9 Holiday Outfits for Every Festive Occasion

‘Tis the season for holiday gatherings. ‘Tis not the the season for long, agonizing stares into the depths of your closet, with the contents of your dresser drawers surrounding you in small heaps as you try to determine what to wear.

With a little bit of proper planning and ingenuity, dressing for the occasion won’t have to take endless hours. Debating whether someone will remember if you wore the same dress to a party last year, sorting out the perfect outfit for the office party on Thursday, drinks with friends on Saturday, and Sunday dinner with the family just got a lot easier with this holiday outfit guide.

Keep the focus on style, cuts, and colors, not necessarily exact pieces, and you’ll find the style inspiration needed to have you dazzling at every occasion this year.

Source: hm.com, limited.com, dsw.com, jcrew.com, sperrytopsider.com

Source: hm.com, limited.com, dsw.com, jcrew.com, sperrytopsider.com

1. At “Friends-giving”

Just because you’re choosing comfort doesn’t mean you have to choose sweatpants. Keep your look casual as you gather with friends to celebrate what you’re thankful for. Riding boots and a scarf or cuffed jeans and boat shoes will keep you fashionably in season. A scarf adds warmth and a pop of color to any neutrally toned outfit. An envelope clutch keeps the casual feeling going — plus, you’re hanging out with friends and eating, so why tote around a huge bag?

Above: H&M Fine Knit SweaterLimited Cuffed Slim Boyfriend JeansSperry Audrey Slip-On Boat ShoeJ. Crew Plaid Wool ScarfBCBGeneration Envelope ClutchBandolino Calliope Riding Boot

Source: keds.com; modcloth.com

Source: keds.com, modcloth.com

2. Pre-Thanksgiving with a sporting clan

If your family is Kennedy-esque in its appreciation for tossing around the pigskin, you’ll want an outfit that lets you play to your heart’s content. Pick a sweatshirt or pullover that keeps you warm but won’t restrict your arms. Throw on a pair of broken-in boyfriend jeans and lace up your sneakers: It’s game time.

Above: Boyfriend jeansKedsWe’re Young at Heart Sweater

Source: hm.com, asos.com

Source: hm.com, asos.com

3. Thanksgiving when you’re the cook

The last thing you want is your outfit ruined by a splattering sauce or a spilled ingredient. If you don’t have time to change before guests start arriving, try a simple sweater-dress and tights. Stay away from baggy clothing that can be dragged through food and from anything too heavy — it will be warm in the kitchen with the oven going all day.

For the consistently messy, an apron may be in order.

Above: H&M Fine Knit DressASOS Knitted Dress with Slash Neck and Belt

Source: http://bananarepublic.gap.com/

Source: bananarepublic.gap.com

4. Casual Thanksgiving

Falling somewhere between a step up from jeans but not as dressy as a skirt — depending on how you style them — are slim-fit ankle pants. With multiple stores carrying them in a number of colors and prints, there’s bound to be one pair that suits your personal preferences. Plus, they can be worn with almost anything, from boots to flats, t-shirts to sweaters. Riding boots will give the pants a more casual look, as will simple sweaters and knit shirts. If you want to be a tinge more dressy but still casual, try a heel and sweater combination, or a blouse with your boots.

Above: Banana Republic Sloan Pant

bananarepublic.com, lordandtaylor.com/, dsw.com, shop.nordstrom.com, modcloth.com

Source: bananarepublic.com, lordandtaylor.com, dsw.com, shop.nordstrom.com, modcloth.com

5. Holiday caroling

When it comes to caroling, it’s all about outerwear and accessories. Going door to door and singing Christmas songs is the perfect time to show off a new coat, because when else will you have the chance to wear heavy wool items for extended periods of time? Make a statement with a bold print or color. If your adorably cut coat is in a shade like grey or black, amp it up with accessories like hats and gloves that will also keep you warm. Walking through the neighborhood is hardly the time to bust out your high-heeled shoes, but a riding boot with a low heel or no heel at all will be warm, practical, and stylish.

Above: Banana Republic Grey Fit and Flare Bow CoatGUESS Wool Walker CoatGUESS Plaid Fit & Flare JacketCable Knit Head WrapLauren Ralph Lauren Tartan Military Tech GlovesKelly and Katie Turner Riding BootFestooned as Possible Hair Clip Set

Source: http://www.lordandtaylor.com/

Source: lordandtaylor.com

6. The family party

Dressing for Great Aunt Gertrude’s sense of what is proper doesn’t mean you have to covered from head to toe at the family party this year. The fit-and-flare design of this dress gives it a playful feel while still being completely family appropriate. Opting for a print and a bright pattern is a great selection for a party, and if you’re dashing out to meet friends, a quick change of jewelry, hair, or shoes can take this style across several situations.

Above: Eliza J Sleeveless Floral Fit and Flare Dress

Source: http://us.asos.com/

Source: us.asos.com

7. Afterhours with the office

If your holiday office party starts right after work (and even if it doesn’t), this high-waisted skirt should be your go-to when it comes to socializing with coworkers this season. The bold pattern makes enough of a statement on its own without being overly pushy. Pairing it with a simple black turtleneck, like the one shown above, balances the work-party dichotomy that can be so difficult to nail down.

Above: ASOS Warehouse Gold Jacquard Skirt

Source: katespade.com, bananarepublic.com, hm.com, whitehouseblackmarket.com, urbanoutfitters.com, asos.com

Source: katespade.com, bananarepublic.com, hm.com, whitehouseblackmarket.com, urbanoutfitters.com, asos.com

8. When you have dress déjà vu

Worried someone will realize you wore the exact same black dress to last year’s party? Recycling the same dress is the perfect time to make it a canvas for something else, like a great piece of jewelry or a bright handbag. This will work especially well with neutral dresses, such as solid colors or limited patterns. If you aren’t a fan of sparkly clothing, old outfits are a great opportunity for shiny accessories. Sequin heels will be eye catchers, and everyone will be so busy with your shoes that they won’t remember you’ve worn the outfit before.

Above: Deepa Gurnani Gold Statement HeadwrapMixed Metalic Sequin Low Heel PumpTai Box ClutchH&M Bead NecklaceKate Spade Shaken and Stirred Statement NecklaceASOS Vintage Style Pearl Ring

Source: http://www.lillypulitzer.com/, http://www.asos.com/, http://www.net-a-porter.com/, http://www.whitehouseblackmarket.com/

Source: asos.com, lillypulitzer.com, net-a-porter.com, whitehouseblackmarket.com

9. On New Year’s Eve

Proving that rules are made to be broken, white is white hot this winter, extending well beyond its Labor Day expiration date. Stand out from the sea of little black dresses on New Year’s Eve with white. If breaking the rules isn’t your thing, you can still distance yourself from the pack and shimmer the night away in metallics.

Above: ASOS Baroque Embellished DressLilly Pulitzer Wythe DressT By Alexander WangMixed Metallic Sequin Party Dress

Don’t Miss: 5 Healthy Thanksgiving Dishes with Classic Roots.