How to look CLASSY in Winter 2019

How to dress classy in winter? That is a good question. Do you know how it is to try and look good in like -25 Celsius degrees? It’s not easy. I know because I grew up the hard way. Welcome to the School of
Affluence YouTube channel. My name is Anna and I run
the School of Affluence which is an online
finishing school for women who want to become more
elegant and navigate more successfully in the high society. Now let’s level up girls. Let’s talk about winter fashion. This topic is very close to my heart because I live in a Nordic country. I grew up in a Nordic
country and God knows if I will stay in one
for the rest of my life. Maybe that is my karma. I wish I was a little bit
more southbound somewhere, but to be quite honest with you,
I do enjoy the seasons. I think the seasons are cozy. The only problem is
like it’s not very cozy when it gets too cold because that creates a big problem for us. Like how are we gonna look chic? How are we gonna look elegant and so on? But I’m gonna give you a few pointers that I want you to focus on these pointers
now during winter season. Now, when these winter sales starts and really try and purchase these type of items because they are going to elevate your look in winter and it’s a bit like a fast track to look
expensive and looking classy. Now let’s cover one
important basics first, and that is if you live somewhere that is let’s say, one meter of snow, it is -30 degrees and you
don’t have a car, and you wanna wear
heels and you wanna wear like a nice dress, it’s going
to be impossible really. There is a level to what you can do and achieve during winter and depending where you live. I say that in winter time, it is worth spending more on taxi. I know that not all of you ladies have a big budget to
spare but if I was you, I would prioritize a bit of taxi so that you can look
better than having to take, I don’t know the bus or
something or walk. Oh my God, walk. Imagine walking with your
cute little dress and stuff. No, invest in taxis because this is the time of the year where we’re not supposed to be
stingy when it comes to taxi. If you wanna look good it’s going to cost. That’s just the way life works. Okay. Moving on. That was the basics. So, girls take taxi, that is my advice. Now, the number one thing that everybody, everybody needs to invest in and that is a gorgeous expensive coat. Okay, it doesn’t have to be expensive but it has to be like expensive looking. And the reason for that is number one, the coat is a big piece. So, the bigger the pieces,
the more it stands out, the more space it takes on your body, the more you have to spend on it because people are going
to pay attention to it. Number two, a coat that is
of high quality materials will be much more warmer than some coat that you bought at Zara. But I need to give you to advice though. I want you to buy two colored coats. So, I want you to get one in black, because we all need a black coat. This black coat you should be able to wear during the day
and during the evening. So, you can alternate it. You have to find a coat that is all round. A coat that works with your daytime outfit and with the evening outfit. Now, secondly you need to
buy a light colored coat. That coat can be maybe
white, off white, camel. Camel is a very good choice, maybe light pink. I don’t know, it’s up to you. This coat would maybe be more for daytime. You can also of course wear it during night but I don’t know. Somehow I’ve always
found that lighter colors just look a bit better during daytime, but that’s just my personal preference. Now I’ve spoken already about monochrome and I will be talking
again about monochrome. You see, one of the most clever ways of looking like high
fashion, elegant and classy in winter is to be layering in monochrome. So, whenever you layer in monochrome, it’s not going to look, I don’t know, messy. It’s all going to look very united, and when it looks united, it just ends up looking a little bit more high fashion. So, I don’t know. Choose a color. Maybe not black. Maybe, I don’t know, beige, camel, white. White is always a safe bet if
you wanna look very expensive, especially if you wear
an all white outfit. Now, it’s not the first time I say this and this is not going to
be the last one either. If you’re feeling a little bit bold, you can go maybe all red. I don’t know. You choose but layering in the monochrome is definitely going to keep your warm and make you look high end. Riding boots, riding boots, my favorite. Oh, I love riding boots. I have this big, I don’t know, passion for equestrian fashion. It may be because I’ve been
a horseback rider myself for like, I don’t know, 15, 18 years. So, perhaps, yes, I will be a bit bias, but I love, I love like horses,
stables, equestrian style. I just feel like it looks very old money, and the perfect thing is that when you wear riding boots during winter, you can put some thick cashmere socks in those riding boots that will keep you warm and that will make you be able to walk through snow, in like really harsh climates
and you’re actually fine, and on top of it you look chic. Now, I think the most popular riding boot is definitely the Hermes one. I love the black one but I
also love the light color one. Okay, party time. Party time means that
we have to wear a dress. Anything at night or
maybe a social function, even during daytime that requires
you to put on some heels, put on a dress, but listen, it’s cold. This is not the right time
to wear that mini dress, to wear that sleeveless dress. This is the time to wear
the long sleeved dress, to wear the dress that actually
covers you up quite a lot. I’m sure a lot of you find these type of dresses to be a bit too
boring and too conservative. In my personal opinion,
I love these type of dresses. I think they’re so incredibly
chic and you don’t end up looking like a grandma
because number one, you’re not a grandma. You’re a young, beautiful girl and if you style it correctly, if you wear some nice heels, if you carry yourself with confidence, move with elegance, you will
just look very sophisticated and you will look like you’re not the one who’s trying too hard by wearing like all the skimpy short dresses and so on. And what I really like about these type of like conservative dresses is that, especially now during this festive season when we have Christmas lunches, Christmas dinners, I don’t
know, parties with relatives and grandparents and maybe
bosses and stuff at work, now is the time where we actually need to be looking a little
bit more conservative. We can’t rock up in a
tight bodycon midi dress eating Christmas lunch with our in-laws. Do you know what I mean? We have to look representable. We have to look appropriate
and I just think that now is such a good time
to wear dresses like this because you are just gonna
benefit from them really. Plus, they’re gonna keep you a bit warmer than the usual little mini dress. Now my personal favorite, the one that I’ve been
overusing for the past, I don’t know, X amount of years, that is the over knee boots. I have actually made a blog post about it on my blog JetsetBabe. See the link in the description. But over knee boots, it
is such an amazing boot because it really keeps you warm and if you wear over knee boots
