
After curating my closet time and time again over the past few decades and spending hours putting together outfits, I feel I have a good idea of the core winter pieces that most people need. These pieces never go out of style and can be reworn year after year with various winter looks. They are the items you can pair with your fun colorful accessories and trendy fashion finds because they are the foundation of all your winter outfits. Here are the 10 pieces to invest in to have the best winter wardrobe.
10 Pieces To Invest In To Have the Best Winter Wardrobe
Tailored Wool Coat
A tailored wool coat may be a splurge at the beginning but you may not need to ever purchase one again. Opt for a basic style without a lot of accessories or details so that it will be timeless and look great for years to come. A chic simple wool coat will never go out of style. I would recommend going with either camel, black or gray since they are neutral tones that will go with most of your wardrobe. The length of the coat may depend on your height but a mid-length style is the safest and most versatile option in my opinion. This is a coat that you can dress up for a night out, wear to the office or throw on with leggings and sneakers for the weekend.
Classic Cashmere Sweater
There are so many options available for investing in a cashmere sweater so you can go as luxe or affordable as you prefer but it’s a necessary winter wardrobe staple to own. Choose a neckline that feels the most comfortable and stick with neutral tones again so that there is less limitations on styling it.
Structured Blazer
Whether it’s a statement piece with chic gold buttons or something more simple, a structured blazer is always a closet essential. Avoid a style that is too oversized or too cropped as they can look more trendy. A regular style that hits around the hips is the best option. Another feature I like to look for with my blazers are ones that dart in at the waist. I find it looks the most flattering and creates a nice shape.
Silky Button Down Blouse
When it comes to button down blouses, I find that silky styles that have a bit of drape to them look so much more polished and elevated. And if it has a bit of sheen to it even better. The sheen works for both casual and dressy outfits whereas a cotton or stiff poplin style blouse is not as versatile. Start first with a cream or white option before venturing into anything colorful.
Sturdy Everyday Handbag
Winter handbags are my favorite styles because I LOVE the look of a sturdy leather or suede bag. Avoid logos or overly trendy styles because they can quickly fall out of fashion after a few seasons. Either a tote bag or top handle bag is best for everyday and will work best with a variety of casual or professional outfits.
Elevated Belt
If you scroll back to my earlier outfits on the blog, I hardly ever wore belts. Not quite sure why but I was never really into them and felt they weren’t super necessary to wear. Fast forward to today and I wear a belt with almost every single outfit! LOL I find belts really do elevate an outfit and add some texture, color or interest to any look.
Boots
Boots are kind of a no brainer for winter but deciding on a particular style can be difficult. If I was helping someone style their own winter wardrobe, these are the exact types of boots I would recommend. A pointy toe neutral boot either in suede or leather with a stiletto heel. The heel can be a small kitten heel under 2 inches or something higher based on your preference. But the key is to keep it simple, sleek and minimal in design which will never go out of style and always look modern.
Sweater Midi Dress
I always gravitate towards a simple midi (or slightly maxi) style sweater dress each fall/winter. It feels classic and comfortable, easy to style with knee high boots or pumps. Often this style is easy to wear on it’s own, but also looks great styled with a leather jacket or statement vest. Many midi sweater dresses have a more fitted silhouette and if you want to keep things work appropriate, I always recommend going up a size or two to ensure it’s not too tight. I also typically wear shapewear underneath if the dress is fitted or in a light color.
Dark Wash Denim
I have more jeans that I would like to admit but the ones I reach for the most during the fall and winter is a dark wash non-distressed straight leg or wide leg fit. If you struggle with finding a length that works for you because you are on the shorter side, choose a cropped style which most of the time will come right to the ankle. Or the option that I have been doing for 10+ years is cutting a few inches off the bottom to get the length I want. I used to take them to be hemmed but if I’m being honest, the hem was never as good as the original and I ended up regretting my choice to do so. I prefer to just cut the bottoms of my jeans and let them fray a bit over time.
Ballet Flats
As a die hard heels lover, I’m surprised at my current intense love for ballet flats. But here we are. Maybe it is after all those years of wearing super high heels that I feel my feet have earned a rest. Either way, I am thrilled that ballet flats are trending heavily at the moment. There are so many chic options available and a style to fit everyone’s taste and budget. I personally like them worn with jeans or trousers when I don’t want to wear heels or don’t want to go the sneakers route for comfort. My first choice will always be a pointy toe because it never goes out of style and instantly looks chic. But a simple soft round toe ballet flat is always going to be timeless too.

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