Between Thanksgiving dinners, Hanukkah celebrations, office parties and family gatherings, the holiday season brings plenty of occasions to dress for. The good news? You probably already have much of what you need.

This year's dates: Thanksgiving is Thursday, November 26, 2026 (OPM). Hanukkah begins at sundown on Friday, December 4, and ends at nightfall on Saturday, December 12 (Hebcal). The first night falls on Shabbat, so an outfit that works for both is a help.

Four checks before you leave the house

Before choosing a holiday outfit, try these four quick checks. They're especially helpful when you're wearing layers or planning to sit, cook or move around for several hours.

1. Lean forward as if you are serving. Does the neckline stay where you want it? If not, a higher neckline layer underneath can solve it without another full shirt.
2. Check your sleeves. Holiday days involve dishes, candles and carrying things. Sleeves that stay out of the way save a lot of tugging.
3. Sit down. Check that the hem still covers what you want covered when you are seated at a table or on a low couch.
4. Take the cardigan off. If the room gets warm, does the top still look finished on its own? If it only works with the cardigan, you will be stuck in it all evening.

Hosting Thanksgiving

Hosting means hours of bending, lifting and leaning over the table.

• Choose a comfortable stretch skirt that lets you bend, crouch and move easily. An A-line skirt gives you more room around the knees, such as the Knee Length A-Line Skater Skirt, while a stretch pencil skirt like the Women's Stretch Maxi Pencil Skirt (also in plus size) can also work if you can move comfortably in it.
• Pair it with an elbow-length or three-quarter-sleeve top that stays clear of food preparation and washing up, such as the Fitted Layering Shell with Elbow Sleeves (plus size) or the Essential 3/4 Sleeve Crew Neckline Shell (plus size).
• Pick darker colors or prints if you will be near gravy and cranberry sauce.

Guest at a holiday dinner

A mid-calf or longer skirt can be a comfortable choice for dinner. Check where the hem falls when you're seated, especially if the chairs or couches are low.

• The Mid-Calf Pencil Skirt in Cotton Spandex (plus size) pairs with a festive top or sweater you already own.
• If your favorite holiday top has a lower neckline, add the TeeNeck crew collar neckline layer underneath instead of a whole extra shirt.
• For more on this length, see our guide to the midi hemline.

Travel day

Long drives, airports and train rides call for pieces that stay comfortable while you sit for hours and reach for overhead bags.

Planes and airports can be cold, while cars and terminals can be warm. Choose layers that are easy to remove without changing your coverage. A lightweight cardigan or zip-front sweater is often easier to manage than a heavy pullover. For long journeys, check that your waistband stays comfortable when you're seated for several hours.

• A knee-length stretch pencil skirt, such as the Women's Stretch Knee-Length Pencil Skirt (plus size), is easy to sit in. Tights or leggings underneath are an option for extra warmth.
• If your top rides up when you reach for a bag, the Hippies waist coverage band keeps your midsection covered.
• Our winter skirts and boots guide covers what to wear with each skirt length.

Hanukkah party

Whether you're making latkes, lighting candles or visiting family, choose sleeves that won't get in your way. Elbow-length or fitted three-quarter sleeves are practical around food preparation and open flames.

• The Fitted Layering Shell with Elbow Sleeves (plus size) works under a sweater or jumper, or alone.
• For a dressier look, wear a lace top or dress over a layering piece. Our lace layering guide shows how.
• This year the first night is a Friday, so a Friday-evening gathering may call for an outfit that works for both Shabbat and Hanukkah.
• With eight nights, you may go to more than one gathering. Rotate a few tops over the same skirt rather than buying a new outfit for each night.

Office or holiday party

Start with a skirt or dress you already feel comfortable wearing to work, then add one festive element: a dressier blouse, a lace layer, a colorful cardigan or jewelry.

