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5 Easy Ways to Look Put Together This Winter

Building a Wardrobe
January 4, 2023

I think every season brings its set of challenges as far as fashion goes. In the spring we’re ready to wear all the lightweight pieces and pretty colors, but the chilly temperatures require us to cover those pretty new pieces with outerwear. In the summer we’re just trying not to sweat. Ha! And the weather is all over the place in the fall, requiring us to be really flexible. But as we settle into the cold days of winter we sometimes struggle to look polished and put together without sacrificing the warmth and coziness we naturally crave this time of year. So today I’m sharing 5 easy ways to look put together this winter…while still staying warm.

Today I’m using a mixture of photos from this year and previous years. So many if not most of the items I’m showing are no longer available. We’re focusing on style principles here rather than specific pieces of clothing. But if you have a question about something you see, just let me know in the comments section. Generally I’m linking you to the original posts where you can get additional information.

Winter Styling Tip #1 – Wear thin insulating layers close to the skin under your streetwear if needed.

How to Look Classy in Colored Pants this Winter
Hampshire ankle pants // pumps // clutch // blazer (more economical option 1 and option 2) // cashmere sweater no longer available (similar) // chain link necklace // small necklace (use code KAYHRMS for 15% off) // similar brooches // earrings (not shown here)

Of course you can’t see it in the photo above, but I’m actually wearing a thin, close-fitting camisole under my sweater. You don’t have to add a lot of bulk or heft to add significant warmth with an additional layer. The key is not bulk, but wearing the garment close to your skin. So you want to look for under layers that fit comfortably, not tight, but close to the body. And then you want to make sure you have the variety you need with the different necklines that will work under your sweaters or tops.

How to Feel Warm + Look Stylish at the Office
See the original post from 2020 HERE.

I even wore a form fitting camisole under the blouse and jacket in the photo above. I remember it was freezing cold the day we took those photos in early 2020.

Slenderizing Column of Black under a Caramel Colored Coat
See the original post for details.

If you’re wearing a long sleeve top or sweater like I did above, you can even wear a long sleeve, close fitting t-shirt underneath. And in the photo below I was wearing a camisole underneath and then I layered on a thin cardigan underneath my suit jacket. Thin layers work magic!

Winter Work Look Layered with Class
No longer available – See the original post.

I like to have several camisoles and several long sleeve layering tees in my drawers for really cold days. I’ve collected a variety of tanks, camis and t-shirts in the widget below. They’re also constructed from everything from wool (the warmest!) to polyester to modal (a natural fiber fabric with moisture wicking properties) to cotton blends, and they’re at a variety of price points.

Getting those base layers on and hidden beneath your streetwear gets you well on your way to looking put together this winter. So now you don’t have to overdo the outerwear or look so bundled up as you work, play or shop.

Winter Styling Tip #2 – Do wear warm fabrics and enjoy mixing textures in your outfit.

There’s a reason why we associate fabrics like wool and cashmere with winter: they keep you warm.

Donegal Tweed Pants
Cashmere Sweater // See the original post.

Actually many natural fiber fabrics do a great job of keeping you temperate, meaning they keep you warm when it’s cold outside and they keep you cooler when the temperatures are hot. Silk is actually another fabric that will keep you temperate.

Beautiful Silk Shirt for Holiday Performance Look
Silk Blouse // See the original post from 2019.

Plus, winter is such a great time to wear these rich, textured fabrics. I suggest you aim to put together outfits that include multiple textures to create the most visually appealing combinations. Mixing textures will help you look more put together, like you’ve put a little thought into your attire.

How to Stretch Your Wardrobe
See the original post.

The good thing about wearing inherently temperate fabrics is that they don’t have to be very thick to do their magic. Even a relatively thin cashmere or wool sweater, for instance, will keep you as warm as a chunky knit sweater will, if not warmer.

See the original post.

But if you have sensitivities to wool or cashmere, you’ll simply want to look for those chunky and/or tightly woven sweaters that promise to provide the warmth you need and the style you want.

What I Wore for an Autumn Day Trip
Fair Isle Sweater (does contain 7% wool) // See the original post.

Of course, don’t forget to add other seasonal fabrics to your outfit lineups, too. Winter is a great time to add flannel to your outfits. Keep the look chic by balancing out any plaid or print flannel with neutral solids in the rest of your outfit.

Casual Outfit for a Festive Outing
vintage straight leg jeans // fitted flannel shirt in pink plaid // western booties // zip-up quilted vest // similar earrings // See the original post.

And another seasonal fabric I enjoy adding to my winter outfits is corduroy. A lot of stores that sell corduroy are selling out fast about now. But if you have cords in your closet, pull them out and wear them through the rest of winter. They’re a great casual option to choose instead of jeans.

