Top 5 Fall/Winter Trends To Know & Wear

A blonde woman wearing a blue vintage sweater, crossbody bag, oversized grey coat, and black combat boots, in front of a blue shipping container

Let’s talk Fall/Winter style trends.

My appreciation for minimalist and practical styles full of basics, both colour- and necessity-based, is quite alive and well. My personal style, on the other hand, has been shifting towards a masculine-inspired wardrobe, with an emphasis on semi-casual and feminine edge.

Without overusing all of my descriptive adjectives, I leave you with five of my favourite simple, easy, and affordable trends this Fall/Winter season. Hope you leave with opinions, ideas, and inspiration to create your own list of must-haves.


Midi Skirts

A woman in wearing a black midi skirt with a grey sweater, checkered blazer, black boots, and black purse.
Sweater: Aritzia, Skirt: Mango, Booties: Dolce Vita, Plaid Blazer: Zara, Crossbody: Mackage

Wether we are talking knits, pleats, leather, or corduroy, a midi skirt is to be considered a Fall/Winter trend to wear this season.

Opting for darker tones (i.e. colours of my soul) is preferred due to the factors of practicality, versatility, and inter-season wearability. I find both the shape, material, and colour to be slimming, as to even out the “bulkiness” of chunky knits and potential multiple top layers. Similarly, when paired with heeled booties, the heel and the high waist provide that effortlessly tall and long-legged effect.

a blonde woman posing in front of a CN Tower, wearing a black midi skirt, a thick grey sweater, a plaid blazer, sock booties, and a black crossbody purse

Wear it with: a chunky knit, a plaid blazer (similar), black sock booties (similar), and a boxy crossbody. During the winter months, don’t be afraid to layer with an oversized coat, high boots, and warm tights.

I have comfortably worn this exact outfit to a bridal shower brunch, while reaching for white sneakers, a sporty hoodie, and a long oversized coat on those casual days. Similarly, I find this cable knit midi to be more than appropriate, not to mention comfortable, for the 9-t0-5-ers and the chic entrepreneurs.

For more midi skirt options check out the faux leather skirt with tie, the dark blue pleated skirt, and the frayed button-front corduroy skirt.

P.S. I highly recommend adding this Montpellier Sweater to your F/W closet, as it is ridiculously warm and soft (no itch!), above already being stylish and flattering. I am talking feeling-hot-in-0°C-weather kind of warm. Swear it.


Patent Leather Shoes

a blonde woman sitting on a park bench, wearing a grey sweater and coat, black jeans, black shoes, and black crossbody purse
Turtleneck: Aritzia, Denim: Citizens of Humanity, Coat: Oak & Fort, Shoes: Calvin Klein

There are some that find the colour black to be boring. Others wear nothing but. Yet, both can appreciate patent leather: leather with a high-gloss finish.

Personally, it’s the colour black, just reinvented. This Fall/Winter trend takes a plain black shoe to a whole new level of dressy, polished, and edgy, all in one shot. Although masculine and bulky in nature, it has the ability to complement trousers, skirts, dark floral dresses, and even denim. Lastly, the platform adds that signature statement while maintaining the classic Oxford style.

a blonde woman posing in a park while wearing a light grey sweater and coat, black jeans, and black shoes
a matcha iced coffee and hot chocolate placed on a black coffee table in a cafe, with a woman's black shoes in the background

Wear it with: a ribbed turtleneck (similar),  dark denim, a simple black belt, an oversized coat (similar), and a structured crossbody. Pair it with the same cable knit skirt, vintage sweater, and transitional pieces mentioned in this post, for that semi-formal and polished look.

For more patent leather options check out flat-formed oxfords, low wedges, and Italian leather-lined classics.

P.S. Breaking them in at home is required, as they offer an expected structured and compact fit.


Vintage Sweaters

A blonde woman wearing a blue sweater at a Toronto cafe
Sweater: Mango, Denim: Levi’s

Some call it “colour-block,” others “80’s sporty,” while I just group this Fall/Winter trend under the term “vintage,” since a recurring trend for the past year has been recycling the 70’s through to the 90’s.

On its own, this sweater‘s bright colours, high collar, and the elastic cuffs remind you of something that your young parents used to casually stroll in back in the day. Today, it adds that fun contrast, brightening up the typical grey and black burrito outfit that we usually live in throughout the colder months. Similarly, own it as part of a full out sporty outfit or a semi-casual one, whether running errands or meeting someone for coffee.

