3 First Date Outfits Perfect for Fall

Getting yourself mentally prepared for a first date can be stressful. You’re meeting a new guy, you probably want him to like you, and you’re just not sure about what to expect overall. This article is not going to help you stop feeling nervous (but this one will). What I can do for you, however, is take away the extra stress that choosing an outfit brings to the equation.

Ah – you forgot about that part, right? You were probably so focused on all the things that could go wrong, or that you hope happen, that it’s now an hour before your date and you have nothing to wear. Or so you think, at least!

Deciding what to wear on a first date has less to do about what he’ll think looks good and more to do with what will make you feel good. Anything you wear should bring you an immediate sense of confidence. The outfit should make you feel proud of your body, and should reassure you that you’re a total catch and the guy you’re about to meet will want to know more about you.

Still stuck? No worries. I’ve broken down three fool-proof first date outfits for fall just for you. First up, we’ll start with something you might wear on an outdoor date – like apple picking.

Apple Picking Perfect

There’s nothing more ridiculous-looking than a woman wearing too little clothing in any setting, but it looks even more ridiculous when it’s cold outside. Cozy knits can be fun and playful, so leave the mini skirt and heels at home when heading out to the orchard. No matter how well you can walk in heels, walking in heels on grass is an entirely other beast that you just shouldn’t tackle when on a first date – trust me.

Grab your most flattering pair of dark denim jeans. Pair them with a silky tank, lightweight scarf, and sexy leather (or faux leather) jacket. Finish the look with ankle boots with a chunky heel. You’ll still get a little lift, they’ll do great things for your legs, but will be able to walk around without looking as if you’re able to fall over.

Date Night Outfit 1

Dinner Date Ready

Have a dinner date planned? Fantastic. You can go a little bit lighter on the layers because you’re probably eating indoors (at least, let’s hope he had the common sense to book an indoor table for a fall date!) and likely won’t be doing too much walking around.

For a dinner date, I love a structured yet fitted dress. Whether you choose to wear tights or skip the hosiery is your call, but I prefer to keep in some extra warmth by slipping on a pair of black patterned tights. They’re interesting, add some style to your outfit, but don’t add bulk. Slip into a pair of high heels and you’re all set. That was easy, right?

Dinner Date Ready

Two Step Style

But, what if you’re heading out for a night of dancing? It’s cold outside but it’s going to get hot out on the dance floor. What’s a girl to do?! Well, that is why they invented coat check. Bring along a $5 bill (just in case he forgets) so you can check your coat at the door. Oh, and I don’t mean your winter parka. Wear a ladylike, fitted fall coat – like a pea coat or cape coat.

Two Step Style

Since you’ll be dancing the night away and want to look stunning yet comfortable, I’d recommend a shoe with an ankle strap. You’d be surprised how much more support they give your ankles, and how much less pressure they place on the ball of your foot. Pair with a flirty skirt and silk tank and away you go! Just don’t forget to grab your coat from coat check at the end of the night, or else you might get a little chilly on the way home.

Which date night outfit could you picture yourself wearing?

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