My Fall to Winter Wardrobe

The temperatures are hovering nearer and nearer to that freezing mark and there is no end in sight... what do we wear to stay chic yet cozy this winter?

I suffer from Seasonal Affective Disorder and it feels like this year it has kicked in a lot sooner than usual. The only glimmer of light at the end of my SAD tunnel is the opportunity to reorganize my wardrobe for the season ahead. I like to keep out-of-season clothing in storage boxes out of sight, so that when a new season is on the horizon I can take everything out and it almost feels like a whole new wardrobe. It’s nice getting reacquainted with what you already own.

Undershirts & Cozy Socks

Let’s start off with the most basic of basics: what goes underneath. I like the plain tanks from H&M year-round to keep my back warm but they come especially handy this time of year. They come in a black & white 2-pack for $9.99, they fit close to the body and wash well. Under more pretentious fabrics like silks or light coloured cashmere, I like to wear the Numi sweatproof undershirts because of their extra armpit sweat protection. The nude colour is undetectable under white silks and it’s a great way to keep your more prized items of clothing safe from sweat stains.

For the ultimate warmth - Uniqlo Heattech fabric is king. Their turtlenecks, long sleeves and bodysuits make for excellent cold weather layering pieces without adding bulk to your outfit, and they also make socks in the same insulating fabric. Thermal socks are a great way to keep your ankles warm while getting some extra mileage out of the shoes you liked to wear in early fall.

The Cashmere Layer

A neutral cashmere crewneck sweater is like the white tee of the autumn-winter wardrobe world. I would opt for one in black, grey or oatmeal to have all the bases covered. It’s a wardrobe staple that is easy to wear, whether dressed down with jeans and hiking boots or dressed up with a pencil skirt and a blazer. I prefer a more slim-fitting option so that it is easier to wear underneath blazers and coats. Everlane’s $100 cashmere crew is my go-to but Winners, Marshall’s, Uniqlo and H&M also have great options that don’t break the bank.

Chunky Knits

The bold, cozy closet staple that I look forward to the most - I love a chunky sweater this time of year. H&M is my affordable stand-by and Aritzia always has stunning cashmere options that catch my eye. I like to add one new statement knit to my wardrobe each year, and this year I opted for the camel-hued wool Weekend Max Mara number pictured below. This H&M option is similar for $29.99. Chunky knits work well just with an undershirt and with a scarf if it’s not too chilly, with leather leggings and heeled ankle boots for an evening twist or with snow boots and a parka when the temperatures sink.

Oversized Scarves and Blazers

The more fabric to snuggle with, the better! Oversized scarves are great for bundling up on a windy day or for an extra blanket during travel. My go-to is always a grey wool one because the colour is so versatile and works with everything in my wardrobe.

When it comes to blazers, larger boxy shapes reign supreme this season. I love the vintage blazer selection at The Oversize Store or buying a classic like Madewell’s Caldwell Double Breasted Blazer $158.00 or the GAP Modern Plaid Blazer $80.00 in a size up for the right fit. Perfect for that masculine touch and for layering over chunky knits. Last weekend I managed to stay cozy without a winter coat, just by layering an undershirt, chunky H&M knit, oversized blazer and wool scarf to keep warm in the near-zero temperatures.

The Wool Duster

I managed to fulfill my long wool coat dreams earlier this year when I found a preloved Gucci coat deeply discounted at a consignment shop online. Second-hand shopping has been my favorite way to shop lately. It always feels special when you come across that cool piece you’ve been hunting for, plus it’s a way more sustainable way to shop. A few years ago I found a vintage wool cape from the 1960’s that was in such good shape it could be mistaken for brand new and I still feel special every time I wear it.

The Black Leather Jacket

Now depending on where you live, a leather jacket might not be that practical from fall to winter. I’m going to keep mine out for the time being because there are some +8 degree weather days on the horizon and I love the way an all-black outfit looks with a leather jacket. Black skinny jeans, black ankle boots, a black cashmere sweater and a leather jacket? *chef’s kiss*

Chunky Hiking Boots

Although they’re a quintessential wardrobe staple, it feels like hiking boots, especially super chunky ones, are having a huge moment this season. While I’m not going to invest in a pair of the super chunky lug soles I’ve seen all over Instagram, I’m more than happy to try and work with what I already have in my wardrobe. The fun part of this style of shoe being so ubiquitous now is that I’ve gotten tons of inspiration on additional ways to style my 2-year old pair of FEIT wool-lined hiking boots. For the last couple of years I’ve only worn them with jeans but this fall/winter I’m inspired to pair them with more traditionally feminine pieces like silk skirts and midi dresses to toughen up the look.

Boots featured, from top to bottom:

FEIT Wool Hiker $850.00
MANGO Lace-Up Leather Boots $119.99
& OTHER STORIES Lace-Up Leather Boots $179.00