Words & Pictures

By Tracy Mitchell, founder and editor of Good Day Howard.

I hate first dates. But they are a necessary evil if you ever want to go on a second date (which is much better than a first date) and you get to dress up for them. I dress up because I like to feel ‘pretty’ on a first date — as opposed to ‘sexy,’ ‘cool,’ or ‘trendy.’

First I pick a lady-like dress in my favorite color and a dainty little clutch to carry. Then I find some good tall shoes to wear. I’m a tall lady (5’10″) so I always wear heels on a first date. I love my 4″ heels and I want to see a) if dude is still taller than me when I’m wearing them — super bonus points if he is, and b) if he’s not, his response to my being taller than him. (Hint: the correct answer is ‘Whoa, what a babe. I’m a lucky guy to be seen with such a foxy, tall lady.’)

Everything’s been going so well. It’s time to see just how good things are.

I honestly don’t have a clue what is ‘sexy’ to dudes, so I’ll just assume that see-through is good and pick something I think is pretty. Guys also probably don’t care about the ambience while you’re getting it on, but won’t you feel like a lovely lady with a nest of floral quilts and yummy-smelling candles?

You’ve been together long enough now that you spend time running errands together as much or more than you go out on ‘dates.’

Pick casual jeans (that make your ass look fantastic), a comfy tee and a ‘cool’ jacket, then girly it up a little with a big, chunky necklace, and some cute clogs.

Happy anniversary! For this occasion, dress up and show some respect to your relationship for making it a whole year together. Even if all you do is have a picnic in the park, step it up because this is special.

Just because you’re getting dressed up, doesn’t mean you can’t have a little fun. Pick a bright cocktail dress and then try not to match your accessories. Let them match in shape and fine-ness, but let’s color outside the lines, if you will. Hot pink goes really well with orange and aqua, don’t you think?

Now you’re living together, and it’s time to play hostess to all your mutual friends at your housewarming party.

Feel put-together and comfortable in a soft silk dress and your favorite flats. Let your necklaces and neon cuff make the outfit because you’ll be busy making mojitos.

Maybe at this point of the relationship you are both ready to tie the knot.

You can follow convention by wearing a beautiful white dress, but let’s mix things up a little with a blue bow headband instead of a traditional lace veil (because I’m pretty sure I’d have a nosebleed/panic attack under one of those things anyway) and some bright fuchsia party shoes for the feet.

More often than not, the relationship is actually going to end in a breakup. (This is statistics, not cynicism.)

If you are going to lie around on the couch for days on end (and you should), you are going to need some comfy pants to wear – the uglier the better since no one is going to see you wearing them because you are alone and you are going to be alone forever. (P.S. This is not true, but it is probably how you will feel.) Find a tee shirt with a slogan that empowers you. I like to get a really good wallow on, so I’ve picked the sloth as my spirit animal and I try to emulate him as best I can. Lastly, you’ll need a pretty tumbler in which to pour your bourbon. Because you are a lady.

Tracy Mitchell is the founder of and brains behind the fashion and lifestyle blog, Good Day Howard. A personal stylist and a wardrobe coordinator living in Sacramento, Ca, Tracy spends her time treasure hunting, eating, instagramming, talking, making her home look more like an antique store, reading about food and boho artists, tweet tweet tweeting, singing in her car, blogging, and cuddling with her kitty, Wednesday. She’s also a super rock star for guest blogging for her friend, Nora, while Nora moves across the country (again.)