Now & Later | Plaid Skirt

You might not realize this, but my closet is full of mostly classic, timeless pieces. No really, there’s not a lot of trendy, one-season pieces! It’s how I pair and accessorize them that makes them different.

It’s always been one of my favorite challenges to mix-and-match pieces to create as many different looks as possible. This pastime dates all the way back to Junior High, when I was working with a much smaller wardrobe, and an unrealistic goal of never repeating outfits! In fact, that’s why the majority of my style posts center around multiple ways…or Five Ways in many instances!

Today I’m excited to share two very fun, yet very different, ways of styling a classic plaid skirt. The a-line shape and flirty length give it an updated appeal, and easy to transition for both Now & Later.

Striped Shirt (similar for less) | Plaid Skirt | Similar Leopard Pumps | Bag (similar for $25!) | Pearl Cluster Necklace | Earrings

For Now, while the days are still mostly warm, I paired it with a classic button-down top and statement jewels. Even though both the shirt and skirt are classic pieces, pairing the stripes and plaid keep them from looking too stale. And a pop of leopard is always a good idea!

Striped Shirt (similar for less) | Plaid Skirt | Pearl Cluster Necklace | Earrings

I love how the bag and pearls give the outfit an overall proper vibe (perfect for work), but the mix of patterns keeps the look fun.

Striped Shirt (similar for less) | Plaid Skirt | Similar Leopard Pumps | Bag (similar for $25!) | Pearl Cluster Necklace | Earrings

Once the weather cools even more, I’ll add a fitted sweater (to balance the fullness of the skirt), and cover my legs with tights. The head-to-toe black is chic, but adding the punchy bag and fun earrings make the outfit interesting.

Turtleneck | Plaid Skirt | Opaque Tights | Tassel Earrings | Yellow Bag | Sunglasses | Similar Pumps

Sugarplum Style Tip: For extra slimming, make sure your tights are super-opaque…you don’t want any skin peeking through. These have just enough control top, are super dark, and are comfortable thanks to the lycra. I do size up to a small.

I hate when I have a particularly cute outfit, and am forced to cover the whole thing with a coat! But what if your coat is just as cute as the outfit!? This one creates an hourglass shape with the tie-belt and a-line shape. And don’t get me started on the tall collar and high-low hem!! It comes in the best leopard print, too, if you dare!

Fit Tip: The coat runs true to size, I’m wearing an XS with enough room to layer underneath.

CoatTurtleneck | Plaid Skirt | Opaque Tights | Tassel Earrings | Yellow Bag | Sunglasses | Similar Pumps

This skirt had me plaid and pockets, plus the colors are easy to pair for a number of different looks. ModCloth is a great resource for both classic and vintage-inspired pieces, and the quality is spot-on. Plus, their sales are amazing, and they offer a wide range of sizes (usually XXS to 4X), making great style accessible for all of us.

Fit Tip: Tops and coats from ModCloth are true to size for me, but I need to size up in skirts with fitted waists. I’m wearing a small in this one.

Turtleneck | Plaid Wool Skirt | Opaque Tights | Yellow Bag | Similar Pumps

CoatTurtleneck | Plaid Wool Skirt | Opaque Tights | Tassel Earrings | Yellow Bag | Sunglasses | Similar Pumps

I’m so excited to wear this (fully-lined) skirt for the next two seasons, and can hardly wait for a real chance to wear the coat (without sweating!). What pieces are you most excited to pull out of hiding? See more Now & Later styles here, and more Work Wear here.


{Shop My ‘Now’ Style}

{Shop My ‘Later’ Style}


*Photos by the darling & talented Mary Summers. This post is created in collaboration with ModCloth, but all opinions, styling, and extreme popped collars are my own. Thank you for supporting Hi Sugarplum sponsors!*




Leave a Comment


  1. You really can’t go wrong with a classic grey plaid skirt. It’s so timeless, and super cute. Love the way you wore it with the coat.

    Charmaine Ng | Architecture & Lifestyle Blog

    Posted 10.24.17 Reply
  2. Sandy wrote:

    Does a striped button down shirt, or black turtleneck ever go out of style? Never!
    Nice combos, C.! And those black patent leather chunky heel pumps are yummy!

    Posted 10.24.17 Reply
  3. Sandy wrote:

    Ps- you remind me of a favorite (fashionista) co-worker I once worked with. I would beg for her permission to go out and buy what she was wearing. I rarely had to shop around, just go straight to the source for what she was wearing. Fast and easy! : )

    Posted 10.24.17 Reply
    • Cassie wrote:

      Ha!! I’m thrilled to inspire you!! I do the same with my friends, too! “Where’d you get this?!?!? I need it!!”:) xo

      Posted 10.24.17 Reply
      • Sandy wrote:

        “Gotta have it!”

        Posted 10.24.17 Reply
  4. These outfits are great. BUT THAT COAT!!!!!!

    Posted 10.24.17 Reply
  5. Classic pieces are definitely the way to go. I love your pairing of stripes and plaid.

    Posted 10.24.17 Reply
  6. I LOVE all the print mixing in your ‘wear now’ outfit. So chic! But I’m also a sucker for a black turtleneck, skirt, and black tights for winter. It’s such a classic look and can have a different look and feel depending on the skirt and accessories. Great coat too!

    Posted 10.24.17 Reply
  7. Gail W. wrote:

    I love how you don’t feature a lot of trendy, one-hit wonders that languish in your closet after one season. I used to dress like this post everyday – crisp blue Oxford shirts with grey trousers or a black pencil skirt, statement necklace and classic black bag. Makes me want to light a match to my current closet!!

    Posted 10.24.17 Reply
    • Cassie wrote:

      Thanks so much, Gail! I’m too ‘frugal’ to buy things that won’t stand the test of time!! I like to mix things up too much to have to ditch something after a season or two. I’m thrilled you find inspiration here! xo

      Posted 10.24.17 Reply
  8. Joanna wrote:

    I love both looks! You are the star at mixing patterns. The striped shirt and leopard shoes make the skirt fun while looking business like.
    That coat is very stylish. But… the wrinkles! Is that from being packaged during shipping or just from sitting?

    Posted 10.24.17 Reply
    • Cassie wrote:

      Thanks so much!! I noticed those wrinkles too, ack!! It’s probably a little of the packaging and sitting…it’s a wool coat, so I expect it to relax once it’s been hanging a bit! xo

      Posted 10.24.17 Reply
  9. Love how you styled those pieces Cassie- they look great on you!

    Posted 10.24.17 Reply