20 Winter Outfits For When You Don't Know What To Wear

1) Layering 101 If you live in Antarctica or someplace as cold as my country can get, here are my ultimate tips on layering: start with that skin tight layer. Tights under your pants, tight shirts under your regular one. Layer sweaters and jackets, wear long-sleeves under short-sleeves and don't be afraid of dresses and skirts! I think this velvety graphic tee is complimented by the stripey long-sleeve underneath.

2) The Rules Of A Chic Sweater In winter, everyone just wants to bundle up in a giant sweater. Great idea, but I have a few ideas to keep your sweater cute. I don't own an Ugly Christmas Sweater (UCS) but I do like my sweaters to be a little fun and not plain. For something a little more stylish, this nautical-striped one is classic and chic. When I bought it I thought the gold buttons on the shoulder were such an interesting detail, and I still do! I chose these velvety pants, and I think this is very Parisian and Coco Chanel.

3) The Rules Of A Funky Sweater If you want something a little more quirky I love this one, which is two-toned with different-coloured sleeves. My go-to winter outfit is a sweater and jeans, but since sweaters are always kind of loose and bulky try to contrast them with skinny or straight leg jeans. Also, I kind of like how the sleeve of my sweater is pointing at something - I don't know what, but its kinda funny.

4) Contrasting Coats & Clothes I had to get a new winter coat this year, and I chose this uplifting lilac colour. I think it's surprisingly a colour that goes well with everything, since my jeans are all navy, my snow pants and boots are black and my hat, gloves and scarf are neutral. However, no matter your jacket colour, an easy way to look chic and coordinated is to match all your hats, scarves, gloves, etc. If you have a black coat, red accessories would be gorgeous.

5) Dresses And More I love dresses, and I hate when people say "oh, you can't wear a dress in the winter!" Not true, it just requires some extra work on your part. Layering is the key. I always wear leggings under my dress in colder weather, but in case you haven't realized leggings are super thin. You could try layering tights underneath your leggings for a skin tight layer. That'll keep you toasty! Add a sweater over your dress for some extra warmth.

6) The World Of Long-Sleeved Dresses However, I happen to own a lot of long-sleeved dresses. I think they look really nice, and some of them are even made out of sweater material so they're warmer than you might think. You've seen this dress before, so I tried to change it up with a kind of punked-up belt. Make sure to wear a long-sleeved shirt under your dress, and you're good to go! 

another outfit w. this dress

7) Sleeveless Shirts Do you have a sleeveless top that you love, and wish you could wear in the winter? Most of the shirts I've sewed are sleeveless, since it's quicker and uses less material. This one is the perfect balance between my two main styles - girly/kawaii and edgy/city-chic. I wear it with first, a white tank top tucked into my bottoms for that skin-tight layer you always will want. Next I add a long-sleeved shirt. I chose this red one that matches the print. Now I add the actual shirt I want to style, along with a fuzzy vest. There! Nice and warm.

8) Two Jackets? Oh My! My favourite piece of clothing ever is my moto jacket, which you've seen so many times. Obviously, I can't use this as outerwear right now but I can use it as a sweater. Not the most comfortable sweater, okay, I get what you're thinking but this is how i wear jackets year round. I think a lot of people don't realize that you can just layer a jacket under your winter coat! Wow, Captain Obvious here.

9) Pants That *Aren't* Jeans I have these plaid pants, and they are getting to be pretty small for me but no one can tell in a blog post. I thought these would go great with denim, so I chose an equally preppy jean jacket. I think 

10) Am I A Fabric Nerd? The next few outfits are all about fabrics and necklines. I like to contrast my look with the colours, but the materials of the clothes itself are an underrated idea. The holidays aren't in a while, but everyone else is getting in the spirit so I will too. I want to do a whole holiday lookbook, but here is a sneak peak. I think black and white is classic, and layering this soft white cape over this dress has the faux fur, tulle, satin, rhinestones and cotton going for it. I think this looks super posh and luxurious.

