Classy Tailored Vest Outfit Ideas

Classy tailored vests are all the rage right now, and for good reason! They have become a timeless wardrobe staple that will elevate any outfit. Regardless of the season, tailored vests can be seamlessly incorporated into your look. In the summertime, pair them with tailored shorts for a chic outfit idea. For winter, layer your vest over trousers and complete the look with a warm coat. They can also be styled in a variety of ways for different occasions. For a romantic date night, opt for a skirt and let the vest add a touch of sophistication. If you’re aiming for a casual yet chic daily look, pair the vest with jeans. And for a classy workwear ensemble, wear it with trousers and a blazer. The options are endless when it comes to styling classy tailored vests, which is why I am sharing some of my favorite options below.

Also, for more classy style inspiration, be sure to check out these posts as well: Classy Black and White Swimsuit Outfits, All White Outfits for Summer, and my Summer Capsule Wardrobe.

Classy Tailored Vest Outfit Ideas

Classy Tailored Vest Outfit Ideas

Sharing a variety of classy tailored vest outfit ideas to inspire your wardrobe for any occasion. Whether it be casual or workwear or anything in between, I’ve got you covered.

Monochrome Tailored Vest + Trousers Outfit

Classy Tailored Vest Outfit Ideas

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A monochrome white tailored vest and trousers outfit is one of my go-to choices for a classy and timeless look. Monochrome white is chic and will never go out of style. Additionally, this look is perfect for a variety of sophisticated occasions. For example, add heels and a blazer and it is perfect for a workwear look.

Tailored Vest + Jeans Outfit

Classy Tailored Vest Outfit Ideas

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Incorporating a tailored vest into your everyday outfits will not only instantly elevates your look, but will also make getting dressed easier. This is because they are so easy to style for many occasions. For a casual daily look, wear your tailored vest with casual jeans. Then, add neutral sandals and a coordinating bag. This outfit is perfect for anything from brunch with friends to simply exploring the city in style.

Monochrome Tailored Vest + White Shorts Outfit

Vest Outfit with shorts

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A white tailored vest can create a gorgeous monochrome look when paired with white shorts. For a chic date night outfit, style your white tailored vest with a white shorts. Then, complete the look with white heels and a matching bag. To easily transform this look into a workwear outfit, add a blazer for a polished and professional vibe.

What to Wear with a Tailored Vest


Pair your tailored vest with tailored trousers or a pencil skirt for a sophisticated office look. Then, add a crisp blazer complete the outfit with pumps or loafers. For accessories, make sure you go subtle. Add a neutral handbag or simple gold jewelry to complete the look.

Date Night:

For a chic and stylish date night look, pair your tailored vest with a midi skirt in a neutral color. Go for a slip skirt and heels for a more elevated look, or a denim skirt and sandals for a more casual vibe. If you want to add an elegant touch, try going for a monochrome color scheme, such as white or black.


To achieve a casual yet chic look, combine your tailored vest with a pair of jeans or denim shorts. Then, add a basic t-shirt or a blouse, and accessorize with sneakers or flats for a comfortable and stylish outfit perfect for running errands or meeting friends.

Lunch Date:

For a casual lunch date, wear your tailored vest with a flowy midi skirt or tailored shorts. Go for a lightweight fabric to keep it relaxed and comfortable. Then, pair your outfit with sandals or wedges and accessorize with a crossbody bag or a straw tote for a laid back yet put together vibe.


To dress up for a formal event, layer your tailored vest over a dress or a pair of tailored trousers. Stick to a monochrome or complementary color palette because that will keep the look feeling sophisticated. Add elegant accessories, such as high heels, statement earrings, and a clutch to complete the outfit.

Shop My Favorite Tailored Vests

Sharing some of my all time favorite tailored vests for every occasion. Simply click on each image below to shop.

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Also, be sure to check out my most recent posts for more style inspiration!

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As always, thank you so much for stopping by today, I truly appreciate all of you! xx, Amanda


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