Winter Styling Tip #3 – Wear stylish and warm hosiery on your feet.

Things are not always what they appear. Frequently when I’m wearing pumps or other shoes without socks in the winter…I’m actually wearing socks! You can find great socks (that stay in place!) to wear under ballet flats, pumps, loafers, etc., and provide at least that thin layer of warmth close to your tootsies. Every little bit helps!

Look classy in colored pants this winter
Hampshire ankle pants // pumps // clutch // blazer (more economical option 1 and option 2) // cashmere sweater no longer available (similar) // chain link necklace // small necklace (use code KAYHRMS for 15% off) // similar brooches // earrings  // ultra low rise socks

You can even wear the Sheec Socks ultra low rise socks with the pumps shown above. I’ve got more options for ankle and foot-baring socks in the shopping widget below. But if you want to cover your ankles and wear more substantial socks with your loafers or Oxfords, you absolutely can do that and still look put together this winter.

Wear White Socks
See the original post, “How to Wear Socks Stylishly This Winter.”

My theory is – and lots of stylists agree – that if your socks are going to show as you walk and stand, you should wear them as accessories to your outfit. So don’t try to make them blend in. Wear socks that will add a punch of color or texture to your ensemble intentionally, decisively.

What I Wore to My Hair Appointment
Socks // Shop the look HERE.

On the other hand, if your socks will generally be hidden under boots or your pants leg but will only occasionally peek out as you sit down, wear them as undergarments. So then you do want to wear socks that blend in with your pants or boots. I especially like to wear my J.Crew cashmere blend socks. And they happen to be on sale right now.

Of course if you’re wearing a dress or skirt you can wear hosiery or tights to keep a little warmer. With the faux leather dress below I’m wearing the Spanx micro-fishnet midthigh shaping tights in nude. No, they don’t provide a LOT of warmth, but they do help some. And they look great! You could wear thicker hose, of course, but I’d stick with some that are very sheer in color and nude or the color of your boots, in this case.

Brown Leather Dress and Knee High Boots
faux leather dress // brown suede boots // textured wool blend coat in washed cranberry // earrings // watch (use code KAYHRMS for 15% off, stack on savings) // clutch no longer available // necklace (use code KAYHRMS for 15% off) // Spanx micro-fishnet midthigh shaping tights in nude

If you’re wearing tights, I always suggest you try to match the color of your shoes or boots to create a continuous leg line. Otherwise match your skirt.

black puffer vest
See the original post.

I found lots of great no-show socks of all types, wool socks and others in the shopping widget below. I also have some hosiery and tights in the mix, but I couldn’t get the J.Jill offerings to load, so let me tell you about them. I love J.Jill’s opaque tights and wear them every winter. But this year they also have fleece lined tights. And if you’re just looking for that underlayer, but not necessarily socks, check out J.Jill’s footless tights and their fleece lined footless tights.

Winter Styling Tip #4 – Add boots!

If your climate demands it, you can wear boots or booties with absolutely everything during the winter.

Dress on the Move
See the original post.

I love wearing boots with a dress.

A-line dress
A-line dress // cotton blend camisole // pearl and rhinestone pendant necklace // boots // See the original post.

Right now a western vibe is in, but you can still wear your more traditional looking knee high boots and look very on trend.

Are Knee High Boots Out of Style?
See the original post.

And you can still wear knee high boots with jeans, too. Just wear either skinny jeans or jeggings or very slim fitting straight leg jeans so they fit nicely into your boots. (That said, the blousy look is actually “in” with riding boots right now. The edgier, hipper crowd is wearing their fuller leg jeans stuffed inside tall boots. Go figure!)

Why I'm Keeping My Skinny Jeans
See the original post.

But of course booties are the perfect option for most jeans and pants this time of year. If you’ll be in inclement weather, make sure you have boots or booties with lug soles and that are water resistant or waterproof.

Similar booties // See the original post.

I like to wear my booties in the same intensity level as my pants. So they don’t have to be exactly the same color as your pants, but if they are in the same level of intensity (say dark brown with dark denim or soft sand with light wash denim) then the line of your leg will appear more uninterrupted and visually pleasing.

What I Wore for an Autumn Day Out
See the original post.

If you have a pair of lighter colored booties and a pair of darker booties in your closet, you should have no trouble creating outfits that look really put together for winter.

Red and Brown for Thanksgiving
Shop the look here.

Winter Styling Tip #5 – Wear coats and accessories that add value to your outfit.

In the winter your outerwear is an important part of your outfit. This is the way many people you encounter in any given day will see you first. So it’s important to have coats and winter accessories that add value to your outfit rather than detract from it.

