Tomboy Outfits for Fall/Winter Fashion - 3 Ways To Style 1 Tomboy Outfit Tutorial

Depending on how you look at it, Fall/Winter season can mean either a lot of fun or it can be really dreadful when it comes to staying fashionable.


Fun, because you get to play around with many different layers and accessories. Dreadful, because you have to find a way to stay warm if you live somewhere where temperatures plummet mercilessly this time of the year and that ain't always pretty!


To help you out, here are 3 ways to style 1 Tomboy outfit during this transition season that will give you ideas on how to get through Fall/Winter 2020 in style!




Let’s start with Look 1 - the corporate version of this outfit, since this is the one I started with.




The base of this business outfit are the plaid print pants in black, white and grey colours, along with the cream white ribbed long sleeve shirt. While the tailored fitted pants with tasteful and classic pattern provide the structured component of this base outfit, the slightly oversized sweatshirt-like top adds that laid-back, unorthodox look and feel. The ribbed texture of the top and its off white colour distinguish it from just any old sweatshirt and give it an unpretentious look of luxury. 


You could, of course, easily substitute the top for a turtleneck, sweater or combination of dress shirt and sweater to create multiple variations of this outfit. Same goes for the pants, where you could easily substitute different patterns and colours to achieve similar effect.


Black and white are undisputed classics suitable for any occasion though, which is what makes this a great base outfit to play around with.


So what then gives this version of the outfit its sharp and commanding business look?


The answer is the well fitting long black coat and tan dress boots. The black coat is the centre piece of this outfit and it is what gives it its formal appearance. And while the black and white colours reaffirm a sense of tradition, the bright tan colour of the dress boots adds a sense of flair and daring fashion sense.


The accessories used are my three go to choices. Large silver-white wrist watch, silver-black Live Dream Love bracelet and silver aviator glasses. All of these simply and easily add even more class to this look.





Moving on to look 2 - the most versatile and the warmest version.




The base outfit stays the same, giving countless options for the wear of this outfit. Styled this way, it is equally appropriate for office wear, day-to-day city adventures or a mountain cabin weekend getaway. For me, this would definitely be my choice for a Festival of Lights date night.


You’ll notice that I’ve kept the colour combinations from my corporate outfit same. I did this to emphasize the point of how much difference the cut of a jacket and boot profile make. These two elements alter the entire outfit in this case!


The waist-length puffy down jacket compared to the long coat makes this version of the outfit less formal and gives it a more versatile appeal. Function wise, it is also more versatile as the addition of a hood makes it a fantastic option for even the most adverse weather conditions.


The full-on winter boots play to this theme of warmth and protection of elements as well. Tucking the pants into the boots eliminates any potential draft or snow getting in, which if you live in places where this matters, you know it really matters a lot! The boots are waterproof and lined for added warmth. Even visually, they are more robust than the dress boots used in outfit one, which balances well with the more bulky appearance of the down jacket.





Last, but not least, look 3 - the lightest and the most light-hearted version.




I have to confess that keeping the base outfit for this version took quite a bit of mental gymnastics for me! I don’t know about you, but my upbringing involved having play clothes and dress clothes. One, I was a very active kid who paid no heed to obstacles such as puddles and two, wearing dress clothes was tied to important occasions and celebrations.


So keeping the same shirt and pants that I previously associated with a business outfit was quite a mental shift when styling this fun outdoor one!


But like any leftover childhood conditioning, once I faced this preconceived idea of what is and isn’t appropriate outdoor wear, I found this view of clothing doesn’t serve me and I was able to let go of it, replacing it with my own belief that clothes are clothes - they are a tool, a means of self-expression and an outwardly reflection of the value I place on myself. And most importantly, even if it is difficult to find clothes that fit my idea of style, comfort, quality and coolness, they are replaceable and I am fully in control of deciding when I get to do that.


Because yes, it was partially sense of respect and occasion that has kept my wardrobe compartmentalized in this way, but there was also a leftover scarcity mindset at play here. It was all those negotiations of getting to wear blue instead of pink and those rare moments of getting the kind of clothes and shoes I wanted to wear, instead of the kind that society dictated for my gender and which my family wholeheartedly embraced.


If you’ve ever experienced this kind of deep introspection while styling an outfit, do let me know in the comments! I’m sure a lot of you can relate to this kind of struggle of self-expression growing up and I’d love to hear your story of how you faced these limits placed on you and how you outgrew your own self-limiting beliefs!


Getting back to the topic at hand, I am happy to report that while I certainly had fun and did not restrict myself from any movement or activity that day, the outfit remained pristine and unscathed. And I was actually amazed at how comfortable and genuinely happy I felt the entire time!


Let’s break down what makes this styling so much more casual and fun.


For starters, the laid back, slouchy beanie instantaneously gives this outfit its relaxed vibe. As much as I love to style my hair perfectly, beanies are an inevitable part of the Fall/Winter season when you live in Canada and to lessen this necessary evil, so to speak, playing around with different styles of beanies is definitely an easy way to alter your appearance.


Next we have the pulled up sleeves and puffy down vest. This is both functional, by accommodating ease of movement while still providing adequate warmth, and fashionable, because who doesn’t love the somewhat rugged outdoorsy appearance of the classic North Face down vest, boldly proclaiming that its owner is mountain-adventure savvy (at least true in my case!) and the always sexy rolled up sleeves styling showing off well-defined, strong forearms surely capable of some great feats! (Also true in my case.)


Last but not least, I opted to cuff my boots for this outfit to reinforce the overall laid-back vibes and to give the pants a more relaxed appearance with the imperfect tuck-in into the boots.




So, there you have it! 3 ways to style 1 Tomboy outfit to give you ideas on how to stay stylish, fashionable and warm this Fall/Winter season!


Leave me a comment below to let me know how you will use this inspiration for your Tomboy outfits and tag @hld.light in your Instagram posts if you decide to share your outfits with the world!




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