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How To Dress Like A Tomboy - Holiday Outfit Ideas


Look 1




Let's start things off with a high-end city look! This outfit is great if you love simplicity and classic styling.

Black and white combination is a great choice for most occasions and holiday gatherings are no different. (Unless you've been invited to an ugly Christmas sweater get together...but since this is a blog about helping you dress well and stylish, we won't go there.)

Black pants, white long sleeve textured top and long black coat is the simple, yet impactful ensemble here. You could use black boots, but the light coloured Chelsea boots create more of a statement and add a bonus layer of the effortless elegance that I naturally gravitate towards. 

If you follow me on Instagram, you know that silver watch on one wrist, silver-black Live Dream Love bracelet on the other and silver rimmed aviator sunglasses are my go-to accessories.

These three items combined keep things simple, stylish and in this case match the silver zipper and buttons on my coat, perfectly tying this dapper Tomboy look together.




Look 2



Sticking with the black and white combination, this is a more relaxed and on trend look.

I've kept the black pants and beige Chelsea boots for the bottom portion of this outfit and switched out the colour combination on the top portion.

The base layer is a textured long sleeve black shirt, while the outer layer is the currently trending jersey shirt jacket with large pockets and snaps. This is one of the handful of new wardrobe investments I've made this winter and I truly love the versatility of this piece! It can be worn as a shirt, mid layer or a jacket and I know I'll get great use out of it.

The material, cut, colour and overall styling of this jersey shirt also strongly remind me of some items in my ultra-stylish Grandma's wardrobe, so wearing this piece definitely has a sentimental meaning to it as well.

I tend to pop the collar and roll the sleeves on all of my casual shirts for extra style and this shirt is no different. You can of course "keep it proper" if the setting calls for it, but for me, this brings some of my free-spirit personality into the outfit.

And as you can see I've also kept my go-to accessories, bracelet and watch.



Look 3




Switching things up, we move onto the first army green chinos combination.

I've kept the same Chelsea boots to show you just how useful it is to invest in a pair of high quality, stylish, comfortable boots for the winter. 

It is equally important to invest in a high quality, stylish jacket in a colour that will match numerous outfits - black is a great choice both style-wise and for practical reasons. You can of course purchase several different styles and colours, but I prefer to invest in fewer pieces I truly love instead.

What screams holiday style about this outfit, is the shawl collar sweater. I love details and it is the detailed pattern of the weave and the toggle button that made me fall in love with this sweater. I also love the marled yarn and the unique grey colour it creates.




And yes, the triple accessory combo of silver watch, silver-black bracelet and silver rimmed aviator sunglasses also works here, complimenting the silver details of the jacket!

All in all, this is a sharp looking, functional outfit that will make family introductions a breeze!



Look 4




This outfit is another smart, polished way to style the army green chinos and black jacket from Look 3.

The tan dress leather boots elevate this outfit to the next level. And the traditional argyle pattern of the V-neck sweater creates an interesting contrast with the ultra modern motto jacket. 

The colours work together nicely and unify the whole outfit into one that is sure to gain instant approval from even the most critical members of your Boo's family! 

The one other extra sharp detail of this outfit is the crisp white T-shirt underneath the V-neck sweater. Some people will argue against the crewneck underneath the V-neck, however, this is how I prefer to style it both for looks and warmth.



And yes, you guessed it - my go-to watch and bracelet accessories remain, though sadly, for this photoshoot I had to switch the aviator sunglasses for an umbrella.  



Look 5




If you prefer a more casual look, going with a well fitting pair of dark denim jeans is always a great option! And while distressed and torn jeans might have a certain appeal to them, keep in mind the occasion and opt for a solid pair of jeans in good condition.

This outfit features the most lightweight of the three sweaters shown here. But being made out of merino wool, it is actually the warmest one of the three.

I style this sweater with a collared shirt and make sure to have the sleeves of the shirt poking out a little bit, so the wool doesn't irritate my skin. I do actually love the aesthetic this creates and it also works well with my preference to wear my shirts untucked.

Another thing to notice about this outfit is the tasteful stripe pattern. Stripes are a classic and a simple way to break away from just plain solid colours giving your outfit that little extra point of interest.

The Chelsea boots make a re-appearance for this outfit to keep it up to par with the significance of the occasion and making that all important great first impression.

Accessorize tastefully to complete your look!



Look 6




Last, but not least, here is a look you can try if you are really feeling adventurous and confident in your abilities to charm the relatives!

Every piece of this outfit makes a statement and if you can pull off a combination like this, your family introduction will definitely be a memorable one! 

While most of your peers will be wearing a sherpa lined jean jacket or aviator style brown or black sherpa jacket this winter, only someone with a refined taste will invest in a light-coloured standout piece like this.

Fashion choice like this directly reflects on your discerning taste in other areas of life. In other words, it will be seen as a compliment to your significant other and their family because of all people, you chose to lavish your affections on them!

Likewise, it is highly unlikely that anyone in your vicinity will come across or be willing to invest in this utterly unique Seafarer brushed cotton twill shirt.

Nor will anyone likely think of combining these statement pieces with the notable light brown chinos pictured here.

And let's be honest, most people would likely opt for black combat boots to finish this look with, but you will know better and keep it refined and stylish with your light-coloured Chelsea boots.




And so there you have it! Six complete Tomboy outfit inspirations for the Holidays and the big occasion of meeting your Boo's family for the very first time.

Which one of these is your favourite style? Let me know in the comments below!









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