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5 Cute Outfit Ideas for Your Holiday Season Events

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Woman holding a christmas present

With its hot chocolate and cookies, winter break also brings us plethora of events that each come with their own fashion needs. It is, after all, the season of togetherness–we’re all going to be spending time with our friends and families and want to look fabulous while doing so!

Here are five outfit ideas for common events you might be attending over winter break!

Ugly Sweater Party

It’s pretty much inevitable that you’ll be invited to an ugly sweater party (AKA a “Tacky Christmas Sweater Party”) sometime this winter break. Obviously, the whole point of the party is to showcase a totally tacky sweater, but that doesn’t mean the rest of your outfit has to be ugly!

If you have an ugly sweater party to go to, try wearing your sweater with a cute pair of leggings and boots, grey jeans, or even a skirt with a pair of printed tights. You’ll fulfill the theme requirement, but still look totally cute. If you’re looking for a place to buy ugly sweaters specifically for your party, thrift stores are a great bet! Ragstock stores also carry a special selection of these tacky treasures on the cheap this time of year.

What to Wear to an Ugly Sweater Party

Ugly Sweater

Product Information: Oversized Ugly Sweater, uglysweaterstore.com. Mini Christmas Tree Earrings, punkypins.co.uk. Aerie Cable Slipper Sock, American Eagle. Ruffle Top Slub Top,Forever 21. Seamless Legging, Wet Seal.

Dinner with the Boyfriend’s Parents

If you’re dating someone, the holidays are usually a time when you’ll be spending a bit of time with your significant other’s family. While you want to showcase your style and look great, these occasions usually call for outfits that are a bit more conservative or dressy than what you’d usually wear, especially if you’re meeting the parents for the first time!

A good tip is to dress how you would for a religious ceremony–respectful, but fashionable. Nothing crazy, not too much skin, and nothing extremely tight. You want to show these people what a classy girl you are! Highlight your style with pieces with an interesting, eye-catching additions. If the dress below is too over-the-top for you, just substitute your favorite long-sleeved frock or pair a short-sleeved dress with a cardigan.

What to Wear to Dinner with the Boyfriend’s Parents

What to wear to meet your boyfriend's parents

Product Information: Lace Inset Tunic Dress, Top Shop. Denier Opaque Black Tights, ASOS. Ach Ach Liebling jewelry Crest Earrings, moxsie.com. Fabulous Platform Shoe Boot, Priceless Shoes.

Meeting with Friends from High School

Whether it’s at an official reunion or at an alumni holiday party, you’ll probably be meeting up with a bunch of people you used to go to school with. Since they haven’t seen you in a while, you have the perfect opportunity to impress them with your new college attitude and style! Just because you used to wear graphic tees and flared, distressed jeans, doesn’t mean you have to now! Use the occasion to wear something fun, new, and unique. It’ll give you something to talk about!

What to Wear When Meeting with Friends from High School

What to wear when meeting up with friends from high school

Product Information: Current/Elliot The Skinny Studded Jeans, Net-a-Porter.com. House of Harlow 1960 Gold Starbust Cocktail Ring with Black Leather, Singer22.com. Metallic Thread Knit Tunic, Forever 21. Suede Python Reva Ballerina Flat, Tory Burch.

Christmas Morning

If you celebrate Christmas, you know that Christmas morning can be one of the best days of winter break. If your family is anything like mine, Christmas morning usually includes waking up early, eating breakfast as a family, and opening all of our presents. Also, it normally involves taking lots of pictures – so you don’t want to wear ratty old pants and an oversized tee!

Christmas morning is a great time to wear your favorite thermal tops, festive pajamas, and comfy slippers. It’s cozy and traditional–something that totally brings back childhood memories!

What to Wear on Christmas Morning

What to wear on Xmas Morning

Product Information: Jaden Pajama Pants, Abercrombie & Fitch. Women’s Aerie Robe, American Eagle. Full Tilt Womens Boy Tank, Tilly’s. Ugg Australia Sweater Knit Scuffette Slipper, Nordstrom.

New Years Eve

If you’re a glamour girl, you probably love NYE. It’s a night where anything goes, from feathers to sequins to crazy bright colors, New Years Eve is all about making a serious impression with your style. Attention-grabbing skirts and dresses are par for the course, but that doesn’t mean that you can’t rock a hot pair of jeans, leggings, or this season’s trendy jumpsuit. Grab something you can dance in and put on the glitz: it’s time to channel your inner glamazon!

What to Wear on New Year’s Eve

What to wear on New Year's Eve

Product Information: Animal Tube Skirt, Newlook.co.uk. Croco Embossed Origami Top, Forever 21. Multi Layered Chain Necklace, Arden B. Women’s Mossimo Supply Co. Odell Ballet Flats,Target.

Your thoughts?

What are you all wearing for the holiday events in your lives? Is there anything you go to or do every year that I missed? Let me know in the comments section!

