My focus for the posts this week originally came from a reader request for casual Friday wear and some cool weekend looks. Mid-week through our largest conference of the year and having donned business formal attire everyday for the last four (yes that includes Saturday and Sunday), I couldn’t agree with that need more. I too am longing for some casual! I took her request one step further … to showcase how the pieces you own can work harder by mixing both casual and formal. This concept also works wonders for traveling and packing. #tinysuitcaseproblems
The original request was specifically for looks with chinos and pants like my newest obsession … the cropped flare … but I also wanted to showcase similar wearability with skirts.

So this week you will see posts to help you create multiple looks from the same pieces. These will be looks you can wear to work, brunch with the girls and even a play date or two. Today’s post, 3 Shirts + 3 Skirts = 8 Looks, clearly focuses on the skirts while Thursday’s post will focus on multitasking with pants.

The pieces styled in this post were not chosen specifically for this post, rather they were items I recently acquired and was trying to decide whether to keep or return. My criteria for this decision … any new item must work with at least three items already in my closet (this criteria works well for separates but not so much for dresses). This also works for shoes … if you can’t wear them with at least three outfits you already own … send them back. #alwaysexceptionsforshoes #ihopemyhusbanddoesntreadthis

Some of the links are affiliate links, which means that if you click on one of them and make a purchase, I could receive a small commission at no cost to you. Thanks for the support!

The BOLD Skirt

First up, the red Hugo BOSS skirt I waxed poetic about from the Nordstrom sale. I was driving home dreaming about all the outfits I could create with this little number. Below are just three of the many I came up with.

This is the perfect skirt for color blocking. The bold red hue is just asking for more bold color and almost any color works. For the ambitious go bright blue or yellow like I did. For the daring try pink or orange. And if you want more subtle choose baby blue, ivory, black or navy. All of these colors work and would look gorgeous with the red. While not required (as you will see with the second shirt), tuck the shirt to showcase your waist and the wrap detail.

Electric Blue Top | Hugo Boss Skirt

But the skirt isn’t limited to solids …

Rebecca Taylor Floral Top | Hugo Boss Skirt

This floral top uses the same red skirt to be either more formal OR more casual. #saywhat

The blouse is inherently more casual but with a structured skirt you have a very work appropriate look. Add a suit jacket (or blazer) and you’ve now got a formal look for work.

Rebecca Taylor Floral Top | Hugo Boss Skirt | Hugo Boss Jacket

The Summery Skirt

This next skirt I had been drooling over for awhile. Nothing says summer like white (or Ecru as the case is here).

Electric Blue Top | Ann Taylor Skirt (similar)

If we remix the bright blue top, you have another great look – totally different than the blue and red. ANY solid color top works and I would again keep it tucked to highlight the waist. Try to avoid lots of details with the top as I think this skirt looks better with clean lines. You can see it with a “pouffier” top here – and while this balances the pouf of the skirt – I feel something fitted looks better. #youbeyouthough

Electric Blue Top | Ann Taylor Skirt (similar) | Cropped Blazer (similar)

If I add a jacket to this, I’ve now upgraded the look to business formal. With the full circle skirt you need to go with a cropped jacket. Having the jacket hit at the widest portion of the skirt will make you look your widest. #notgood  Having the jacket hit at the smallest point (your waist) will highlight your hourglass. #allgood

Emerson Rose Top | Ann Taylor Skirt (similar)

For this look, I styled a more casual top. I love the mix of warm and grey tones on this top and the fact it can dress up or down. It’s similar to a T-shirt but the upgraded material allows you to be office appropriate.  It also comes in white for those feeling a little less abstract.  It has a tie that you can see in the pictures below but this skirt looks better with the shirt tucked.

The Casual Skirt

Both of the patterned shirts above are more casual so they dress down very easily. Below you can see both of these tops with a denim skirt. And the effect is similar with jeans or shorts.

Rebecca Taylor Floral Top | Denim Skirt (similar)

Emerson Rose Top | Denim Skirt (similar)

Wardrobe Mixing

Learning to mix and match a wardrobe is not hard – just keep a few things in mind …

  • It’s much easier to downgrade an item than upgrade. I can wear the blue draped blouse with denim and be appropriate for lots of functions but adding a cotton T-shirt to the red skirt isn’t going to get me to work. #dresscode
  • If you want pieces that will multitask pay attention to the material. As noted it is very hard to dress up a cotton T-shirt but if you get a silk blend or linen shirt cut like a T – you will have many more options. 
  • For beginners solids are much easier to mix than prints. A solid is always going to go with another solid. It’s not impossible to successfully mix patterns but there is a whole other set of rules to follow. (See here for ideas to try on that subject).
  • Lastly, shoes (my favorite). Most of these photos did not include my shoes … somewhat purposefully. Changing shoes can dramatically change an outfit. Add heels and your going to upgrade the look. Switch to sandals or sneakers and you will downgrade.

These are just some simple guidelines … the most important … have fun!