Shop the look HERE.

I think it’s smart to have at least one coat in a neutral that you enjoy wearing. You could opt for camel, black, grey or even navy. If you wonder which will serve you best, consider trying a coat in the same tone as your hair color. For instance, women with grey or silver hair will look great in grey coats and women with blond hair frequently look great in camel or beige coats.

Winter Classics with a Column of Black
See the original post.

But I also think it’s smart to have a colorful coat in your closet for winter. I especially like to wear a colored coat over an otherwise neutral outfit.

Faux Leather Dress & Red Wool Blend Coat
coat // See the full post here.
Red Coat looks great over Neutrals
See the original post.

But another great outfit combination with a colored coat is to wear it with the same color top or dress. Oh so chic!

Blue Coat with Blue Sweater
See the original post.

Even if you need a warm, cozy puffer coat or parka, you can choose one that adds value to your outfits. Just keep this principle in mind as you shop for a coat.

Introducing Dongli Cashmere with a Casual Outfit
See the original post.
Puffer Coat

And then complete your outerwear with a pretty scarf and maybe hat and gloves.

See the original post.

I hope these five tips help you feel more confident as you put together outfits this winter. Yes, we have to bundle up sometimes, but that doesn’t mean we have to lose our style. With some smart layering, good fabric choices, the right options on your feet and a pretty coat you absolutely can look smart and put together this winter.

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Blessed for My Day

I find it interesting that when Adam and Eve sinned they became ashamed of their nakedness and created coverings. But when God discovered their shame, He made for them “garments” and “clothed” them. Adam and Eve tried to hide their shame. God took action to restore their dignity. Of course, He did much more than just clothe them with garments made of animal skins. He also set into motion a plan He had devised before the foundation of the earth to redeem them through the blood of Jesus, the Messiah.

Why do I feel passionate about helping women look their best? Among other reasons, because I have known so many women who hide behind their clothes. Whether they don’t feel good about their bodies and hide behind oversized clothes or they feel unworthy and dress to be invisible, many women are trying to be as inconspicuous as possible through their clothing. But I believe that God has paid the ultimate price to redeem us out of our bondage and shame. We are called to be lights in this world, and we need to show up beautifully and graciously so we can glorify our Savior.

Then the eyes of both were opened, and they knew that they were naked. And they sewed fig leaves together and made themselves loincloths. ~ Genesis 3:7

And the Lord God made for Adam and for his wife garments of skins and clothed them. ~ Genesis 3:21

xoxo, Kay
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9 thoughts on “5 Easy Ways to Look Put Together This Winter

  1. Question about your Veronica Beard Miller jacket… that’s one of my faves that you have, but I wondered how it ran size-wise? They have it on sale in size 12! I like to be able to button a jacket, so I have sometimes worn a 12 albeit 10’s also work. How do you assess the sizing?

    1. Hi Kathy. It’s a great jacket. And I think there’s a little wiggle room in the sizing. I have my usual size 8. But I tried the 10 and it worked well too. So I realize it is a final sale item but if 12s have worked for you before it definitely could in this jacket too. And a tailor might could help you out with sleeve length and such.

  2. This is a great blog to show us how to dress warm in the winter, especially since my area in MInnesota is deep in snow and
    cold weather. Love your tips on the tights and socks, cashmere and light tops under other items for warmth. Sometime we forget
    to add these items. Great BFMD. Loved the reference that God made us to be called lights in this world so we can can show up to
    be beutuful and graciously so we can glorify our Savior. Never thought of us as his people in this way.

  3. I love all your looks, Kay. While I don’t need outfits for COLD weather, I do purchase bits and pieces to supplement my winter wardrobe for the occasional really cold spells. Happy anniversary and will you show us what you wore to dinner?

  4. Absolutely LOVE your look with the red/wh/black plaid skirt with black on top, black tights and booties! I live in Wisconsin so skirts are out of the question for me. I wear long underwear all winter (not the same pair of course! Ha!) Also I wear only turtlenecks in the winter because my neck and shoulders are sensitive to cold. Thank you for all your stay-warm advice.

  5. Hi Kay, I have long admired your Ann Taylor washed cranberry coat shown in this post over the leather dress. I have been searching for a winter coat with some color and love that this one is a softer color. Just placed my order for the petite small and am hoping this one works. Thanks for all you do. I enjoy your posts.

  6. This was great! I loved the different styles to look good and keep warm thru the winter. I had to laugh about the camisole years ago I was helping a friend out who owned a clothing store and one of the older woman who also worked there told me that wearing a cami is a great way to stay warm during the winter-time and to this day I still remember that and have multiple different color camis.