How To Wear A High Waisted Skirt

plaid skirt black over the knee boots fall outfit gray wool hat

Skirt: c/o ModCloth plaid high waisted skirt (size XXS) | Sweater: c/o ModCloth charter school black turtleneck (size XXS) | Hat: c/o ModCloth museum hopper hat | Boots: c/o Crisintha over the knee boots | Purse: c/o Stewart little joy

I keep thinking if I wear fall clothes, maybe just maybe the weather will start getting cooler in Newport Beach?  We are getting yet another heat wave.  This clearly isn’t stopping me from wanting to wear fall clothes.  I love how playful and feminine this outfit is.

plaid skirt black over the knee boots winter outfit gray wool hat

This plaid skirt is everything!  I absolutely adore it to pieces.  It’s simple, very well made and has pockets!  The perfect skirt for fall and the upcoming holidays.  The material is a soft, tweed like fabric and fully lined.  There is no stretch so make sure to keep this in mind when ordering.  I’m so happy it’s machine washable – no dry cleaning bills!

plaid skirt black over the knee boots winter outfit gray wool hat

Sizing runs small so I’d recommend sizing up.  I’m wearing size XXS and the waist measures 12″ laying flat cross and total length is 18″.  It’s not as short as you may think.  It appears much shorter because of my over the knee boots but it’s actually a great length for petite gals.

plaid skirt black over the knee boots winter outfit gray wool hat

The subtle plaid print is simple and classy.  You can wear it with tights and pumps for work or ankle booties for a more casual look.  The best part about this skirt?  No alterations needed.  Yay!  Would highly recommend!

plaid skirt black over the knee boots winter outfit gray wool hat

I’ve been looking for a black turtleneck and this one fit the bill.  It’s the same material as my favorite ModCloth charter school cardigans that I own in several colors  and LOVE (see HERE).  Sizing runs true to size.  I have on size XXS and it fits me well.  This is a great basic to have that will be easily mix and match with other items in your wardrobe.  It pairs perfectly with this skirt and topper hat.

plaid skirt black over the knee boots winter outfit gray wool hat

If you’re new to the blog or haven’t heard of ModCloth – they’re one of my favorite places to shop. They carry unique, modest and vintage-y clothes and accessories.  I started shopping here back in 2010/2011 and haven’t stopped since!  Sizes range from XXS to 4X so there’s a wide range of different sizes to meet everyone’s needs.

plaid skirt black over the knee boots winter outfit gray wool hat

Some of my all time favorite pieces are from ModCloth.  Here are some items I own and LOVE (everything is currently in stock):

ModCloth Favorites

FYI – this plaid dress and plaid skirt are back in stock!  I have both and they’re perfect for the holidays.

plaid skirt black over the knee boots winter outfit gray wool hat

There are so many cute new arrivals that I have my eye on!  Here are my top picks:

ModCloth New Arrivals

plaid skirt black over the knee boots winter outfit gray wool hat

How To Wear A High Waisted Skirt

1. Tuck in your top – High waisted skirts look best when your top is tucked in.  This helps create a cinched waistline and gives you a great silhouette.  Try pairing your skirt with a fitted, thinner top so that it bunches up less. **helpful hint: tuck your top in your underwear to keep your shirt in place**

2. High neck top – Turtlenecks makes any outfit look sophisticated and elegant.  It keeps the outfit modest yet stylish and just looks very classy. Mocknecks work well too.

3. Crop top – Try pairing your high waisted skirt with a crop top.  This doesn’t necessarily mean you have to show your midriff.  I would highly recommend these dream of the crop cardigans.  They look amazing with high waisted skirts.  I have them in multiple colors and would highly recommend.

4.  Add a belt – Adding a belt can really pull an outfit together.  It helps cinch and define your waist plus belts are so much fun!

5. Wear heels – I typically would recommend wearing heels with your high waisted skirt but in this case, my flat boots work well because the skirt is fuller and more playful.  You’ll definitely want to wear heels with pencil or midi skirts.
plaid skirt black over the knee boots winter outfit gray wool hat

Skirt: c/o ModCloth plaid high waisted skirt (size XXS) | Sweater: c/o ModCloth charter school black turtleneck (size XXS) | Hat: c/o ModCloth museum hopper hat | Boots: c/o Crisintha over the knee boots | Purse: c/o Stewart little joy

As soon as the weather cools down, I’ll be wearing this skirt, turtleneck and hat on repeat.  I love when an outfit is super comfortable yet still stylish and makes you feel good. 🙂

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  1. Hi, did you get a 1/2 up when you purchased the Crisintha over the knee boots? Many of the reviews on these boots recommend sizing up and I want to make sure I am getting the right size.

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