Wear Your Mood: First Date Outfit Ideas

August 21, 2014
first date outfit, how to style, romper, tobi, style by alina, fashion blog

First dates can be so fun and exciting so the last thing you want to do is stress over what to wear on the day of. I’ve made my fair share of mistakes in the past by procrastinating until the very last minute deciding what to wear. The feeling of being rushed has led me to make some regretful fashion choices and made me feel subconscious and distracted throughout the date. You definitely don’t want that to happen to you! To feel confident on your date you have to feel comfortable with what you’re wearing. At least one day before the date, pick out two outfits that best reflect on your mood and is appropriate for the location of the date. Obviously, if you’re going for hike or a casual outdoor activity, you definitely want to leave those 4 inch high heels at home. =)

So how do you decide what to wear for your first dates? Here are some first date outfit ideas that won’t leave you second guessing yourself.

Comfy Chic
When in doubt, this is always to go-style. You can never go wrong with a pair of skinny jeans and cute blouse. Add in a pair boots or pump and you’ve just taken the comfy chic look up a notch. While we fuss over what to wear, most men actually prefer their dates to dress casually but put together. Why? Chances are they are just as nervous as you are. So the less dressy you are the more approachable you appear and the more comfortable your date will feel around you. It’s much easier to break the ice when you both don’t feel like you have to impress each other and what you’re wearing can make a big impact.

Classy Feminine
Sometimes you just want to feel like a girly girl on your first date and there are plenty of options for this look. Rompers, skater dress and skirts, maxi dresses and jumpsuits are some great choices.  In this feature I’m wearing a mixed pattern romper from Tobi. Pairing the romper with black pumps and a light jacket adds a dash of elegance to the look.

If your first date is during lunch time and on the weekday, you and your date will probably be in your work clothes. For this type of date, I usually go for something sophisticated but feminine. A tailored work dress or pencil skirt and blouse are my to-go choices.

first date outfit, how to style, romper, tobi, style by alina, fashion blog

first date outfit, how to style, romper, tobi, style by alina, fashion blog

first date outfit, how to style, romper, tobi, style by alina, fashion blog

Romper – c/o Tobi
Shoes – BCGeneration (old, similar HERE)
Jacket – H&M (old, similar HERE)
Bag – Amazon (old, similar HERE)

What is your to-go first date outfit?

  • Courtney Bella

    i love the jean jacket !:) and the blue dress! thank you for sharing! xoxo

  • Rosie

    those are all nice looks for a first date!!! Just hearing the words ‘first date’ gives me jitters, so if I need to get ready, I better find something like this and be prepared to have a great time and look great, too!

  • Courtney Bella

    love the jacket! been looking fora good denim jacket for a while now

  • Shannon Sampsel

    love all of these looks! the romper is to die!

  • Viviana M

    That light blue jacket is serious!

  • Rachael Schauer

    I’m OBSESSED with that Romper!

  • Diana Scholz

    This is seriously the cutest romper EVER!

  • Brandi B.

    Love all of these looks, especially the pink pants and white blouse one!

  • Courtney Bella

    you are so pretty and i love the denim jacket. i want it !:) xoxo

  • Armel Madsen

    love the onesie shorts :)


  • maggie

    I love the first outfit you put together. It kind of says, “I’m laid-back and casual, yet fun.” Totally loving your clutch too. You look gorgeous Alina. :)


    Maggie S.


  • Dana Prigge

    Gorgeous! Love the look!
    Dana of Bella NYC Magazine
    Owner: DailyFashionista.com

    • http://StyleByAlina.com/ StyleByAlina.com

      Thank you Dana!

  • tracey

    I like your romper! I think it will go well with black blazer as well! ;)


    • http://StyleByAlina.com/ StyleByAlina.com

      Thank you Tracey!

  • Emma

    Love how it looks like a dress!

    Emma| With A City Dream

    • http://StyleByAlina.com/ StyleByAlina.com

      Thank you Emma!

  • Jess galfo

    This looks amazing on you!! Love how you styled it.

    xx Jess

    • http://StyleByAlina.com/ StyleByAlina.com

      Thank you Jess!

  • http://alinaermilova.blogspot.com/ Alina Ermilova

    Love your outfit variations! I think dress is a classic, you simply can never go wrong with it! ;)



    • http://StyleByAlina.com/ StyleByAlina.com

      Thank you Alina!

  • Eni K.

    Hi Alina and thank you very much for your visits to my blog. Sorry for not having answered before, but I was on holiday. You are a very expert of looks. I like very much this outfits, especially Classy Feminine and Sophisticated. This black shoes of BCGeneration are amazing!!! Kisses,


    • http://StyleByAlina.com/ StyleByAlina.com

      Thank you Eni!

  • http://stylesensemoments.blogspot.com/ Marija

    Love the suggestions, I’m always for comfy chic! ;) That romper is gorgeous, love the pattern, so different! xo

    • http://StyleByAlina.com/ StyleByAlina.com

      Thank you Marija!

  • Jackie Harrison

    Looking stunning and elegant


    • http://StyleByAlina.com/ StyleByAlina.com

      Thank you Jackie!