How to Style a Plaid Skirt (Modest Outfit Ideas)

Every fall I pull out my plaid skirts and remember why I love them. A long plaid skirt does half the work of an outfit for you. The pattern already has three or four colors in it, so picking a top is easy: you just match one of them.

Here's how I choose a plaid skirt and the ways I wear mine all season.

What to look for in a modest plaid skirt

A few details decide whether a plaid skirt feels cozy and polished or stiff and costume-like.

• Length. A midi that hits mid-calf or lower, or a full maxi. Sit down in it and make sure the hem still covers your knees.
• Shape. A-line and pleated skirts move nicely and give room to walk. A straight pencil cut looks sharp but usually needs a slit, so check how high it goes.
• Fabric. Wool and wool blends hang well and keep you warm. Flannel is soft and casual. Thin polyester plaid can look shiny, so check it in daylight.
• Pattern size. Small checks read almost like a solid from far away and are easy to wear. Big bold tartans make a statement, so keep everything else simple.
• Lining. A lined skirt doesn't cling to tights and won't itch. It's worth checking before you buy a wool one.
• Waistband. A flat front waistband sits smoothly under sweaters. An elastic back is comfortable for long days and Yom Tov meals.

Start with the colors in the plaid

This is the one trick that makes plaid easy. Look closely at your skirt and pick out the colors in it. Then build the outfit from those colors only.

• A camel and cream plaid works with a cream sweater, camel coat and brown boots.
• A navy and green tartan works with a navy knit, a cream blouse or a forest green cardigan.
• A red and black plaid looks great with a black turtleneck and black boots, or softened with a cream sweater.
• A gray glen check goes with almost anything: black, white, camel, burgundy or soft pink.

If you're not sure, a solid top in cream, black or the darkest color in the plaid always works.

The cozy sweater look

This is my everyday plaid outfit from October through February.

• A fitted crewneck or turtleneck in a solid color from the plaid
• Tuck it in or leave it out if it's a short, boxy sweater that hits at the waist
• Tights and ankle boots or loafers

A cream cable-knit sweater with a camel plaid skirt is my favorite. It looks warm and put together without trying.

Blouse and cardigan

For work or a meeting, a blouse makes a plaid skirt look more polished.

• A high-neck blouse or a button-down buttoned to the collar
• A long cardigan or a fitted cardigan over it
• Loafers, ballet flats or low block heels

A bow blouse with a small check skirt is a classic look that never feels dated. Keep the blouse a solid color so the two don't fight.

Dressing it up for Shabbos and Yom Tov

Plaid can absolutely be dressy. A few changes do it.

• Pick a wool plaid with a soft sheen or a pleated maxi
• Wear a silky blouse or a fine knit in a rich color like burgundy, emerald or navy
• Add a thin belt, pearl or gold earrings and a pair of heels or polished boots

A deep green tartan skirt with a black velvet top is perfect for Chanukah parties. It feels festive without being too much.

Layering for real cold

Plaid skirts are made for winter, so layer them up.

• Opaque tights in black, brown or charcoal, or fleece-lined tights on very cold days
• A turtleneck under a sweater or a sweater vest
• A long wool coat that covers most of the skirt, or a short jacket that ends at the waist

When the coat is long, make sure it's a little longer than the skirt or clearly shorter. Coats that end just above the hem can look cut off.

Which shoes go with a plaid skirt

• Ankle boots are the easiest and work with any length.
• Knee-high boots look great with midi skirts and keep your legs warm.
• Loafers with tights feel smart and a little preppy.
• Ballet flats look sweet with small checks and pleats.
• Sneakers make a flannel plaid skirt feel relaxed for weekends.

Match the shoes to the darkest color in the plaid or go with classic brown or black.

Mixing plaid with other patterns

This takes a little practice, but it can look great.

• Keep one pattern big and the other small, like a bold tartan with a thin stripe.
• Make sure the two share at least one color.
• If you're unsure, stick to a solid top. It's never wrong.

Easy plaid skirt outfit formulas

1. Plaid midi skirt plus cream turtleneck plus brown ankle boots plus camel coat
2. Plaid maxi skirt plus navy crewneck plus loafers plus wool scarf
3. Small check skirt plus bow blouse plus long cardigan plus ballet flats
4. Tartan maxi skirt plus black velvet top plus pearl earrings plus heels for a holiday party
5. Flannel plaid skirt plus chunky sweater plus sneakers for a weekend walk
6. Plaid pleated skirt plus sweater vest over a button-down plus knee-high boots

Caring for a wool plaid skirt

• Hang it on a clip hanger by the waistband so the pleats stay sharp.
• Brush it with a soft clothes brush after wearing instead of washing it every time.
• Spot clean small marks and dry clean when needed, or follow the care label.
• Steam it to release wrinkles rather than pressing hard with an iron.

The bottom line

A long plaid skirt is one of the easiest pieces to style because the colors are already chosen for you. Pull one color from the pattern for your top, add tights and boots, and you're dressed. Start with a small check or a neutral camel plaid, and once you love it, try a bolder tartan for the holidays.

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