How to Style an Olive Skirt: Modest Outfit Ideas for Fall and Winter

An olive skirt is one of those pieces that quietly works with almost everything. It's earthy and soft, a little more interesting than black or navy, and it looks lovely all through fall and winter.

Olive sits between green, brown and grey, so it acts almost like a neutral. Here's how I style mine for everyday, work and Shabbos.

Know your shade of olive

Olive comes in a few different moods, and each one pairs a little differently.

• Classic olive. A muted green with a hint of brown. The most versatile, and lovely with cream, camel and rust.
• Khaki. Lighter and sandier. It feels relaxed and pairs well with white, denim and navy.
• Moss. Deeper and a little more green. Beautiful with chocolate brown, burgundy and gold.
• Army or dark olive. Almost brown. It feels grown-up and works like a soft alternative to black.

If you're buying just one, a classic olive midi or maxi in a fabric with some weight is the easiest place to start. It hangs nicely and covers well.

Skirt styles to look for

• A-line wool midi. Warm and structured for cold weekdays. See how to style a long wool skirt.
• Corduroy skirt. Casual and cozy for weekends. More ideas in how to style a corduroy skirt.
• Satin or silky maxi. An olive satin skirt looks rich and dressy for Shabbos. See how to style a satin skirt.
• Pleated midi. Soft movement that balances a chunky knit. See how to style a pleated skirt.
• Utility or cargo maxi. Relaxed and practical for errands, as long as it's long and not too slim.
• Tiered maxi. Light and swishy, nice for milder fall days.

For modest dressing, look for a length that reaches mid-calf or longer, a lining if the fabric is thin, and enough fullness that the skirt doesn't cling when you walk or sit.

Colors that go with olive

Olive is earthy, so it looks best next to other warm, natural shades.

• Cream and ivory. The softest pairing. A cream sweater with an olive skirt looks calm and elegant. See how to style a cream sweater.
• Camel and tan. Rich and autumnal. A camel knit or coat over olive always looks put together.
• Rust and terracotta. Warm and pretty, like fall leaves. My rust sweater guide has more.
• Chocolate brown. Deep and cozy, especially with moss or dark olive.
• Burgundy. A lovely jewel-tone contrast. See how to style a burgundy sweater.
• Black. Sleek and simple, good for work.
• Blush. Unexpected but soft and feminine with khaki or light olive.
• Denim. A chambray shirt with a khaki skirt feels relaxed and easy.

For more color ideas, see winter color combinations.

Tops and sweaters

• Fine-knit turtleneck. Covers the neckline and tucks in neatly. See how to style a turtleneck.
• Chunky cable knit. Cozy for weekends. Keep the skirt simple so the outfit doesn't feel bulky.
• Button-down or blouse. A cream or white shirt tucked into olive looks crisp for the office.
• Long-sleeve tee. The easiest everyday top. A striped tee is cute with khaki.
• Sweater vest over a blouse. A camel or cream vest adds a polished, slightly preppy touch.

Tucking a top in shows off the waist of the skirt. If you'd rather not tuck, choose a top that skims the hip so the proportions stay balanced.

Layers for cold days

• Camel coat. The easiest coat over olive. See how to style a camel coat.
• Cream or oatmeal cardigan. Soft and easy to throw on.
• Quilted jacket. A brown or black quilted jacket looks great with olive for country walks. See how to style a quilted jacket.
• Denim jacket. Casual and fun with a khaki skirt.
• Blazer. A camel, brown or black blazer works well at the office.

Shoes and tights

• Brown boots. Brown ankle or knee-high boots look natural with olive. See ankle boots with long skirts.
• Cognac or tan. Warm and pretty, especially with khaki.
• Black boots. Sharper and a little more city.
• Loafers and ballet flats. Great for the office and Shabbos.
• Sneakers. Fine for a weekend utility or tiered skirt.
• Tights. Brown or olive tights blend with boots, and skin-tone tights feel lighter with flats. More in how to choose tights for long skirts.

Accessories

• Gold jewelry. Gold looks warm and lovely next to olive.
• Pearls. A simple strand over a cream knit is instantly dressier. See how to style pearls.
• Headscarf or snood. Cream, camel, rust or a print with olive in it all work beautifully. See how to match a headscarf to your outfit.
• Scarf. A rust, camel or cream scarf adds warmth around the face.
• Bag. A tan, cognac or brown leather bag keeps everything warm and cohesive.

Outfit ideas

1. Weekday classic. Olive wool A-line midi, cream turtleneck, camel coat and brown suede ankle boots.

2. Cozy weekend. Olive corduroy skirt, chunky rust cable-knit, brown knee-high boots and a cream headscarf.

3. Shabbos table. Moss satin maxi, ivory silk blouse, pearls, gold earrings and simple flats.

4. Office day. Dark olive pleated midi, black fine-knit crew, black blazer and loafers.

5. Fall walk. Khaki utility maxi, striped long-sleeve tee, denim jacket and white sneakers.

6. Soft and pretty. Light olive tiered skirt, blush sweater, skin-tone tights, ballet flats and a blush snood.

Common mistakes to avoid

• Too much green. Olive with a bright green top can feel overwhelming. Let olive be the only green, or pick a much softer shade.
• Cold greys. Olive next to a cool, blue-grey can look a little drab. Warm neutrals usually look better.
• Clingy fabric. A thin, stretchy olive skirt can cling. Choose a heavier fabric or add a slip.
• Too casual. A cargo skirt with a hoodie can look sloppy. Add a knit, a nicer bag or leather boots to lift it.

Quick questions

What color top goes best with an olive skirt?

Cream, camel, rust, white and black are the easiest. Burgundy and blush are lovely when you want something softer or dressier.

Can I wear an olive skirt to Shabbos?

Yes. A moss or olive satin or wool maxi with an ivory blouse, pearls or gold jewelry and simple flats looks elegant.

Does olive go with navy?

It can, but it's a subtle pairing. Cream, camel and brown are usually easier and warmer.

An olive skirt is a quiet workhorse in a modest wardrobe. Pair it with cream, camel or rust, keep the accessories warm, and you'll find yourself reaching for it all season.

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