together with a long coat, you’re going to be covered for wind, you’re going to be well protected and you can choose if you want to wear over knee boots
with heels or without heels. It all depends on occasion. My advice is to invest in
both so that you have options. Okay, I think I lied by the way. I don’t have just one favorite. I have like hundreds
of favorites. Okay, my second favorite
is the turtle neck. Now, I am obsessed with turtle necks, and turtle necks are amazing in winter especially if you have a
turtle neck in cashmere. If you don’t have money
to spend on cashmere, actually you can just buy
a simple one from Zara. They are going to keep you warm as well. It’s just that the cashmere ones tend to keep you a little bit more warmer. So I do see them actually
worth the investment. You won’t be needing to layer up as much underneath your coat if you wear a turtle neck of cashmere. I definitely recommend
to get a black one, a beige one or camel one,
definitely a white one as well, maybe even a gray one. I think these colors
are literally the basics and everybody should stash up on them. And now during the sale, try and buy as many turtle necks as
possible in cashmere. Trust me, they’re going
to be like 50%, 60%. Make use of this. This is a long term investment. You can do so much with turtle necks. You can even wear them in the
evening for nice dinners if you wear them with a
nice tweed skirt or something. There are many ways to spice
up a boring old turtle neck. Don’t think that just because you’re not showing any cleavage, guys are gonna not be looking at you. Trust me, they will because
you are going to look like a very sophisticated old
money woman wherever you are. So, when I was growing up,
I don’t know if you had the same thing when you were growing up but your parents always
telling you where’s your hat? Wear a hat. You can’t leave the house without a hat, whenever it was cold. I do understand now though why. Because actually,
all the heat from your body kinda goes away from your head. So, if your head is covered, that means that your heat will be like preserved inside your body. Use this to your benefit. Invest in a nice chic hat, especially a hat that really
will elevate your whole look, like make you look more glamorous. But not only will it make
you look more glamorous, you will stay more warm
thanks to that little hat that is just like saying stop to the heat not to escape your body. Win win situation, right? Same thing by the way with scarves. Scarves you can do so
many things with them. You can tie them around your
throat to keep them warm. You can even tie them around your head or any creative way that you can think of, use the scarf for that. I have also created a
blog post just on scarves so I will also link this below. Now before we continue by the way, because I’m sure that you wanna know what else I have in the pipeline for you but I want to tell you that
I have created a cheat sheet. A cheat sheet that you can
just have a quick look at if you do not know how to dress yourself so that you look classy and expensive. This cheat sheet basically
tells you in a quick way, okay, do this, do that, don’t do that. To obtain this cheat sheet,
go to The link is here and yeah, download. So, winter time means going
out at night during winter time can of course become a very cold story. Yes, you can wear those
small dresses if you want, but I would personally
advise to focus on wearing more like jumpsuits, trousers, suits in general in winter time because they are just more covering and will keep you more warm. Keep the dresses, like
keep all the dresses for summer time when it’s warm, when it’s appropriate weather. Just focus more on these type of looks, and anyway you’re gonna end up looking so much more chic this way. The only time I think that
you should wear dresses in winter is if you really are going from door to door with a taxi in between, where you have minimal walking outdoors. That’s the only time I
would personally approve of wearing a dress in very harsh climates. Now lastly, what about tights? So, hosiery is a very important topic because I do not wanna see
any bare legs in winter. Number one, it kinda
goes against etiquette and it doesn’t look very elegant. Sophisticated high class
women, they wear tights, but the problem with tights is that it can easily look very cheap. Now, you have to wear tights that blends in with your skin perfectly. Don’t go for the tights that have a mismatch in color from
your own skin color. The ones that are like
too, too white or too dark. Go for the ones that really
blends in with your skin tone. I’m talking about the nude color now. Invest in the higher quality brands. They tend to be better from
my personal experience. I love Wolford, I love Falke, and also don’t do this horrible mistake of wearing your tights
with open toe sandals. I don’t know why girls do that, and especially when you
can see the seam. Oh my God, no. The worst is like when
the seam starts breaking and they keep wearing
that and I’m like No! You are not supposed to wear
sandals in winter at all, even if you’re going by taxi. Any open toed shoes are
only for spring, summer. Fall, winter according to
etiquette you wear closed shoes. The only thing that is acceptable is a peep toe shoe but everything else with an open toe is a big no go. Black tights is fine. You can wear them but I would definitely only wear them together with black shoes so that they kinda blend
in with each other, but make sure your black
tights also look expensive. You don’t wanna have the like
cheap H&M stuff because yes, you can see that it is from H&M. A trained eye can see. Now before I wrap up I
want you to also take the advantage of wearing colors. I know it’s tempting to wear black because it’s comfortable and because we get easily dirty during winter, but whenever you wear some
like natural colors like gray, beige, white, khaki and so on, it just makes you look more expensive and not everybody’s wearing those colors. Majority wear black. So you will be standing out and I think you should take opportunity of that. Like use that to your benefit. Especially if you’re
somebody who wants to have a little bit of attention
and all eyes on you. Now also, make use of accessorizing, especially during winter because we tend to go a little bit
more basic during winter and things tend to become
a little bit more boring, now is actually a good time to pull out all those accessories. Like I said, wear that
hat, wear that scarf. I don’t know. Do something that is a little bit more creative then what you
usually would have worn. When it comes to fabrics, I love cashmere. I love tweed during winter. I think that these two fabrics are probably my favorite because they are very warming and they always look very high end and everything that looks very high end, I like. Now that was it for me ladies. If you’re interested to enroll in my online finishing school, the address is Is there any fashion tips that you want to add that is more winter specific? Have you found any winter hacks that you would keep using
over and over again? Share it with us in the comments section. Subscribe if you still haven’t
subscribed to my channel and hit me a like if you enjoy this video. Now, enjoy the holiday
season and stay warm girls.


