Not Sure What To Wear Over A Dress? Next Level Layering Tips You’ll Love

We often talk about how a 3rd layer can elevate your outfit and give you that intentional and chic “it” factor. And, in the cooler months, stylish layering is even more of a necessity. But expert layering takes some thought when it comes to flattering your shape and creating versatility in your wardrobe. Today we’re talking about what to wear over a dress and sharing several outfit ideas! With a few mindful tips and techniques, you can breathe new life into your favorite dresses across multiple seasons. There are many different pieces that look great over dresses… but there is a knack for choosing the right ones.

Choosing the right pieces for your wardrobe each season is extra simple when you first have the wardrobe basics. You can sign up here to receive your free wardrobe basics checklist AND other amazing style resources by subscribing to our newsletter.

What To Wear Over A Dress

What To Wear Over A Dress

What To Wear Over A Sleeveless Dress

Let’s start with layering over a sleeveless dress…it’s one of the easiest because there’s no added bulk at the shoulders and arms to worry about. This is one great way to extend the life of your summer dresses into the colder months too.

Cropped Military Jacket 

A cropped jacket layered over your sleeveless dress creates a defined waist. Erin’s wearing a textured boucle crop jacket by Me + Em over her LBD for added warmth and style. It’s structured but has a relaxed and edgy aesthetic. Since it’s on the heavier side, this jacket will look best layered over a knit, wool, or thick cotton. We wouldn’t suggest wearing it over lighter-weight materials like silk.

Retrofete Puff Sleeve Denim Jacket

Denim jackets really don’t need much introduction, but there are a few things to consider before layering one over your dress. In most cases, a cropped, fitted, or semi-fitted denim jacket will create waist-definition and more of an hourglass effect…especially one with a puff shoulder like the Retrofete jacket Erin’s wearing above. A longer or boxier denim jacket could end up making your overall shape less defined.

Reiss Longline Blazer

In the last image above, Erin’s wearing a longline blazer by Reiss to transition her summery white dress to fall. The lapels and strategic darts work together to slim your frame. Are you starting to notice a theme here? Adding a top layer with waist definition over your dress is key to ensuring you don’t get lost underneath the added fabric! This is especially the case for a flouncier dress…a straight-cut jacket layer will balance out your proportions more beautifully!

What To Wear Over A Mini Dress

What To Wear Over A Mini Dress

Oversized Cardigan

Talk about extending the life of your summer dresses, how cool is Erin’s slouchy, textured cardigan on the left? The oversized fit works in this example because the dress itself is body-skimming and lightweight. Paired with the tall white boots, the fuzzy cardigan is effortless and casual-chic. The long line of the cardigan elongates the leg and draws the eye down from head to toe. Such a simple but flattering tip!

Chic Trench Coat

An elegant trench coat is a classic piece to layer over your dress. And it’s super easy because when it comes to trenches and dress length anything goes! You can wear a trench that’s longer than your dress, the same length, or shorter than your dress. The signature waist belt can be tied in the front or looped in the back to create a waist.

Classic Leather Blazer

If you want to instantly add some cool factor to your dress, wear a leather blazer! In the look above, Erin is wearing an Alice + Olivia faux leather blazer over a simple LBD. A black leather blazer is super versatile and can be worn for all kinds of occasions. You can wear it to the office, out to dinner, buttoned-up, or draped over your shoulders. The leather says “edgy” while the silhouette says “sophisticated”. We just LOVE it! There are so many wearable neutral leather blazers you can try if you aren’t a fan of wearing black. A leather jacket is also a wonderful layering piece over your mini dresses! We’ll link a few of Erin’s favorites below.

STYLE TIP: Adding tights and booties will also instantly transform your summer LBD into a winter-friendly LBD. Wearing a dress in the winter is all about keeping warm and covered up, but not sacrificing your unique style. This post highlights some additional tips for wearing dresses in the cold weather.


What To Wear Over A Maxi Dress Layering tips

What To Wear Over A Maxi Dress

With maxi dresses, there can already be a lot of fabric, so you want to be sure your layering piece doesn’t swallow you whole or eliminate your shape altogether. In most cases, a cropped jacket or blazer is going to be the most flattering over your maxi dress. In addition to your 3rd layer, you can also wear a belt for added waist definition! Each of the pieces described below will also work if you’re wondering how to add a 3rd layer to style a slip dress in cooler months.

