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How to Build a Wardrobe: Winter Work Style with 15 Outfit Options

How to Build a Wardrobe: Winter Work Style with 15 Outfit Options

It can be overwhelming to try to build a cohesive wardrobe. We may buy pieces here and there, but after a while it feels like we have a million articles of clothing, but nothing that actually goes together. Here are 17 essential fall and winter work articles that create a cohesive wardrobe on their own, but also gives you options to mix in additional fun tops and sweaters. You may even find that you have some of these pieces in your closet already!

How to Build a Fall or Winter Work Wardrobe

Blazers: I suggest you find a couple of really great fitting blazers in classic colors like camel, gray, or navy. Black would also be a nice addition, but I find that it a bit more harsh than the other neutrals, and it can be difficult to match the right tone of black slacks.

Dresses: The two you need are a basic long-sleeved black dress and a sleeveless sheath dress. The options are pretty endless with these two basics. You can always add a pair of tights when it becomes really cold.

Sweaters: I suggest having a couple basic crewneck sweaters—the neckline is appropriate for work and looks beautiful with a statement necklace or a collared shirt peaking out. I have found navy and black sweaters to be the most handy, but I also like having a bright color like a persimmon red to spice things up when the days are particularly gray. You also can never go wrong with a classic black and white striped sweater. Just make sure the stripes aren’t too thick or it will look like something the Hamburglar would wear.

White Button Down: You need one—trust me. You will see that the options are endless below.

Slacks: You need at least one pair of black slacks and a pair of navy. These will be the real workhorses of your wardrobe. I also like having a pair of maroon pants during the fall and winter. It’s close enough to a neutral that they will go with way more pieces than you would think, and they are a fun change from black and navy

Black Jeans: If you work in an environment where you can get away with black jeans at work, do it. They still look polished, and some days you just really want to wear jeans to work.

Shoes: For the fall and winter, at the very least you need a pair of saddle tan riding boots, a pair of gray heeled booties, and a pair of black heels or flats. For even more options, it doesn’t hurt to add in a fun pair of leopard loafers or red flats.

Accessories: For the sake of completing the look, I’ve suggest two potential statement necklaces: a tortoise chain necklace and a pearl statement necklace. However, these looks will work with any necklace or jewelry you love.

Now here are 15 outfit combinations using only the staple pieces outlined above.

How to Build a Fall or Winter Work Wardrobe

Outfit 1: Navy, maroon, and gray are beautiful together. Pop a white collared shirt beneath the sweater and allow the hem to hang below the sweater.

How to Build a Fall or Winter Work Wardrobe

Outfit 2: I always feel polished when I wear this outfit combination. Wear the button down beneath the sheath dress and pair with the riding boots. On really cold days, wear a pair of tights: black or navy would work.

How to Build a Fall or Winter Work Wardrobe

Outfit 3: Or you could simply pop a blazer over the sheath dress. You could still do the riding boots with this if you don’t want to wear the heels.

How to Build a Fall or Winter Work Wardrobe

Outfit 4: This combination feels French chic to me—so easy and comfortable to wear.

How to Build a Fall or Winter Work Wardrobe

Outfit 5: The red or leopard shoe is what makes this outfit.

How to Build a Fall or Winter Work Wardrobe

Outfit 6: This outfit would be adorable with any of these shoes. Just decide which seem most appealing or comfortable to you that morning.

How to Build a Fall or Winter Work Wardrobe

Outfit 7: Here is an example of how black jeans would be acceptable for work. This would also be a great outfit for the weekend. Two birds, one stone.

How to Build a Fall or Winter Work Wardrobe

Outfit 8: Another great color combination: camel, navy, and maroon. The riding boots or leopard shoes would look great with this.

How to Build a Fall or Winter Work Wardrobe

Outfit 9: Easy and comfortable.

How to Build a Fall or Winter Work Wardrobe

Outfit 10: The gray booties would be cute with the black dress. If it’s particularly cold, you could pair with black tights.

How to Build a Fall or Winter Work Wardrobe

Outfit 11: I LOVE the combination of color and pattern in this outfit! The persimmon red with the leopard and tortoise necklace—so stylish.

How to Build a Fall or Winter Work Wardrobe

Outfit 12: Here is another similar version, but with black jeans, a white button down beneath, and riding boots.

How to Build a Fall or Winter Work Wardrobe

Outfit 13: The striped sweater would look great paired with the maroon pants, gray blazer, and the gray booties. But if you want to dress it up even more, the black heels would also pair nicely.

How to Build a Fall or Winter Work Wardrobe

Outfit 14: Similar version, but with black jeans, a camel jacket, and riding boots. I love combining black with camel or saddle tan—so stylish. Here is another tip: if you’re going to wear riding boots with pants, try to do it with black jeans or a pair of slacks that fit more like leggings. If you wear riding boots with regular dress pants, it bunches in weird places. Just trust me on this one.

How to Build a Fall or Winter Work Wardrobe

Outfit 15: One more combination similar to one shown before, but with the gray blazer.


I hope this gives you some ideas for what may already be in your closet, as well as a direction for what you can invest in for the future. These are pieces that will work for years to come—in fact, these are staples that I have had for years.

In the next couple of posts I plan to show you some fun tops and sweaters you can work into this basic equation, as well as ideas for how you can carry some of these pieces over into the weekend.

Thank you so much for stopping in, friends! If this is something that would help someone you know, please feel free to share the link with them on social media or Pinterest. My hope is this will become your little wardrobe toolbox.

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