  1. Canadian perspective: invest in an inner down jacket. If your slim enough not to look like a stuffed sausage when you wear it under a long coat – it's a life saver. Thin marino wool or Gor Tex socks that fit in your "fancy" boots, unless you're taking your shoes off infront of others no one will know. You're welcome.

  2. When you live in Southern California you don’t wear cashmere and heavy winter clothing. Why not make a post for those of us who live in spring like weather year-round and how we can change from summer to winter.

  3. I too share your love of equestrian sports, attire, fashion, all of it! One of my aunt and uncle owned a few horses. When I and my siblings and cousins were little, they use to take us riding. I thought it was the greatest experience. My love of equestrian was born!😊 Great content and video.

  4. At first I was like, why is this in my recommendation? But hey, a little vanity doesn't hurt. Totally enjoyed watching 👍

  5. I just wanted to say that I love your videos. I’m using them as a guide to better myself as I upgrade my own lifestyle. I’m a business woman on the way to becoming a millionaire very soon and I want to project my financial success outwardly.

  6. I'm very dark skinned and I hate black clothes. I prefer navy blue over black and love how orange and red look great with blue. I'm a fifty year old Black woman and allthough I can't buy many of the items you suggested right off the tack, I don't mind purchasing them second hand. I'm looking forward to my son's making more money than I have as a teacher so that I can begin adding those hifh end items to my wardrobe. My late sister was a prominent member of our community and I did select a few elegant items from her clothes to add to mine. I have about 100 pieces to sort through and hope there are more trousers and dresses that I can fit. Thanks for sharing such great ideas.

  7. YES to turtlenecks! Always always. Personally my style is fairly conservative but still modern so I do much better in winter- but scarves, a platform boot that’s flattering to the ankle and thicker material or non ripped jeans , tailored trousers are my go to

  8. How to stay chic and elegant in a cold freezing country? How about, how to stay ALIVE in a freezing cold country???

  9. What's a better investment is not white but a caramel or tanish brownish color. You can pair it up with black, white, cream etc. All white is too blinding and get's dirtier easily but tan, beige or caramel would be the perfect color as well as black or gray. Good shoes/boots are important to make an outfit look expensive and all the in between pieces can be less expensive if the budget isn't there.

  10. Girl if I have to freeze my ass off in a flimsy pea coat in nyc to impress a man then he’s a shallow dbag. These coats will not keep a nyc warm you’ve got to wear a down or Canada goose

  11. Anna, Love your vids! Now could you do please something for us ladies over middle age? There is nothing out there that is inspirational. They are mostly ridiculous and depressing. Thank you!