If you're wearing a sleeveless dress, a fitted layering top can add sleeves without changing the overall look; the Modest Layering Dress with 3/4 Sleeves (plus size) adds sleeves and length in one layer. If the neckline is the only concern, a neckline insert or a cropped layer may be enough, such as the Crop Top 3/4 Sleeve with Jewel Neckline (plus size) or the Sleeveless Crop Tank with Modest Neckline.

For a party where you'll be standing or sitting for several hours, choose shoes you can comfortably wear all evening. More ideas are in Layering It Up, Layering It Down.

Holiday gift ideas

Clothing makes a great gift, and a tricky one. Is the size right? The style? Can she return it? Does she already own it? If she dresses modestly, add coverage to the list.

Unless you know she'll love a holiday-themed sweater, consider something she can wear all year. A comfortable layering top, scarf or cardigan will probably get more use than a dreidel cardigan or reindeer sweater.

Before buying clothing as a gift, check three things:

1. Her preferences: Does she usually wear skirts, dresses, or both? What sleeve lengths and necklines does she prefer? And does she already own something just like it?
2. Her sizing: If you're unsure, check the measurements of something she already owns rather than relying only on the size label.
3. Returns: Check the return policy before ordering, especially for gifts purchased well ahead of the holiday.

Basics are a safe gift. When you're not sure what to give someone, everyday basics are often a better choice than something unusual. A comfortable layering top in a color she already wears is a gift she can use throughout the year. A layering tank like the Premium Sleeveless Layering Tank with Full Shoulder Coverage (plus size) makes more of her wardrobe wearable.

For someone whose size and style you know well, a comfortable A-line skirt, such as the Knee Length A-Line Skater Skirt, or a classic turtleneck can be a useful addition to her winter wardrobe. The same goes for a simple solid-color dress she can dress up or down.

Other easy wins:

• A soft scarf: it can be worn around the neck, as a headband or as a hair covering.
• Warm winter accessories such as a hat, gloves or a cozy scarf, which don't need to match a particular outfit.
• A long cardigan or duster in a neutral shade. It will usually be worn over other clothes, so don't size it too small.
• Jewelry that can liven up an outfit she already owns.
• Cozy pajamas or loungewear she will actually wear at home.
• A Kosher Casual gift card, when you are unsure of size or style.

Whatever you choose, keep the receipt. Just in case.

And don't forget yourself. If you've been meaning to replace a worn-out skirt or find a layering top that works with a favorite dress, the holidays are a good time to revisit your own wardrobe, too.

Shopping during Black Friday or Cyber Monday? Our online shopping guide covers budgeting, comparing offers and checking return policies before you buy.

Frequently asked questions

What should I wear to an office holiday party if I dress modestly?

Start with a work outfit and add one festive piece, such as a dressier top, a lace layer or jewelry. Layering pieces let you wear a party dress with the coverage you want.

What can I wear to a holiday party without buying a new outfit?

Start with a skirt or dress you already own. Change the look with a dressier top, cardigan, scarf or jewelry. A simple layering piece can also make a sleeveless or low-neckline dress work for your preferred coverage.

How can I make a dress with a low neckline work?

Add a neckline layer, such as a crew collar insert or a fitted shell underneath. It covers the neckline without the bulk of a second full top.

What skirt length works best when I will be sitting most of the evening?

Longer lengths are usually easier when seated, but it depends on the skirt and the seat. Try the sit-down check before you go.

What are good modest clothing gifts when I don't know someone's size?

Scarves, cardigans and gift cards are good starting points. If you're buying fitted clothing, check the recipient's measurements and the store's return policy first.

When is Hanukkah in 2026?

Hanukkah 2026 begins at sundown on Friday, December 4, and ends at nightfall on Saturday, December 12.

Sources

• U.S. Office of Personnel Management, Federal Holidays (Thanksgiving Day, November 26, 2026).
• Hebcal, Chanukah 2026 (begins sundown December 4, ends nightfall December 12, 2026).