Date Outfit Dilemmas & Dramas: Day Dates

I recall this one time I rushed to Target to frantically throw together an outfit for a date I had that night. I had “absolutely nothing” to wear, time was running out, and I was scrambling. THANKFULLY I found an amazing huge necklace (the kind that covers your chest, practically) that I threw together with my trusty black silk tank and a black pencil skirt with some heels, and called it good.

Nothing makes a girl more nervous than the feeling of not being put together all the way, or perhaps not being dressed properly for the occasion. I absolutely loathe not knowing what I’m getting myself into when it comes to situations that I need to dress for. For instance; wearing heels to a wedding only to find that it’s on a lawn. You’ve sunk 4 inches into the ground and have now become a permanent fixture in the garden and you wave disparagingly at guests, too afraid to uproot yourself for fear of uprooting clumps of sod with your pumps and receiving disapproving looks from the hostess. OR, you’re balanced so delicately on your toes as to NOT sink in that you’re gently swaying in the breeze, champagne in hand, and people have started to stare at your insinuated sauced ode to the garden fairies. So uncomfortable. (I’ve been there, this is real).

Here, to save the date dilemmas, I will create a style file that can practically cover any situation from day-time dates, evening dates, fancy soiree dates etc. so that you don’t have to have anxiety when the situations arise. Girl, I’ve got your back.

Day Dates are filled with uncertainty and unless your suitor has outlined the activities, you won’t quite know what you’re getting yourself in to. It could be puppies, a walk along the pier, lunch at the grove, a jaunt through the zoo, or a picnic in the park. You just don’t know. For a day date, you want to dress yourself in anticipation for fun to be had. If it’s a first date, you want your personality to shine, and not necessarily your outfit. Let it be demure and simple, but cute, so that the attention is on you, and not your neon yellow dress. Dress simply, but add your own personal touch with accessories that speak to your personality. Give your suitor a glimpse of who you really are.

Look One.

If you sense that your suitor may be posh and if you yourself are posh, or your situation might include having to be posh, then this look is for you. Based on your circumstance, the skirt might not work but the jeans definitely will. I kept it neat and tidy and added some fun bangles and a clutch so that you don’t have to feel like you’ve lost your fashion soul. The wedged sandals are perfect for just about any activity and the small heel will make them comfortable to wear all day. A sneaker wouldn’t be impressive enough, perhaps, and a heel would be too much. Throw a trench over your shoulders if there’s a chill breeze, and if the tank is a bit boob-y, exchange it for a simple loose-fitting black tee with a nice scoop neck. You don’t want to throw your body at your date, after all.

For hair, I’d do a nice loose top-knot or messy up-do. For makeup, you could keep everything really simple but add a nice red lip to spice it up, or just do natural makeup to show that even though you might be posh, you’re not high-maintenance.

Look Two

This look is perfect for any situation, any circumstance. It’s simple but cute, easy to wear and appropriate for a day date. I’ve kept it simple, again, by keeping the colors soft but adding a fun striped short. Wear the earrings and vintage sunnies for added style details and that minimalistic sandal for comfort and fun. A wedged sandal is my go-to for outings because they can be worn comfortably on grass, and they look dressier than a flat sandal. If the shorts won’t work for you (or its chilly outside) then try grey skinnies. The only time I love grey jeans is when you’re pairing it with colors that pop, like the cognac bucket bag and shoes. The bag is great alternative for a more undone day, and the denim jacket will pair nicely with the shorts and tank. Ta-da!

Notice that I’ve pulled some closet basics into each look as well, no need for a flashy outfit!

Let me know which looks you loved and how you could possibly mix and match them!

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