  12. Hi Anna! I've been watching your videos lately and I find all of your tips very useful. I think you really help women become empowered by loving and embracing our femininity and becoming classy women. Love all your tips.

  13. So refreshing to see a video on dressing for winter from someone who actually experiences winter! Yes – winter is snow and ice and temperatures of -25C and colder! Yes – it means walking on icy and slushy sidewalks! And yes, it means dressing in lavish layers to stay warm and cozy! I had the most beautiful and refreshing walk to the train this morning wearing layers of navy with leopard and plaid accessories. There was snow on the ground and stars in the sky and it felt so good to breath the crisp, clean morning air. We are so blessed to have the full spectrum of seasons and the varied wardrobes to match. Love from Canada 🙂

  14. Can you please create a video on how to look elegant at work and post graduate classes? Especially if you could do one for each season.
    Thanks for this one! It was very helpful.

  15. Those scarves and hats are not actually going to keep you warm. They are just decoration. What is attractive in winter is actually being warm and comfortable. It looks very snuggly and men love it! They just want to hug you 🙂

  16. What about rain, here in UK it can be torrential. Just walking from door to car park can ruin everything especially hair :(( I have to either have a hooded waterproof coat or carry an umbrella all the time!

  17. Thank you so much for posting this. I was born in a warm country and not familiar on how to dress in cold weather. This helped me so much plan for my london trip!

  18. I love to wear red from December until March. It’s one of my favorite colors. Red looks amazing on gray cloudy days and looks good into the night. You look fabulous and I love your beautiful style. 💋 Oh, what do you think about rain boots?

  19. I love your videos!!! I love that you include photos of all women of different ethnicities!!! Keep up the fabulous work.

  20. I love the long sleeve midi-length dresses but I am only 5'4 and pretty petite. What is your advice on short girls wearing long dresses?

  21. Classiness is about confidence and kindness. The way you're judgmental about others fashion choices and value money as someone's worth (she is against modern feminism and teaches girls how to date a billionaire for example..) is not classy at all.

  22. THANK YOU! Where I'm located, it's frigid cold 6-7 months out of the year! I've wanted to look great during winter AND stay warm. Some months as you said, it's near impossible, but after the worst is over, your tips should help make this my best dressed season ever. ❤️ Looking forward to taking your course in the new year! ❤️

  23. I love your videos. My husband is a diplomat and you’ve helped me level up my game with all these bougie bishes. I also love your judge-y attitude and resting B face. Keep serving the looks babe!

  24. I have big books and short neck. Turtel neck s and scarfs do not make me look good. What else can I have in winter? Is V neck ok?

  25. I am a Muslim women who wear dresses most of the time and also the head scarf, I am super glad you did this video. Very helpful. Thank you!

  26. I love your top. I love coats. I’m so obsessed with them. Love it in camel. I like to combine my coat with the shoes… the turtle neck in navy Merino Wool.

  27. i love your videos and everything you say but none of this applies when you actually get to -25 degrees… all style goes out of the window and survival becomes what matters

  28. I love your videos it is all about taking care of one self and making the best of one self, having pride and respect for yourself which a lot of women do not have. I do not go out wanting to meet a rich man just a nice kind man who has a lovely personality. But I think that your videos really are very useful in being the best one can be and you show how self care is so very important. I am at present loosing weight and will take on your tips and adapt them if necessary to my lifestyle. I do not have much money at all but I agree with you in regards to shopping if you can afford two skirts from a cheaper shop why not buy one instead from a little bit more expensive shop that will last longer. I have bought skirts from the cheaper shops and they fall to pieces, in one wash one had gone into holes!! SO in the long run they turn out to be more expensive! Also if you go to a nice richer area and go to the second hand shops you can really get better quality clothes that have been worn once or twice or never!. I am slowly making the change to do this, just waiting till I get to my goal weight which will be a size uk 12 which is my happy size. I think we all should take care of ourselves as best we can. Be the best we can be. Inspirational videos please keep making them. 🌸😊

  29. How To Dress Class In Winter

    1. Expensive Looking Coat
    2. Coat of High Quality material
    3. Riding Boots
    4. Over Knee Boots w/out heels
    5. Turtle Necks ( cashmere)
    6. Chic Hats and Scarves
    7. Jumpsuits, Trousers, Suits
    8. Hosiery that blends in w/ your skin tone
    9. Layer in Monochrome
    10. Chic Hats and scarves
    11. Accessorizing
    12. Wearing Colors/ Natural Colors
    13. High end fabric such as cashmere and twig

  30. Thank you for watching! What are your favourite winter hacks to look classy? For more content on elegant fashion watch my other video 10 Ways To Look Expensive On A Budget:

  31. where do you buy your trousers/matching suits? Or an alternative that isn't crazy expensive, but still looks nice?

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