For many moons I was ashamed of being called a girly-girl. I wanted to be athletic and cool like those girls who pulled off a ponytail everyday, and were proud to call themselves tom boys. Alas, I thoroughly enjoyed playing with Barbies and Polly Pockets. In high school, I did everything I could to get out of gym, and I wore makeup every single day. It wasn’t until about two years ago that I actually embraced my chronic femininity, when this super sporty girl was going on about the fact that I was wearing a dress just for hanging out with friends over some beers. She went on to say that she only wears dresses on very special occasions and can’t wait to get home and rip it off. Out of nowhere I blurted out: “if I could wear a dress everyday, I would.” No one said a word, even I was shocked by my confession. Then I realized, it was true.

Sure, I love a great pair of fitted jeans, and I look forward to sweatpants as much as the next girl, but I absolutely adore dresses, and am surprisingly comfortable in them. So I was thinking that one could feasibly wear a dress everyday, be stylish and comfortable, and actually save money. All you need is 10 basic dresses, and you can just accessorize from there.

Begin with the 10 categories below. Try to fit the dress choice within each, but stick to the more casual end over formal, it’s easier to mix and match this way. Set the budget at an average of $50 per dress, considering that some may be more and some less. Each can be used within its own category, or you can mix them up using accessories. Of course, you may not want to buy everything at once, this is a process, a challenge – a challenge with a very nice reward: a whole new wardrobe made up entirely of dresses!

1.

The Dresses

. . .

The Little Black Dress

Let’s begin with the obvious. Mostly making appearances at cocktail parties, banquets, work parties, or really anywhere – the little black dress is classic. This dress should be tasteful and sexy. Consider going with 3/4 inch sleeves, this way you can pull it off anytime of year with less help from accessories. Never go with a super low neckline, you want to keep it simple and something that will be appropriate for any occasion.

The Pastel Event Dress

This is the dress you wear to a wedding, or on Easter Sunday. It can also be a great choice for a fancy lunch out with the girls or even a business professional. The best color here would obviously be beige. You may also want to stick to knee length since this will mostly be worn during the day.

The Holiday Dress

For this to work for more than one occasion, I recommend going silver or gold over red or green. Silver preferably, it can work for New Year’s Eve bashes, and you can accessorize with reds for Christmas/Holiday parties.

The Showstopper

This should end up being the most formal of all the dresses. Think flaired skirts, interesting necklines, and freedom in choosing the color that really works for you. The showstopper won’t make as many appearances, but when it does it needs to work every time. Put a lot of thought into this dress.

Big Presentation Professional

This is not something you’re going to wear to the office everyday. You will wear this for that ‘big presentation,’ or to an upscale networking event. Go for clean lines, and choose something that will fit well with a prep school blazer.

Business Casual

We’re getting into the more casual attire. While all of these dresses can be used in other categories, this and the following four are super versatile. The business casual dress is something that can really be worn everyday at work, to meetings, and business lunches. I would go with short sleeves over long or 3/4 inch, since you will probably be pairing this with a blazer or cardigan.

Summer Casual

The summer casual dress should be something that can be worn with summer boots or flip flops, on the beach or to a music festival. Keep it simple. Think: clean, free, Hamptons beach house. This would probably be the only dress where I would say you could pull off white, for our purposes anyway. Also consider: brown, beige, pale pink or green and even navy blue.

Winter Casual

Have more fun with color here, and go for a 3/4 inch sleeve. I’m really in to peach right now for winter. It looks beautiful with grays, blues, browns, and even purple. Just keep in mind the obvious accessories that will go with this: scarves, boots, hats, coats, etc.

Spring Casual

Pretty much anything goes; this is the dress that can be a bright color, because we can always tone it down later. This may also have a shorter skirt, and an interesting neckline, or something that ties up in the back.

Fall Casual

This is my favorite season, and my favorite colors. Dark versions of any color really can work here. I recommend 3/4 inch sleeves, short skirt length is fine since you can pair with leggings and boots, and choose thinner material so you can match with blazer or cardigan without being uncomfortable.

2.

The Accessories (head to toe)

. . .

Accessories are important because it can help to change the occasion and even the style of the outfit. Some of these are obvious and are completely unique to you, it’s the fun part. Some of these we don’t all have in our wardrobe, but maybe we should start taking advantage of them. I am mainly talking about blazers and bustiers. First of all, blazers help to give any outfit a more professional or upscale look, it’s not as lax as a cardigan. Since you will be wearing assorted dresses, bustiers help to give the outfit a more tailored look, and helps to accentuate those curves.

Hats, clips, and headbands