A blonde woman wearing a blue vintage sweater, crossbody bag, oversized grey coat, and black combat boots, in front of a blue shipping container
A blonde woman wearing a vintage sweater, crossbody purse, and oversized coat, standing in front of a blue shipping container

Wear it with: Levi’s “Wedgie Straight” jeans, black belt, short crossbody (similar), oversized coat (similar), and combat boots (similar). Or pair it with a black midi skirt and a light blue button-up peaking from the collar and sleeves, for that retro professional look. Lastly, swap for a long puffer coat, longer denim, and thicker socks during the winter months.

For more options check out the two-tone quarter-zip sweatshirt, the colour block jumper, and the quarterback sweater.


Transitional Pieces

A blonde woman posing in a coffee shop wearing a grey turtleneck, a short black dress, a plaid blazer, black pantyhose, and heeled rubber boots
Dress & Turtleneck: Aritzia, Plaid Blazer: Zara, Rubber Booties: Jeffrey Campbell, Belt Bag: Ardene

This may not be the newest trend, but because of its practicality, it’s my favourite one. The best part? There is absolutely no need to spend money, only time.

The core basis of this trend lies in re-styling pieces from the previous Spring/Summer seasons. We are talking denim skirts, jumpsuits, floral dresses, and lacy camisoles, to name a few. The “transition” part not only speaks to the eligibility of that one S/S piece, but also to the other season-appropriate clothing that bring the outfit together. This includes turtlenecks, pantyhose, blazers, oversized coats, winter accessories, etc.

a blonde woman walking, wearing a grey turtleneck, a short black dress, a plaid blazer, black pantyhose, and black rubber boots
a black and white photo of a blonde woman posing on the stairs of a parking lot

For example, take this short black dress that I had purchased during a summer sale in 2017.  While it is black (a colour of choice 365 days a year, really), I have found it to be too short for comfort even during the summer months.

I was even ready to give it away, but cue seasonal closet purging, a rainy day off, and multiple trial and error try-ons.

By adding some of my go-to staples: a ribbed turtleneck (similar), black pantyhose, heeled rubber boots, a light plaid coat (similar), and an oversized grey coat (similar), I had a brand new outfit. While I may have made a mess of my bedroom floor, I did save money, extend the lifespan of my clothes, and had fun creating multiple outfits. In other words, winning on all fronts with this Fall/Winter trend.

P.S. Don’t forget to check out the “5 Ways To Summer In The Fall,” for more details and ideas on how to repurpose your S/S pieces.

P.P.S. These heeled rubber boots are only $74.00 CAD. A definite steal considering the comfort of the heel, easy slip-on, and compact fit in all the right areas.


Combat Boots

black combat boots worn with cropped denim and a grey coat
Boots: Purchased in Russia, Denim: Levi’s, Coat: Oak & Fort

Throughout the years I find myself reaching for more comfortable, practical and staple items. Quite a leap from the skin-tight dresses, short skirts, and platformed stiletto days, I must say. Glad that phase is over though…

These days I tend to express my style with more casual minimalism and masculine-inspired footwear. Cue the comeback of a combat boot, with that kick-ass feminine edge, for our last Fall/Winter trend.

These boots are a frequent match with my dark denims, midi skirts, and dressy blouses. They excel at ‘toughening’ up any S/S transitional pieces, such as long floral dresses and denim skirts, while taking semi-formal wear from night to day. Similarly, their tall and slim ankle fit invites an elongated-leg look and allows for an oversized statement jacket to look appropriately proportionate.

A blonde woman wearing a blue vintage sweater, crossbody bag, oversized grey coat, and black combat boots, in front of a blue shipping container

Wear it with: a vintage sweater,  Levi’s “Wedgie Straight” jeans, black belt, short crossbody (similar),and an oversized coat (similar). Similarly, style it with this faux fur coat and a long dark floral dress for a fun, and super comfortable, night out.

Lastly, find a boot that matches your style: a minimalist ? Try these. Looking for that extra edge? Reach for these. Want to be warm and stylish? Pick these up.



There you have it! These 5 Fall/Winter trends are my current go-to’s for anything from semi-formal to casual chic. The best part? Their practical, versatile, and affordable nature compliments many outfits (and wallets), as well as each other (e.g. midi skirt & patent leather).

Hope you enjoyed this style post and won’t hesitate to share your go-to trends for this Fall/Winter season.

P.S. Which look was your favourite?






  1. Marysol
    November 29, 2018 / 10:39 pm

    Great post! Will definitely be adding some of these pieces to my wardrobe!

    • arina
      December 7, 2018 / 3:56 pm

      Thank you Marysol! Glad you enjoyed the post. Thanks for stopping by. 🙂

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