Cashmere Sweater

In the look above, Erin added a bright pink pop of color to her maxi dress with a cashmere cardigan. Cashmere is an excellent layering fabric because it’s super warm without adding any bulk. Plus, good quality cashmere will last season after season, so while it may be a bit more of an investment, it’s worth the price per wear. If your maxi dress has sleeves, make sure the cashmere sweater you choose has some roominess at the arms.

Classic Blazer

We can think of hundreds of reasons why a classic black blazer is a wardrobe staple every woman should have in her closet. So, naturally, another way to style it is with…your maxi dresses! Erin’s double-breasted Balmain blazer has a tailored cut, stunning gold buttons, and sharp shoulders. It has a fitted silhouette which balances out the flowy material of the dress. It is on the pricier side, but Erin says it’s one of her most worn investment pieces. You can find similarly fitted blazers for less, so we linked a few below.

Cropped Blazer

Worn with a maxi dress, a cropped blazer does all the heavy lifting for you. It naturally creates a break at the waist for instant waist definition…which also makes your lower half appear longer and leaner. If you want to wear a longer blazer with your maxi dress, you can always add a waist belt over or under the blazer to create that same cinched waist.

What To Wear Over A Sweater Dress

What To Wear Over A Sweater Dress

Sweater weather is coming and sweater dresses are a popular way to keep warm in the cooler temps.

Teddy Coat

In this first look, Erin’s wearing a super snuggly teddy coat over a mini sweater dress. This will keep you warm and toasty! Since teddy coats add some bulk, a sweater dress is perfect to wear underneath since they tend to be more fitted to the body.

If you’re curious about other ways to style a teddy coat this winter, Erin styles 7 outfit ideas in this post.

Classic Blazer

Proving a classic black blazer truly is a wardrobe staple, another way to style it is over a sweater dress. This will help you get a bit more mileage out of your sweater dress (and your black blazer!) if you want to transform it from office or daywear to dinner. Draping the blazer over your shoulder adds such an elegant and distinctive touch…like you own the room!

Trench Coat

This is the same trench coat featured in the mini dress looks, but here Erin styled it with a wrap-front sweater dress. I know sometimes we think of trench coats as rainy-day wear only. But that’s an easy mold to break! The streets of Paris are full of stylish women sporting their trench coats on the sunniest of days. A trench coat will pair beautifully with so many of your sweater dresses…mini, midi, and maxi.

What To Wear Over A Cocktail Dress & What To Wear Over Formal Dress

What To Wear Over A Cocktail Dress & What To Wear Over Formal Dress

One common question we get is what to wear over your wedding guest dress, cocktail, or formal dress. You don’t want to cover up your beautiful occasion dress with just any old outerwear.

Elevated Cardigan

This first cobalt blue monochromatic look scored so many views on Instagram when Erin first featured it last year. Let’s break down why it works with her mini cocktail dress. The cardigan is made of an elevated faux fur material that coordinates well with the satin dress. It’s in the same beautiful color as the dress, has beautiful gold button detailing, and the length is the exact same as the dress, which is such a chic look. This pairing is very unexpected, modern, cool, and sexy!

Capes & Wraps

You might remember the second look above that Erin wore to the Dior Fashion Show in Paris earlier this year. She paired a gorgeous Dior cape with her elegant Dior cocktail dress. A cape made from a satin, silk, or cashmere material will work beautifully with your cocktail and formal dresses. You can also wear a shawl or wrap in a tone that coordinates with your dress. The key to pulling off this look is making sure your cape or wrap looks intentional and not like an afterthought. Sticking with neutral colors or wraps in the same color family as your dress is a safe bet.

Faux Fur Coat

In the last look above, Erin’s wearing the same cobalt blue satin dress but this time paired with a standout fur faux wrap coat. This look is SO glamorous and special and will certainly help you stay warm. In the colder months, pairing a long or short faux fur jacket, fur shawl, or coat with your formal dresses will look regal. You definitely won’t get lost in the crowd…in a good way!

Are there any other styling tips you’d like us to tackle here on the blog? Please leave us a comment below!

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2 thoughts on “Not Sure What To Wear Over A Dress? Next Level Layering Tips You’ll Love

  1. Help! Winter is on its way. I need advice and tips on wearing tights/pantyhose with a dress. I have never been sure of when to wear opaque vs sheer black tights, when patterned tights are OK depending on the length and simplicity of the dress, and if it’s OK to wear sheer pantyhose. Thank you for addressing fashion for a 40plus audience.

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