* Top image ©iStockphoto.com/Choreograph

Posted on on December 15, 2009 / Filed Under: Fashion Tips / Tags: , , , , , , ,

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23 Responses to “5 Cute Outfit Ideas for Your Holiday Season Events”

  1. 1
    December 15th, 2009 at 5:37 pm

    I love ugly sweater parties!!! They’re so silly and fun. Glad you put that in the post.
    And that forever 21 tunic in the outfit for meeting with high school friends is now on my gift list. It’s really cute.

  2. 2
    December 15th, 2009 at 7:12 pm

    I love these! Thank you!

  3. 3
    December 15th, 2009 at 7:45 pm

    Could you please prescribe something dressier for New Years. I’m having a major dilemma over what kind of outerwear to wear to a formal event over my dress. My boyfriends mom is wearing a fur coat and it is a black tie event. I have no idea what to wear that I can afford.

  4. 4
    December 15th, 2009 at 7:46 pm

    I love these! Amazing post!

  5. 5
    December 15th, 2009 at 8:54 pm

    I am so having an ugly sweater party now, what a fantastic idea! I must say though, that dress for meeting the boyfriend’s parents would not be something I would try to wear, its a little dowdy.

  6. 6
    December 15th, 2009 at 9:39 pm

    This is a very very helpful and pretty post. I just had an ugly sweater party and I had no idea to find anything that goes with that sweater to make it look cuter and more up-to-date. I think you should have another post that shows us how to do the make up with each outfit though. A pretty face also boost up the outfit a lot.

    Over all, love this post! <3

  7. 7
    December 15th, 2009 at 10:27 pm

    I actually have a huge love for tacky sweaters! The uglier and tackier, the better! lol It’s a guilty pleasure…

    I am also in LOVE with the “dinner with boyfriend’s parents” outfit and the “christmas morning” outfit! So adorable!!! I like looking put together and cute during the day, but I also like to look cute when I’m relaxing at home and I love nice pajamas!

    Great post :)

  8. 8
    December 15th, 2009 at 11:23 pm

    i love love love this post, esp christmas morning and dinner with boyfriends parents

  9. 9
    December 16th, 2009 at 12:33 am

    These outfits are awesome!
    Although, I wouldn’t wear the last one, too glamazon for me. And hey! That tacky sweater is cute, I don’t think it’s ugly at all! A little cutesy, maybe, but not ugly. Trust me, I know ugly Christmas sweaters, and I’m glad you picked one less on the hideous side and more on the trendy side. I’ve never heard of Ugly Sweater Parties, do those really exist?! That’s hilarious.

  10. 10
    December 16th, 2009 at 12:53 am

    Products Shop, you look good. I love this fashion style

  11. 11
    December 16th, 2009 at 1:56 am

    I got invited to an ugly sweater party this Saturday. This post, just in time :D thumbs up.

  12. 12
    December 16th, 2009 at 1:59 am

    This article is just what I needed. Thanks! Some really cute outfits and it is nice to have some guidelines for different occasians.

  13. 13
    December 16th, 2009 at 2:01 am

    I love this post! I’m definitely going to be spending a TON of time with the boyfriend’s parents, and the New Years posts really got me thinking about what I want to wear for New Years!

    Could you maybe do a post on Holiday hairstyles?

  14. 14
    December 16th, 2009 at 3:23 am

    I agree with Michelle! A post on holiday hairstyles and make-up would be great! :)

    Great post I’m loving all of these outfits especially the dinner with the boyfriends parents.

  15. 15
    December 16th, 2009 at 6:16 am

    “If the dress below is to over-the-top for you, just substitute your favorite long-sleeved frock or pair a short-sleeved dress with a cardigan.”

    I think it’s supposed to be “too,” not ‘”to.” Just throwing it out there. Great post!

  16. 16
    December 16th, 2009 at 10:27 am

    I really, really love the outfit for having dinner with your boyfriends parents–very stylish yet classy. I was waiting for someone to post outfit ideas on this subject, because I am always so freaked out about what to wear to my boyfriend’s family functions (even though we’ve been together over 3 years now…)! However, I am on an extremely tight budget and as much as I love the lace TopShop tunic, its a bit out of my price range. Any chance you could throw out some other dress/tunic outfit ideas for dinner with the bf’s family where the dress part of the outfit is say about $50 or under?

  17. 17
    June 9th, 2011 at 10:33 pm

    the 2nd and 3rd ones are sooo adorable i love the shoes on the 2nd one and the shirt on the 3rd oooh i want them i am in <3

  18. 18
    December 9th, 2011 at 3:06 pm

    This is so cute! and its exactly what macbarbie07 did in her most recent video

  19. 19
    December 9th, 2011 at 4:09 pm

    Macbarbie07 from YouTube copied this entire thing on one of her most recent videos. I was like hey that’s really familiar!!

  20. 20
    December 14th, 2011 at 3:18 am

    I love all of these outfits! *Goes out to buy the New year’s set* =)

  21. 21
    December 28th, 2011 at 12:57 pm

    macbarbie07 on youtube copied you :/

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