Unabashedly¬†Halloween is my favorite holiday. If it was socially acceptable I would still put on a costume and trick or treat, eat copious amounts of candy, and watch the ABC Family classic movie “Halloweentown” every day for two weeks straight. But since that isn’t exactly in the cards for me anymore (besides the candy part), I love to focus on putting together the perfect Halloween costume that is the ideal mix of fun, figure flattering, and ideally one that can be recreated with items already in my closet.

1) Pumpkin Princess: I love the idea of being a “princess” on Halloween and this pumpkin version would be a fun twist on a classic. While the dress in this picture is a little too short for my liking, I could see wearing a basic orange dress, sewing on a few pieces of felt for the pumpkin face, and throwing on some polka dot tights to keep covered and warm.

2) Hockey Star: This dress would be so cute for anyone with a larger bottom half. The shortness of the dress (worn with leggings or tights underneath) shows the perfect amount of leg while remaining tight in all of the right areas. The sleeves add a bit of warmth and I love the idea of wearing tube socks and tennis shoes to be comfortable all night.

3) Chic Sailor: Pants! Yes! As someone that already owns blue and white pants, this outfit wouldn’t be too hard to recreate. I’d love to invest in a pair of fantastic red pumps to really round out the ensemble.

4) Native American Diva: Fringe is a bit harder to make on my own. But this costume is so cute I would almost consider buying it. With my favorite Winter boots worn on my feet, patterned tights and a camisole underneath, i’d be so happy to wear this adorable costume.

5) Raccoon Fairy: I love the idea of a hood for Halloween. It always makes me feel moody and mysterious and with fun patterned knee high socks to keep covered and some fun feathers added to a black dress, the costume is kept from feeling too creepy.

A few more i’m loving:

Regardless of the outfit I end up choosing, there are a few key tips I always keep in mind when dressing for the occasion:

-Can the outfit be worn with tights/leggings? Tights always make me feel pulled together and not like i’m flopping around all night. Plus they add a bit of extra coverage and warmth if you will be outside at all.

-Does the outfit require a high heel? While heels are fun for certain occassions, my Halloweens always involve a lot of walking. So I tend to look for costumes that can be worn with a boot or fun wedge to keep spirits up and my feet from dying throughout the night

-Is the costume figure flattering? While some women see Halloween as an excuse to dress outlandishly, I don’t see it as a reason not to look your best. I like my costumes to show off my best assets, be fitted in the right places and looser in my problem areas. For me personally, a costume that is tighter around my midsection but looser in the bottom half makes me feel the most comfortable.

*all images via Spirit Halloween