Date Nights & What to Wear

Dating is one of the most complicated social interactions sometimes, especially when it comes to first dates or dating someone you’re still getting to know. Why is it so complicated? Because deciding on an outfit can take FOREVER. At least it does for me.

I’m a planner. I like to plan my outfits for the occasion. And I usually plan my outfits the night before, even on regular days when all I’m planning for is based on the weather and if I’m going to school or work.

Either way, planning a date night outfit is never a stress-free occasion for me, however I’ve helped a number of friends with all different style types dress for dates. And so, I hope I can help you out on your next date with some style ideas.

Day dates are a lot easier to style for. You can dress super comfortably, but still dress up and not have to worry about looking “overdressed”. I put that word in scare-quotes, because overdressing is subjective to your and others’ opinions.

Date nights are the trickier ones to dress for. You want to make a statement, but you do want to look and feel comfortable.

Key word in either situation is comfort. So lets break it down into styles.

Lipstick femmes, or those whose styles are most commonly described as “sophisticated”. I’m all about looking classy, but also having fun. And I believe those two things can work wonderfully together. A great date night look, in my opinion, incorporates black and red. If you’re going to a sit-down location, here’s a classy, sexy, and fun look:

lipstick-femme date look

Dress | Missy Empire $23.92
Earrings | Dior
Bag | alice + olivia $295
Shoes | Christian Louboutin $895

This look is great for a restaurant date, or if you’re going to see a production. I for one love dates to see musicals and plays, and I looove dressing up for them. This look is classic in red, shows off your curves, and adds some quirkiness to your outfit with the addition of the fun clutch. I’m a sucker for cute, quirky accessories like alice + olivia’s Stacey Face Mini Bag.

For a more active day date, say you’ll be walking around a lot, below is a cute, “girly” Femme look.

femme date look

Sweater | $52.90
Skirt | CNlinkco (via Amazon) $11.99
Sunglasses | NASTYGAL $40
Necklace | Call It Spring
Bag | NASTYGAL $88
Boots | Rampage (via Nordstrom rack) $69

This look is flirty and fun, but also practical. Wedges are a great idea if you’re like me and love the lift but also want to insure comfort for the duration of the date. There’s nothing worse than being on a date and worrying about pain from heels when you should be enjoying yourself and your company. I love skater skirts, but for girls on the taller side (like me), wearing fun tights is an option that also works great as the weather gets cooler.

My advice that I give to all my friends when asked about date fashion is to choose colors, patterns, etc. that accentuate your personality first, your looks second. And always dress for comfort. If you know you’ll be walking a lot, go for your comfiest pair of wedges, or your favorite flats or sandals. Fashion is one of the best ways of expressing yourself, because first impressions are usually visual. So give your date the best impression by showcasing your personality through your style.

Good luck!

  One thought on “Date Nights & What to Wear

  1. October 15, 2014 at 10:50 am

    Agreed– dressing for dates (especially a first date!) is always a challenge. I’m not sure if it’s better to be over, or under dressed! For first dates I always prefer a super casual setting, I find that if I’m going somewhere too fancy I can’t really be myself.


    Liked by 1 person

    • October 17, 2014 at 1:10 pm

      Agreed! First dates are best when they’re casual. You’re already worrying about making a great impression, it just adds to the pressure when it’s somewhere fancy.


  2. Mel
    October 14, 2014 at 9:38 pm

    Cute outfits! Love that red dress!

    Liked by 1 person

    • October 14, 2014 at 9:56 pm

      Thanks! I know right? I’m obsessed with finding a similar dress now. Or maybe I’ll cave and buy that one! haha


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