11) We’re Talking About Necklines Now I thrift-flipped this v-neck knit sweater. I like that despite being so chunky, it has a defined shape. I don't own anything else with a v-neck, but I like how it looks with a regular top underneath. I went for a stretchy and tight sweater underneath. I feel like I use necklaces a lot to make a plain top not look so boring, but I won't need a necklace wearing this outfit!

12) Fancy Me This might be a little fancy for most folks, but for me there are two levels of outfits: extraordinary-princess fancy, fancier than the royal family, and over-the-top casual for most days. This falls under the second category. I chose my leather skirt and added this cropped blazer. I like they're both pretty structured pieces of clothing, but nothing looks stuffy. 

13) An Interesting Combination Try wearing a wrap skirt over a bulky or pullover sweater. This might be a simple tip in this blog post, but I think it's a cool combination. 

14) My New Leather Jacket! I got a new leather jacket. Eeee! I definitely love my other one more, but this is a little less cool girl and a little more hipster. Leather is supposed to be in style now anyway, so there's that. I wanted to challenge myself styling it, so I went for an orange knit sweater underneath and rhinestone jeans. Contrasting fabrics AND colours! I think the super big jacket works with the super skinny jeans.

15) A Modern-Day News Gurl This coat isn't as warm as my lilac one, but for those rare sunny days it's perfect. I remember one Christmas years ago and it was 15 degrees! (Celsius, of course.) I've put this coat in my blog before, but it's always been styled in a traditional preppy way. However, I wanted to change things up today so I'm dressing it down with my beloved star jeans.

16) Slightly Questionable Style One thing we've been seeing a lot of lately fashion-wise (one of the pressing issues in the world, I know :) is layering collared shirts under hoodies. I do think it's kinda cute, although it's funny that people are trying to dress like a private school girl on winter break. I chose to do something a bit different by layering it under this charming sweater. It used to be a dress, but now it fits me like a regular sweater so that’s cool.

17) Not Disgusting Puffers Puffer coats are classically trendy. They aren't my fave because they either make you look like an artificial candy or a giant sumo wrestler, but you can find the ones that are the perfect in-between balance. I like that this pink one is puffy, but instead of that kind of "bubble" look you see most often its quilted. Quilted jackets are apparently on trend this winter (who decides these things?) so for you trendy gals here you go.

18) A Story About My Shoes I don't know how many people actually wear heels in winter, but I love these heeled booties. Just make sure they have a block heel, some traction and aren't too high. Quick little story about these shoes: I wear these to school sometimes and when I wore them once last year this annoying boy at my school (shoutout to you, Adam!) dumped this disgusting green smoothie all over me and I had to go to the school bathroom and try to scrub it off my clothes with one-ply school toilet paper. You can still see the stain. Sigh. 

19) Have You Ever Seen A Cooler Coat? In my last blog post, "Ten Ways To Style A Dress" I featured this coat my mom had picked up from the nearby consignment store. This design is so extra and I love it. I wantesd to show it off again. Look at the way the ribbons tie through the grommets! Who thought of that? Sew cool. I paired it with those velvet pants from before. This look reads as monochrome, but a pretty nice take on it!

20) Don't Tell Me This Isn't Cute  Fashion secret here: flannel shirts aren't actually that warm. I know, right?! I wore this pink one over a black pepper-and-salt sweater, along with some pink pants. These pants are thicker than leggings, but equally as comfy so they're a must-have. And yes, there is a big stain in the leg but these are my sister’s. I like this flannel since it screams cutesy a little more than lumberjack. Pink and black is either emo or girly, but I have to say I like the combination!

Those were my twenty outfits! If you made it to the end, give yourself a pat on the back. By for now!

20 Fall Outfits For When You Don't Know What To Wear


  1. Which looks were your favourite? Thanks sew much for reading!

  2. Hmmmm. It seems when I leave a comment here from my phone it doesn't get through.
    So here you go. I just love your sense of humour. It's a great part of the total experience following this blog.

    1. Thanks! And yes, commenting has a lot of technical difficulties sometimes but it almost always seems to work on a laptop or computer. Thanks for reading

  3. It’s snowing today!!! Got this blog post out just in time ❄️

  4. I am definitely enjoying your website. You definitely have some great insight and great stories.
    Tv Series Leather Jackets


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