For the funeral, I opted for another black dress (Kookai), but this time I paired my tent dress with tights, heels and gloves. Just because it's a funeral doesn’t mean you have to look boring, but covering up and remaining modest is the number one thing to consider.

As we Milwaukee fashionistas rev up for the holiday season, it is important to have a dressing plan for the different parties and events we may be required to attend. There are endless engagements, which mandate a different style of dress, and your little black dress might not be appropriate for each obligation.

Having recently attended an anniversary dinner as well as a funeral, it was clear that the same black dress would not suffice for the two occasions. Additionally, I have a slew of weddings, parties and fashion shows to throw into the mix.

As I generally pick basic black for my color palate, it is important to stand out when necessary, as well as blend in when it's someone else’s show.

For my anniversary dinner, the show was definitely all mine (and my boyfriend’s), so I felt shining was not out of the question. However, our restaurant of choice, Bacchus, did not call for a loud party dress.

The problem was solved by wearing a one-shoulder black dress with ruffle trim (3.1 Philip Lim, Neiman Marcus) and gold flats (Chanel). This way, I stood out with a unique dress, but did not look overdressed because of the flats.

For the funeral, I opted for another black dress (Kookai), but this time I paired my tent dress with tights, heels and gloves. Just because it's a funeral doesn’t mean you have to look boring, but covering up and remaining modest is the number one thing to consider.

While funerals generally have a sad aura surrounding them, they should be a celebration of life; so do not dress frumpy and add to the sad cloud hovering over the service.

My next engagement is a friend’s wedding. For weddings, it is especially important not to stand out too much and take the attention away from the bride. (Come on, we all know this!)

Whether I am dressing myself, or helping others pick out an outfit at Lela, I generally steer away from white or anything too flashy (sequins, too low cut, too much pattern). While the reception may turn into a party, it is not your party!

Because this is a friend’s wedding, I want to wear a fun dress, which is somewhat understated. I am planning to wear my anniversary dress again, only this time sporting comfortable heels (Steve Madden, Macy’s) that I’ll be able to stand on all night long (and ones I will not mind getting spilled on).

I know it will be a rowdy group, and shoes are usually the first part of my outfit to get spilled/stepped on. Because black can get boring, I will wear a bright yellow clutch (Lauren Merkin, Hers) to spice it up.

Hopefully my dressing plan will help clear up questions on how to dress for the holiday season.

Usually, one or two dresses can carry you through, but switch things up with a variety of shoes and clutches; those elements can totally change the look of a dress.

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