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Wonderful Winter Style Inspiration For You
❄️❄️❄️ Here comes a collection of wonderful winter style inspiration to keep you looking great in the cold weather. Stay warm and stylish all winter long with the best cold season fashion advice from your personal stylist + Play FREE This or That -style game ❄️❄️❄️
Winter Edit of This or That -Style Game
To give your winter style some serious panache, I created a winter edition of the popular This or That -style game. You might remember the rules from the previous editions already. I am listing them here so you can go and look back (or reuse) at some great style moments:
As your personal stylist I want to encourage you to experiment with your style so you can find the items, shapes and colors that suit you the best. Have fun and take some fashion risks. Don’t hesitate to invite your friends to do the same. This game is a perfect way to start!
How To Play This or That -Style Game?
- You need a pen and paper to write down your choices.
- This game can be played literally anywhere.
- Play this game alone or with a friend.
- Choose an option from the left or right column and write your preferences down.
- Once you have gone through all the options, you’ll have a complete look to wear.
- Play the game soon again. Your style preferences can change from day to day.
Winter Style Inspiration Curated by I On Image
1. Chic Layering
Layers are the key to staying warm. Get warm long sleeved undershirts and leggings to keep you nice and toasty. I love thin merino wool tops, sensual bodysuits and soft polo necks. They layer nicely under sweaters, cardigans and even blazers.
I like to pop a long sleeve turtleneck under a dress. That way I can keep on wearing dresses even when it’s cold outside and I get the most out of my wardrobe all your round.
Turtlenecks – Long sleeve and Sleeveless
Leggings – The Cozy and The Sexy
2. Cute PomPom Hats
There is no point freezing your greatest asset, your brains, when there are so many amazing options to choose from. Get a stylish hat or a headband that suits your style and face. Finish off your winter look with a matching scarf and gloves.
I love these Sh*t That I Knit customizable wool beanies with removable faux fur pompoms. You can change a new pompom based on your mood or take it off when you need to wash the hat or you are wearing a winter sports helmet. Very handy!
3. Warm Heritage Knitwear
Invest in quality knitwear and learn to take good care of them. Consider buying vintage because the quality of knitwear used to be better back in the day. Some of the pieces might last a lifetime, which is a promise the current high street is too often unable to make.
This season I am in love with heritage style fair isle designs, cozy cable knits and retro vibe jacquard sweaters. I wear mine with a pleated skirt or thermal leggings (see point 1.) and add a cool boot (see point 4.). There are so many styles to choose from. Don’t be afraid of a little color, it will improve your mood during the dark months.
4. Cozy & Cool Boots
Get high quality winter boots that keep you warm and grounded. Pay attention to the sole material and choose a warm lining. If it’s snowing or very icy out there, you might want to consider leaving your heels at home. Broken or twisted ankles only hinder your success unnecessarily.
I have been waiting forever for the shoe fashion to become wearable. It looks like our dreams have finally become true because comfy footwear is finally en vogue. You can still have toasty toes without sacrificing the style. Let’s not ever feel cold again!
5. Proper Tights
Swap your sheer tights to thicker deniers, such as 60d or even 100d. Consider styles made of lush merino wool or cashmere mix. There are also plenty of thermo leggings that look fabulous under dresses.
Wide floaty pants get a longer shelf-life with a warm panty hose worn under. These styles are no longer reserved for the warmer months. Layering really increases the use of of your wardrobe and makes it more sustainable in the process.
7 Best Winter Materials
- Wool: Merino, cashmere, silk wool and technical wool fleece
- Classic heritage fabrics such as tweed and plaid
- Chanel-style chic bouclé
- Velvet and velour
- (Faux) fur, especially in jackets
- (Eco) shearling also as a shoe or glove lining
- Quilted and puffed styles for outerwear
TOP TIP: Remember to take notes of your best looks so that you can repeat them when needed. This will make your mornings so much easier. It’s like having your own daily style cheat sheet!
My Personal Styling & Shopping Advice For You
Ask for style advice in the comments section of this post. I’d love to answer your questions and to help you get better style with less effort. This will cost you nothing!
Don’t forget that if your budget doesn’t stretch to a personal shopper right now, you can always shop my style on LIKEtoKNOW.it shopping app.
This is an affiliate program and I may earn a commission from your purchases. There is no extra cost involved for you and all my recommendations are based on my personal fashion preferences. Thank you for supporting I on Image!
Go shopping with a Personal Stylist! Read more about my personal shopping services in Amsterdam or shop with me online! Hiring a professional Personal Shopper is such a time and money saver + It’s a lot of fun, I promise!
Please share your best kept winter style secrets in comments. I am curious to hear how you manage to stay so chic in sub zero temperatures.
This post was originally published on 6th January 2020 and updated on 20th January 2022 with fabulous new items for you to shop!
