how to wear a sweater over a dress shirt

How To Wear a Sweater Over a Dress Shirt in a Chic and Classic Way

Please note that this post may contain affiliate links and any sales made through such links will reward us a small commission – at no extra cost for you.

A sweater over a dress shirt- this is what prepster fashion dreams are made of. And though it may sound simple (don’t you just, idk, put a sweater over it?), there are a few key things to keep in mind on how to wear a sweater over a dress shirt so you can look classic and chic!

sweater | jeans | loafers

Even if you don’t resonate with having a preppy style, wearing a sweater under a dress shirt or button-down is a great way to achieve a chic casual look. After all, you can’t go wrong by pairing two classic items with each other! The more the merrier.

Choose the right dress shirt

We’ve got to start with the basics. You want to choose the right kind of shirt to go underneath for a successful look!

Generally, you’d want a slimmer-fitting shirt so you don’t look too lumpy under your sweater- adding unnecessary bulk.

And so you don’t feel like you’re drowning in material, try to choose a thinner dress shirt if you can.

Opt for a long sleeve shirt instead of a short sleeve shirt. You want the arm cuff to peek out under the sleeves for the full effect, plus, a short sleeve collared shirt under a sweater may just look a little lumpy and odd.

It’s personal preference whether you want to leave the sleeves long or cuffed. Having them buttoned can come across as more polished, and cuffing and scrunching the sleeves can look more fun and undone. Neither are wrong!

For fewer layers but the same look, you could also choose a sleeveless dress shirt instead.

Choose a dress shirt in neutral tones for a timeless look. White is a classic color, but you could try dark colors as well, such as black or navy.

Dress shirt tucked or untucked? You can go either way with this.

If your dress shirt is long enough to hang past your sweater a good amount, then feel free to leave it untucked.

If your shirt is standard size, then keep it tucked. It should look intentional- not like you have a couple of flaps poking out!

This is a great outfit idea for the colder months. It’s the perfect way to provide warmth and layers while still looking chic.

Choose the right sweater

A v-neck sweater or crewneck sweater is the best type of sweater for this look! And a long sweater sleeve is a better pick over a short sleeve one.

If you wear a v-neck sweater, then keep your shirt collar relaxed and the top buttons undone. You don’t want to look like a stuffy librarian. (Sorry, librarians, for this bad stereotype.)

A chunky sweater can work as well. A fair isle sweater is quirky chic for the winter months and can keep you warm on cold days.

Choose solid colors for your sweater in order to look classic and chic. If you wanted to add a subtle print, a great way to do that is to choose a dress shirt with simple stripes.

But when it comes to the sweater, simple and neutral colors are best, as it’s one of the best ways to make anything look classic and chic!

Many women love these $50 cashmere crewneck sweaters from Quince. Great value for the price!

Alternatively, you could always wear a sweater vest over a dress shirt for a similar look.

Though you have a lot of options, a turtleneck sweater is not the best fit for this look. Though you could always wear a dress shirt over it if you’re feeling adventurous.

To take the guesswork out of it, you can always purchase a “ready-made” layered shirt with the two pieces combined too!

How to style the rest of your look

It can be worn in many different ways, but an easy way to wear this dress shirt sweater combo is to pair it with jeans.

If you’re headed to formal events, pair with black dress pants. A sweater and dress shirt combo can also be worn with skirts too. Great for the office, church, or wherever else you want to look a bit more dressed up.

When it comes to shoes, the sky is the limit. Whether it’s loafers, ankle boots, or flats, you can’t go wrong. All of these pair well with the classic pieces.

Did you know that you can layer on top of this look too? Whether it’s a leather jacket or a blazer, you can easily add an even extra layer to this outfit, adding style and warmth for the cold weather.

Though this combo is usually thought of as part of a school uniform for boarding school (you’re just missing a tennis skirt) or for something that only men wear, now you can see that with just a few styling tips, you can wear this look in a chic, classic, and feminine way!

To get started: pair your favorite long sleeve crew neck sweater with a long-sleeve white button-down, jeans, and loafers.

Now that you’ve mastered this outfit, it’s time to master wearing a camel coat. For the best classic outfit ideas using a camel coat, keep reading!

Up Next: How To Wear a Camel Coat | The Best Classic Outfit Ideas

how to wear a sweater over a dress shirt


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.