Holiday outfits for every occasion + gift ideas!

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Holiday outfit with red plaid top, black jeans, and black pointed toe flats

The hustle and bustle of the holiday season is almost upon us. While, great the end of the year brings so much to plan for: gifts, get together, and what you are going to wear. I’ve got your holiday outfits covered so you’ll have one less thing to worry about this season!

I want this post to be a comprehensive guide to dressing for the holiday season. Under each category you’ll see an outfit collage. This is the base outfit idea, but I’ll also share other items you can shop for a similar feel. In some of the categories I’ve also included items that I think could make great gifts, so it’s kind of like a two for one!

This post contains affiliate links. So if you make a purchase using my link, I’ll receive a small commission at no additional cost to you.

Outfit details above: Top | Jeans | Shoes – Heeled version | Similar Flats

Traveling for the Holidays

A holiday travel outfit featuring a sweater, wrap, jeans, sneakers, and monogrammed suitcase.

Let’s talk holiday travel. Many of us have somewhere to go for thanksgiving, Christmas, or both. When traveling comfort is key, but if you’re like me you still probably want to look stylish.

Whether you are traveling by car or plane, stay warm and comfortable with this look. A super cozy sweater is stylish and comfy, and add a wrap that can double as a little blanket. Slip on shoes keep going through security easy if you are traveling by plane.

I always like to wear jeans while traveling on a plane, because of their bulkiness, I prefer not to pack them. If you like wearing leggings while you travel, you can easily swap them for the jeans.

Travel Gifts

I love this suitcase because you can personalize it! It would also make a fantastic gift for a frequent traveler. If you don’t want to splurge on something that big, opt for a personalized jewelry organizer or nice cosmetic bags. I added the books if you need some travel reading, or as another gift option.

4 books to read this fall.

Thanksgiving Outfit

Thanksgiving outfit idea with a sweater, tweed skirt, boots, and a hair bow

I decided to make this Thanksgiving outfit a very fall color palette. Wearing burgundy and cranberry tones just feel so Thanksgiving! This outfit balances casual and dressy, so will work well for a variety of functions.

The knee high riding boots help give more coverage and warmth with the shorter skirt. I think this outfit would also be cute with black tights if you want an extra layer.

Casual Holiday Look

Casual outfit for the holiday season with a sweatshirt, jeans, boots, and beanie

Around where I live we have a few outdoor light displays that you can walk around. That was my main inspiration for this holiday outfit. The idea is to be comfortable and warm while still looking cute. I also think this would be a good choice for Christmas shopping as you wouldn’t need to carry your coat (unless it’s really freezing!).

A belt bag keeps everything you need at your fingertips and lug sole boots provide stability if you’re walking a lot. I just purchased this sweatshirt. I love that it gives a holiday look without actually being a Christmas sweatshirt.

Dressy Holiday Outfit

Dressy holiday party outfit with plaid dress, black bag, black pumps, and pearl jewelry

In contrast to the last look, this look is for holiday parties, or work events, where you need to be dressed up but still want a holiday feel.

This tartan dress, with the ruffle trim and midi length, is perfect for fancier holiday occasions. Make it even more special with pretty jewelry and a nice pair of heels.

Hostess Gifts

If you are attending a great party, don’t forget a hostess gift! Grab something for the home, or something they can use for their next party.

Cozy at home

Cozy pajamas and slippers and pampering gifts

Whether you’re spending Christmas morning in PJs unwrapping gifts, or just want some festival loungewear, there are so many options for looking cute and cozy at home this season.

These pajamas are made from pima cotton, so they’re extra soft. Add cute slippers to complete your look. And don’t forget the hot chocolate!

Seasonal self care

Self care is easy to forget about, especially during busy times. Pamper a family member or friend (or yourself!) with some of these little luxuries.


I hope you found this post helpful for planning your holiday outfits, and maybe you found a gift idea too! Check back soon. I’ll be sharing all things grandmillennial for the holidays!

winter to spring transition outfit with a striped sweater and medium wash jeans

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