Dressy Casual

The daunting task: dressing up while dressing down. How to do dressy casual?

The way I see it, the outfit revolves around the body, aka the premiere layer of clothing. This could be pants and a shirt, a skirt and a shirt, or a dress. If the premiere layer is on the casual side, use the secondary layer to add pizazz (accessories, outerwear, shoes, tights). And, of course, if the premiere layer is on the dressy-side, dress it down with a more casual secondary layer. Does that make sense? No? Let me show you.

Example 1: Casual dress with blazer and heels

Casual Dress:

Sparkle & Fade Knit Printed Circle Dress

With a pop of color:

UO Opaque Tight

High heels:

Faux Suede Mary Jane Pumps

And a nice blazer:

Tiered Blazer

When looking at a black/white dress, I always recommend a pop of color. This could be in the accessories, shoes, tights, or jacket.

Here’s another example in this category:

Casual Dress:

Sparkle & Fade Knit Colorblock Circle Dress (pink)

Dressy flats:

Gathered Front Flats

A super fancy blazer:

Sparkle & Fade Embroidered Leaves Blazer 

And a nice hair accessory:

Nature Halo Headwrap

Using the blazer from above, here’s an example of casual premiere with something other than a dress.

The dressy blazer again:

Sparkle & Fade Embroidered Leaves Blazer

With a nice top:

Pins and Needles Peplum Tank Top

And colorful pants (the deeper the color, the fancier it is):

BDG High-Rise Seamed Cigarette Jean – Red

And classy heels:

Faux Suede Mary Jane Pumps

And a nice headwrap:

Daisy Goddess Chain Headwrap

Example 2: Dressy dress with casual secondary layer

Take this fancy dress:

Pins and Needles Tulle Overlay Halter Dress

One way to dress this down is adding a bomber jacket, like this one:

Leatherette Bomber Jacket

And you could add any range of shoes, now that the jacket has sufficiently dressed down the outfit, but I love this dress with short cowboy boots like these:

Short Cowboy Boots

Here’s another example:

Take this gorgeous dress:

Burnout Rose Dress

With this informal cardigan:

Draped Knit Cardigan

And adorable booties:

Peep Toe Wedge Booties


This is a pretty short post, but I hope it helps!
Just remember that you always wear a premiere layer of clothing (skirt, pants, top, dress) and a secondary layer (jacket, accessories, shoes). The best way to be dressy casual is to make one layer casual and the other dressy. The best of both worlds! (As my idol Hannah Montana would say.)