So you’re neck deep in the whole internet dating game (I assume, since you’re here and all) so clearly, you’re a practical, efficient woman who wants to do everything at the top of her game. With all of the wondering about which decisions to make for your career, where to live, who to date and which exercise fad will keep you looking fab, there isn’t a whole lot of time to ponder life’s really important detail questions…until they’re staring you in the face.
One such category of question is the omnipresent “what to wear” dilemma. From day to day, making this choice might come naturally. You’re going to work: done. You’re going to the dog park: easy. Grocery store: piece of cake. But as many times as it’s easy to know what to pull from your wardrobe, there are at least as many when dressing can be quite the conundrum. Not to worry. I’ve done the legwork for you. And by “legwork”, I obviously mean, “I’ve dressed horribly inappropriately for just about everything”. Here are a few things I’ve learned:
Situation: Day one post-breakup
What to Wear: Granted, my typical breakup attire consists of a box of tissues, a ratty t-shirt and a bottle of vodka. I wouldn’t call this the healthiest approach to grieving but it is a pretty good start. Add these things: a shower (you feel better if you’re clean, always) and pants (something comfortable but that you still look good in. same goes for the aforementioned ratty t-shirt). If you look icky, you’ll be less inclined to let your friends come visit, which will make you feel better than you think.
Situation: First date
What to Wear: The fun part about online dating is the thrill of the first date. Those beginning moments when the cyber-communication gives way to real face time are exciting and unforgettable so naturally, you want to look equally exciting and unforgettable. The key is to not overdo it. If all goes well, you’ll be seeing this person again, right?
My strategy is to wear my second favorite outfit on the first date. That way, you still look amazing and confident but you then you get to blow away your new flirty friend even more the next time you guys hang out when you wear your total knock-out favorite look.
Situation: Job Interview
What to Wear: Whoever said “dress for the job you want, not the job you have” really should’ve said something regarding how to dress for the job you’re currently trying to get. Here’s my advice: style yourself just one level above the job you’re interviewing for. For example, if you’re vying for a job where you know you’ll be able to get away with jeans, opt for nice slacks or a skirt.
Whatever you choose, make sure it is flattering: not too sexy, not too dowdy, fits like a dream and makes you appear put together without being too flashy and distracting. You want your interviewer to be focusing on your amazing resume, not your amazing cleavage.
Situation: Meeting your new beau’s parents
What to Wear: Okay, I’ve made a few mistakes in this department before. With all the nervousness and the involvement of the person you’re dating, it’s easy to automatically dress like you’re going on a date. Depending on how you typically dress for dates, this might be okay. Not if you’re me and that includes a short skirt and CFM boots. You also don’t want to go too far in the other direction and dress like a matronly mom.
This will backfire for two reasons: 1) once your man sees you (looking like a mom) and his mom in the same room, he’ll get a bad case of the panics. 2) contrary to common belief, parents usually want their sons dating dynamic, interesting people…not prematurely-old women. If you want your fellow and his folks to start seeing you as part of the family, try to act like it but with a fine polish in the beginning.
Dress like you would if you were going to see your own parents but the nicest version of that. If you would throw on jeans and a tee to see your family, put on your best pair of blues and a nice (but not shiny. Never shiny.) top. Keep the shoes modest.
