Style and Styling

Skirt Style: 7 Ways


Happy day, Reader Dearest!

I was scrolling through my Instagram feed a week or so ago and ran across a style challenge…

Gail of Is This Mutton? was playing around with a #7dayskirtstylechallenge.

In Which: (Winnie-the-Pooh reference!)

You wear a skirt (or skirts) for 7 days in a row.

You know me.

I’m always up for a good style challenge. (Read why at the link.)

I mean, how hard could it be?

(Insert knowing laughter, here.)

Well, you’ll see…

Day 1: Pencil + Tee + Boots + Scarf + Moto

This outfit felt like a cliche! Scarf, Beret, Striped Top. I have to admit it was fun even if it felt like a costume!

Day 2: Midi + Belted Sweater + Boots

A summer skirt made to work overtime with boots and a belted wool sweater to create shape. And yes, I added a bandana for a little color near my face. Because every day needs a little color!

Day 3: A-Line + Blouse + Tights/Booties + Scarf

Hog wild on color today! It was the first day of my Winter Capsule, so I added my red skirt and broke out a bright pink blouse to add some cheer to the grey days to come. I’m sticking with the same basic capsule inspo I used for fall with a few shifts. (Watch more about that, here.)

Day 4: Denim Midi + Denim Shirt + Flats

Little did I know this would be the beginning of a little 3 Day Style Train!

Buying something new to get through a style challenge is NOT my M.O. In this case, however, a denim skirt seemed like a good piece to try out. I felt very 80’s standing there in the dressing room at Target…

In the late 80’s, I wore an acid washed midi-pencil skirt (flat front, slit in the back) on my plane flight when moving to Athens. Greece, that is, not Georgia. The in-flight film was The Princess Bride; I laughed out loud all the way through. (And still do!) The man sitting next to me was not impressed. He didn’t seem to get any of the humor. I do not think that means what you think it means… Bless his heart.

Day 5: A-Line + Denim + Boots

The shirt is on repeat. This was perfect for coffee and breakfast with friends. The purple flower? Color for my portrait area and the first Sunday of Advent! (Still obsessing about these patently faux flower brooches!)

Day 6: A-Line + Blouse + Denim jacket + Boots

Today, the skirt and boots are on repeat. (Just in case you missed them! lol) I wore this same skirt and blouse combo ages ago and loved it. Why I didn’t repeat it sooner? Beats me!

Day 7: A-Line + Cami + Cardie + Tights/Booties

Channeling some warm and cozy winter vibes? This pearl pile is as close as I’ll get to snowballs. My red flannel skirt, tights and booties are making all the statement. Again. I wish the bottom of this cami had some shaping; the straight bottom is not very flattering. (I rarely wear it as a top; it’s usually hidden under a sheer blouse providing coverage.

I’d wear this same bottom combo with my denim shirt, too. Or my light blue silk and a greeny blue cardie. SO many options! No, I won’t wear them with black. I have a negative association with red and black paired together. (Call it a Dawg trauma response.)

For a little style TnT, I went for a super bright red lip. Not that you can tell from a distance!

Lessons Learned

I really struggled… With jeans withdrawal. Grabbing a denim skirt or shirt just isn’t the same as sliding into my trusty old Levi’s. I did not realize how much a part of me they are. Wearing jeans seven days in a row was much easier than not wearing them seven days in a row!

Stripes, a Scarf AND a Beret is TOO MUCH.

I love boots with skirts, however a cute pair of red flats to wear with my red skirt and tights would give me a lot more style mileage.

Red tights and booties will put a smile on anyone’s face. So will silver boots.

As much as I love my heels, I am looking forward to flats tomorrow!

How About You?

If you want to see more skirt style, check out Gail’s post featuring nine other women in their skirts! For many women, skirts are much easier to fit than trousers! If that’s you and you struggle because the proportions always feel off, you’re not alone. Think of a skirt like shorts–watch your thirds and the colors! Are you a skirt wearer? What’s your favorite silhouette? Is one season more skirt-y for you? Which? Do any of these looks make your heart sing? Do tell! There’s plenty of room in the comments below…

Stylishly yours,


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