How to Wear A Shirt Dress in the Winter

Shirt dresses are one of my favorite types of dresses. I love the versatility and how you can wear them for so many occasions. Put it on and you instantly have a chic outfit. Shirt dresses are definitely a classic item so they’ve never gone out of style. But lately they have become more popular then ever and are far beyond the preppy piece you may think of them as. Traditionally we all think of them as something for the warm weather months, but with the right styling you can wear them in the Winter as well. And who doesn’t love getting more versatility out of their wardrobe?

How to Wear a Shirt Dress in the Winter

Not that you need it but I gave everyone permission to have several shirt dresses in their wardrobe. They are tons of ways to wear a shirt dress. I’ve put together a bunch of outfit ideas below on how to wear a shirt dress in the Winter.

Add Faux Fur for a Fancy Night Out

Faux fur is a Winter staple. A faux fur jacket or vest elevates a shirt dress to make it appropriate for evening. Add fancy accessories and heels to complete the look. I love the crop length of the faux fur jacket. It plays with the proportions of this outfit when paired with a maxi length shirt dress. If you worry that a maxi will be an overwhelming look, keep the dress in a solid color and wear a pointy toe heel!

Ring Set // Lipstick // Faux Fur Coat // Maxi Shirt Dress // Tote // Bow Earrings // Jimmy Choo Pumps

Add Tights to a Belted Shirt Dress for the Office

Tights are an easy and obvious way to get a shirt dress ready for Winter. They not only provide warmth but the dark color makes the outfit wintery as well. Black tights will go with most shirt dresses but don’t be afraid to try grey, navy or brown.

Belted Shirt Dress // Layered Necklace // Tights // Booties // Tote Bag

Add a Knee-Hight Stiletto Boot for Date Night

Don’t think a shirt dress can work for date night? I beg to differ. Start with a shirt dress in a dark color, bonus points if its in a silky or chiffon fabric. This one also gathers at the waist which accentuates or creates an hour glass figure. To add a little sex appeal, you can wear a lacy bra and un button to the point that it peaks thru. Knee high boots work like a pair of tights to provide coverage and keep you warm but allow you to show a little slight of skin. The stiletto heel is always a sexy option for evening.

Hoop Earrings // Silk Tie Dress // Clutch Bag // Knee High Boots // Lady Coat

Add a Leather Jacket

Leather jackets have to be mentioned anytime I talk about Fall and Winter style. I included them in my Winter Capsule Wardrobe post because they are that essential. A leather jacket can balance the preppiness of a shirt dress while also making you seasonably appropriate.

Keep it Casual for the Weekend

I love to be comfortable but still cute on the weekend. For a quick outfit, layer a sweater over a shirt dress and add tennis shoes. Any of the cable knit or crew neck sweaters you already have in your closet are perfect! You’ll be warm but comfortable and the layers make your outfit chic! I love to keep the rest of the outfit simple with some simple studs and a crossbody bag.

Cable Knit Sweater // Shirt Dress // Stud Earrings // Tennis Shoes // Cross-body Bags

Layer a Long Cardigan on Top

On days that you don’t quite need a coat, grab a long cardigan. Layer it over any shirt dress, just make sure the arms of the dress fit well under the cardigan. You want to prevent bunching. If your shirt dress has cuffs you can have them peek out. A long cardigan can go dressy or casual, depending on how you style the rest of the outfit. This outfit below could work for a business casual outfit if you switch the boots to heels.

Knotted Cross body // Layered Necklace // Shirt Dress // Duster Cardigan

Heeled Chelsea Boots // Chain Bracelet // Knot Bracelet

Add a Sweater Vest Dress

Another great shirt dress outfit idea is to layer a dress over a dress! A sweater vest dress or sweater dress can go over a shirt dress to add layers to the look. Layers always make an outfit more interesting. Pull the cuffs of the shirt dress to peek out from the sweater sleeves. A shirt dress can also add length to the sweater dress if you need it!

Knot Headband // Sweater Vest Dress // Shirt Dress // Tights

Heeled Boots // Cross-body bags

Keep Your Outfit All Black

Keeping a look monochromatic is one of my go to’s when I need outfit inspiration. The easiest color for monochromatic outfits is black and an all black outfit will always work for the Winter! To keep the outfit from being one note, use items with different textures. For the outfit below the silky shirt dress is paired with a chenille sweater and leather accessories.

Hoop Earrings // Maxi Shirt Dress // Chenille Sweater // Quilted Crossbody // Stiletto Booties

Add a Denim Jacket

Like a leather jacket, a denim jacket and shirt dress is another outfit idea. They typically lend themselves to a casual outfit and work well for the weekends. Whether your shirt dress is long or short sleeved, denim adds a great layer for winter. If you need more for the cold weather, most denim jackets can fit under a heavier wool jacket too.

Pair a Shirt Dress with Your Favorite Sweater

A common way to layer a business casual outfit is to put a v neck sweater over a collared shirt, this works the same with a shirt dress. The collar can peek thru the neck of the sweater. It also breaks up the up the solid color of the dress.

V-Neck Sweater // Cross-Body Bag // Pocket Shirt Dress // Tennis Shoes

Add a Blazer

Blazers

Blazer // Tie Shirt-Dress // Chain Necklace // Block-Heeled Pumps // Tote Bag

Layer a Sweater Vest on Top

Of course I’m gong to recommend my favorite of the moment trend, a Sweater Vest . In this post I have tips and trick on how to style this trend and lots of outfit ideas!

Blazer Coat // Sweater Vest // Shirt Dress // Banana Heel Sandals // Belt bag

Pair a Shirtdress with a Sweatshirt

Yes, even a sweatshirt can work with a shirt dress! To look put together while still comfy, pick a sweatshirt that isn’t too oversized and let the collar of the dress peek thru. Too oversized can make the outfit look sloppy. You don’t need many accessories either. For the look below I kept it to a tote and leather sneakers!

Pocket Shirt Dress // Sweatshirt // Leather Sneakers // Tote Bag

Layer A Long Sleeved T-Shirt Underneath

A fitted long sleeve shirt is a classic layering piece. In this post, I discuss the best layering pieces and how to incorporate them into your wardrobe. Long sleeves provide the coverage and warmth needed to make a shirt dress ready for winter. This is an especially great idea for short sleeve dresses. It also gives another opportunity to add another color or print to the outfit. You can take this outfit idea as a way to mix prints. A striped shirt dress would look really cute with a leopard or polka dot long sleeved shirt.

Pocket Shirt Dress // Long-Sleeved Shirt // Loafers // Oversized Shopper Bag

More Shirt Dresses

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