First Date Fashion

Whether it’s a first date or the tenth one, picking an outfit is sometimes the most difficult part and I never seem to have the right mix of casual but sexy cool outfits!

If you’re anything like me, you have a closet half full of “cute tops” you grabbed last minute for a hot date that you’ve worn maybe once or twice.

**I think you should wear what makes you feel sexy but comfortable. There’s no point in trying to look like anyone other than yourself. If your date doesn’t like it, they can shove it. (Or, you know, you’re not a good fit.) It will only cause problems down the road if you put on a show.

I’m no fashionista and in all honesty, I think you should wear whatever the eff you want and be yourself but if you’re looking for a few suggestions, I’ve put together a few ideas.


Sporting Events:

Sporting events are awesome and plentiful in Toronto. Our fans are committed and rowdy. Whether you’re going to see the Jays or the Argos, or headed to a TFC game, it’s going to be light hearted and fun. It’s a great first date in my opinion. There’s the opportunity to talk and flirt, but also the safety net of the game if your date isn’t so chatty. (or not your type)

I try to stick with something cute and sporty. I have a pair of white Puma ballet flats that usually do the trick for standing for long periods of time. I think converse or keds would be a cute alternative. I’m a jeans and t-shirt kind of girl when I’m off the clock so this is my element.

Oh, and dress in layers if you’re going to be outside at night (cool breeze off the water for TFC games or the dome could be open for the Jays) AND, top it off with a team baseball cap for a winning look. (see what I did there?!)

Active Date:

I have yet to figure this look out. I have a potential active date coming up, a bike ride, so I searched bike fashion on Pinterest. Why all the skirts?! I’m not a seasoned biker so I’m thinking I will stick with something like this…

Coffee:

I feel like coffee dates for first dates are becoming the norm, especially for online dating. It’s kind of like the pre-date date to determine if you want to go on a real first date. Sometimes it’s the prelude to dinner or another activity but it’s also a buffer so you can get out if it’s not a good match.

I try to keep my coffee date looks casual and rarely do activities after (save the real first date for another night) Again, I’m all for jeans and a cute top or blouse. I have a favourite pair of Levi’s boyfriend jeans from a bazillion years ago that are my go to.

After Work Drinks:

This one is tricky because you have to look good ALL DAMN DAY. (not my forte) And this look only works if your day job includes working at a stuffy office like moi.

Hint: bring deodorant, your toothbrush and toothpaste, and your make-up to touch up post work before heading out for this date.

I usually opt for a pencil skirt and blouse with heels. A slouchy belted shirtdress, à la numero 3 (pictured below), is another great option and allows some eating room. Pencil skirts don’t hide much of the lower belly pooch if you know what I mean.

Dinner:

My go to outfit for dinner dates as of late has been this Joe Fresh dress in white and navy (pictured in the centre below) with a jean jacket and depending on the boy in question, wedges or sandals.

Okcupid and POF let you know a guys height, and me being 5’4″, more often than not I can wear heels. With Tinder, unless they’ve listed it in their blurb, I play it safe in flats. If you don’t give a sh*t, wear whatever you want!!

The following are other great options. If I know I’m going to be eating, I tend to opt for a shift dress to hide my food baby like the first two options below. (Eating seems to be a real concern for me) The best part about dresses, is you can throw on heels if you’re going somewhere a little fancier, or flats for some casual sushi. Mmmm….sushi.

Do you have another type of date you need help with an outfit for?? Let me know in the comments and we’ll help you out!

– A

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