, taking a ‘Canadian tuxedo’ built around a Western shirt and raw denim and layering with a cashmere cardigan and some of my favorite Belgian shoes helps to level up an otherwise casual outfit.



A mid-week sporty and casual winter outfit with faded jeans and a super comfortable cable knit sweater. The sweater is so thick and warm you really don’t need more than this quilted vest as outerwear.

Adding some shearling gloves from Hilts-Willard and a soft wool knit cap from Drake’s offers some interesting contrast with the blues and blues in the rest of the outfit. Finish with white sneakers and you’ve got a hump-day look that’s very easy to style.



Playing with a little color here. The burgundy turtleneck makes for an interesting contrast with the wool overshirt. The stripe isn’t an exact match; but that’s kind of better. It gets a little chilly down in the studio, and throwing one of these on offers a much more laid back, at-home kind of feel. As we’re going bolder up top, a neutral base in black jeans and black suede loafers balances everything out.



The shacket returns- this time with some dark denim. Since we’re taking this look outside, I’m throwing on this jacket, a classic plaid scarf, and Wednesday’s hat and gloves.

Something I’ve also been doing recently is flipping up the both the shacket and jacket collars. It creates this cool layering effect and gives even a winter casual outfit like this a stylish twist. And, since we’ll be walking the dog, the L.L.Bean gum shoes are a necessity.



Saturday’s fare is light wash jeans and a brushed cotton button-up shirt. A merino wool quarter zip is an excellent way to layer a simple look like this. And, shoes with an interesting pattern (like the blackwatch plaid) show you put some effort in, even if you’re just kicking around the house.



Incorporating black jeans and Belgians again, but this time with a buffalo plaid shirt from Uniqlo. It’s interesting mix of both high/low and elegant/casual styles, but I think it totally works here. I’ve had this chunky shawl collar sweater for years, and it’s another great piece for layering around the house.

Even as we’re spending a little more time at home these days, a little effort into goes a long way for your style and your mindset. Putting together outfits like this can remind you there’s value in simplicity and knowing what works. Or, it can show you how to style old pieces in new ways.  Sometimes, that’s a good thing.

What are some of your go-to winter casual outfits?

Thanks for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style


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