How to Style a Long Denim Skirt: Easy Outfits for Every Season

If I could only keep one casual skirt, it would be a long denim skirt. It goes with sneakers and a sweatshirt on a Sunday, with a crisp shirt and loafers on a weekday, and with a chunky sweater and boots all winter. It hides wrinkles, survives kids and spills, and looks better the more you wear it.

The trick is choosing the right one and knowing a few easy outfit formulas. Here is everything I have learned.

Pick the right cut

Long denim skirts come in a few main shapes, and each one gives a different look.

• A-line. Fitted at the waist and gently flaring out. This is the easiest shape to wear and the most flattering on most bodies. It moves well when you walk and doesn't cling.
• Straight or column. Narrow from hip to hem. It looks sleek and modern, but it needs a slit or a kick pleat so you can walk comfortably. Check that the slit is low enough for you before you buy.
• Front-button or button-through. Buttons all the way down the front. It has a softer, vintage feel. If the bottom buttons open, you can sew them closed to the height you want.
• Tiered or gathered. Softer, lighter denim with seams across the skirt. It feels more like a casual summer skirt and pairs well with simple tees.

If you are buying your first one, start with an A-line. It works with the most tops and shoes.

Choose the length for your height

A long denim skirt usually means midi (mid-calf) or maxi (ankle). Both work, but they look different with shoes.

• Midi hems that hit at the narrowest part of your calf are the most flattering. They show a bit of leg or tights, so they look great with loafers, ballet flats and tall boots.
• Maxi hems that skim the ankle look relaxed and easy. They pair well with sneakers and ankle boots, since the shoe tucks right under the hem.

If you are petite, a maxi that ends just above the ankle bone keeps you from looking swallowed up. If you are tall, check the length in the listing carefully, because many "maxi" skirts land at mid-calf on taller women. I wrote more about this in my guide to midi vs. maxi skirts by height.

Choose the wash

The color of the denim changes how dressy the skirt feels.

• Dark indigo is the most versatile. It looks polished enough for work and errands, and it hides stains. If you own only one, make it dark.
• Medium blue is relaxed and classic. It feels like your favorite jeans in skirt form.
• Light or vintage wash looks summery and casual. It's lovely with white sneakers and soft colors.
• Black or gray denim is the dressiest. It goes with almost any top and looks great in winter.

Pay attention to the fabric too. Denim with a little stretch is more comfortable for sitting all day, while 100% cotton denim holds its shape better and softens over time.

Five easy outfit formulas

### 1. The weekday classic

Dark denim skirt, a tucked-in button-down shirt, and loafers or ballet flats. Add a belt if the skirt has loops. This is my go-to when I want to look put together without trying hard.

### 2. The errand uniform

Medium-wash skirt, a long-sleeve tee or a fitted shell, and clean white sneakers. Throw on a denim or utility jacket in a different shade, or a cardigan. It's comfortable enough for a full day of carpools and shopping.

### 3. The cozy fall look

Any wash with a chunky knit sweater, opaque tights and ankle boots. Tuck just the front of the sweater into the waistband so you don't lose your shape. My winter layering guide has more ideas for keeping this look warm.

### 4. The softer, prettier version

Light-wash skirt with a blouse that has a little detail: puff sleeves, a ruffle collar or a small print. Finish with ballet flats or simple sandals in summer.

### 5. The dressed-up denim

Black or very dark denim with a silky blouse or a fine-knit sweater, a long necklace and heeled boots or pointed flats. It works for a casual Shabbos lunch, a school event or dinner out.

Tops that work best

Because denim is a heavier fabric, the top should balance it.

• Fitted or tucked tops keep the outfit from looking bulky. A long, loose top over a full skirt can look shapeless.
• Layering shells under looser tops give you extra coverage at the neckline and sleeves without adding bulk. See my post on layering slips and shells.
• Cropped sweaters and jackets that end at the waist show off the skirt's shape.
• Stripes, gingham and white always look fresh with blue denim.

Shoes for every season

• Spring and summer: white sneakers, ballet flats, simple sandals.
• Fall: loafers, ankle boots, low block-heel boots.
• Winter: tall boots with a midi, or ankle boots and warm tights with a maxi.

If you're not sure which boots work with which length, my fall shoe guide breaks it down.

How to make it last

A good denim skirt can last for years if you treat it kindly.

• Wash it less. Denim doesn't need washing after every wear. Air it out and spot clean small marks.
• Wash it inside out in cold water to keep the color from fading quickly.
• Skip the dryer when you can. Hang it to dry so it doesn't shrink or lose its shape, especially if it has stretch.
• Check the slit and the hem. If a slit starts to tear at the top, a few stitches will save it.

Shopping tips

• Check the length in inches, not just the word "maxi" or "midi." Measure a skirt you already love from waist to hem and compare.
• Look at the slit placement in the photos and the product details.
• Read the fabric content if comfort matters to you. A small amount of elastane makes a big difference for sitting.
• Try secondhand. Denim ages well, and thrift stores and resale apps are full of long denim skirts. My guide to telling quality clothing will help you spot the good ones.

A long denim skirt is one of those pieces you stop thinking about because it simply works. Pick a shape and wash that fit your life, and it will carry you through every season.

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