❄️❄️❄️ Stay warm and stylish all winter long with I on Image ❄️❄️❄️
43 thoughts on “Wonderful Winter Style Inspiration For You”
Thank you so much for the lovely feedback! I am glad you enjoyed my winter style post xx
I’m all about the layering! And yes, boots & knitwear are my go-to this winter! Loved the game too x
Me too! I a now working most of the time at home and it can get so cold when sitting down all day. Stay warm and hope your pain stays at bay xx
I love knitwear! I have recently brought two new jumpers and I love how cosy I feel. Layering is a must as I can’t get cold as it makes my pain worse. Thank you for sharing your suggestions.
Lauren – bournemouthgirl
Very happy to hear that you enjoyed my post! Here’s to a very stylish cozy season xx
I loved the ‘this or that game’! I went through each choosing my favourites. I must say Winter is my favourite month for fashion.
Oh yes! Long cardigans are the best for cocooning in style xo
I’m always about the long cosy cardigans!
Yay, left column it is then! Sweater weather is my absolute favorite because of all that coziness and wholesome hygge-vibes. Agree also that, yes, those boots need to be comfy. Otherwise it’s not worth it in my opinion. Hope you’ll find a lovely pair!
The This or That games are so fun & I would personally pick all the items on the left haha
I do love the colder months because I can pull out my sweaters & I recently bought a pair of 120 denier tights so I can stay warm while wearing dresses
I would like to get a new pair of boots because the pair I have aren’t that comfortable to wear.
You are most welcome Charity! Enjoy the cozy season in style xx
This is definitely inspiring my winter wardrobe coming up! Thanks for sharing all these ideas!
Thank you so much for your sweet comment Elle! I too love the cozy season a lot xx
Some real great style advice here! I love winter fashion, it is my absolute favourite. Thank you so much for sharing Xo
Elle – ellegracedeveson.com
Thank you so much for the encouraging comment Jenny! And good point about the Instagram stories. I need to pop it in there too with the new story link function that I am super excited about 🙂 Have you tried it yet?
Great post! Some excellent style advice for Winter and I love playing those this or that games on Instagram stories!
I LOVE your winter style so much Quinn! Thank you for reading and being my fashion pal xx
I loved reading your blog hun and you’ve made me think about my own winter staples; cable knit tights (warm, yet fashionable), beret hats (as I have a fringe and bobble hats don’t work with my hair unfortunately) and mix and matching skirts with jumpers/high neck tops.
But have some material to make myself some fabulous 1940’s style overalls and trousers!
Thank you for another fabulous post!! ☺️
Glad to hear that you got inspired by my post xx
This definitely gives me some winter style ideas! Thanks so much for sharing them!
Thank you for mentioning that Lynn! I am also always cold but I love dresses. The key is in clever layering. I have more ideas in this post for you https://ionimage.nl/extend-the-life-of-your-summer-dress/ Stay warm xx
I love that look Anika, thank you for sharing! Enjoy your fabulous winter style and stay warm xx
Dressing for winter has always been so hard for me because I’m in love with dresses but you’ve got some great suggestions! Thanks for sharing x
Great post, love the tips! As for this and that, I’d go with bobble hat, puffer jacket, hiking boots, long cosy cardigan, wool mittens, and pleated midi skirt!
Anika | chaptersofmay.com
Oooh that sounds lovely! Hope your birthday wish is fulfilled Lisa xx
Love this game, Jenni. I am definitely the RH category for most of the pieces and a butter soft A-line leather skirt is top of my wishlist. It’s my birthday next month so I have high hopes 🙂 x
Great to have you here Amber! Glad you got inspired by those hats. I love them too xx
Thank you Emily! Delighted to hear that you found this post inspiring. Stay tuned for more xx
omg, how cute are all these hats! I never normally wear hats but I think I will have to give it a go!
Amber | The Unpredicted Page
Oooh this is a fun idea! Thank you so much!
Oh no! A broken boiler in January is bad. We had it a few years ago and it was freezing in here. Hope they can fix it soon for you. Until that, stay warm xx
I’ve rarely left the house over the last 9ish months so my style doesn’t seem to matter at the moment, but the boiler has been broken at my place for a month now, so wrapping up is annoyingly important at the moment
Thank you so much Tea! Happy to hear that it inspired you xx
Love the game 🙂 Definitely need something like that to get more inspiration for my winter combinations 🙂
Yes indeed a very mild winter this year. I am always cold so already wrapped up since November. But I don’t need as many layers as I would in my home country Finland, for example. In Helsinki it has been very mild this year too and hardly any snow.
It’s been pretty mild so far this year but just waiting for the first wintery blast so I can get my favourite hat and mittens out!
Thank you Sophie! Glad to hear you enjoyed this post xx
I love so many of the fabrics you mentioned here and the general cosiness of a winter wardrobe. The game is always fun to play! x
Thank you xx
Thank you so much for playing Lauren! Stay warm and cosy xx
Such a interesting game! Thank you for sharing!
So happy to hear that Madi! I also like both sides and can’t choose, so I am changing my outfit every day -just because it’s fun and I can xx
I love this game, I have to say I like both sides (other than the ear muffs:) I am so on board with you regarding dressing for warmth, layiring can be fun.