A Fashion & Lifestyle blog by Tobi.com, featuring fashion inspiration, beauty tips & tricks, travel guides, delicious recipes, fitness & health routines and more!

Style Guide: Fall Date Night Outfits source: tobi.com
Creepypasta: Our Top 7 Terrifying, Bone-Chilling Creepypasta Tales Guaranteed Keep You Up at Night
Creepypasta: Our Top 7 Terrifying, Bone-Chilling Creepypasta Tales Guaranteed Keep You Up at Night

Style Guide: Fall Date Night Outfits

Getting all dressed up to go out and being in love, or even just a deep enough like, are two things most of us can agree are a pretty good time. Getting dressed up to go out because you’re in love can be even better, especially when you’ve mastered the date night outfit to the extent of being able to look your flirty and fashionable best at a moments notice; remaining open to spontaneity and looking amazing while you’re doing it.

Like all things, perfecting the art of the date night outfit can only be done through experience, and a tip or two from someone who knows. So here are some outfit ideas for date night:

  1. Casual First Date Outfit

    The best thing about a first date is the thrill of potentially finding a long-term S.O. Most often, these dates are super cas’, so you don’t want it to seem like you’re trying too hard. Pair classic basics with chic pieces to elevate an otherwise simple everyday outfit. A sweater dress is the perfect go-to when it comes to merging casual with slightly dressy. Try a romantic hue like a wine colored knit dress, and pair with your fave ankle booties. You can even opt for sneakers to dress it down!

    We’re also really into a comfy flannel and short combo for a casual date–you can never have too many flannels! Plus, they’re super versatile and the ultimate laid back cool-girl piece to have in your collection.

  2. Dinner Date Outfit

    This can mean a lot of things so keeping it simple and chic goes a long way. Flirty basics like slip dresses, which are back in all of their 90’s glory, in a wine or deep olive color, can make for great staple pieces for the fall; looking back a little, something in a blush could be great for when the weather feels a little warmer.

    Add a little attitude to a very feminine dress style with something classically chaotic, like a slightly oversized camo jacket. It’s the sort of outerwear that can go from optional to essential like that. Show you’re date that you’re totally comfortable in your own skin by being bold—mix it up on your night out. We also love statement outerwear like this with classic skinny jeans and a simple blouse.

    Let the accessories set the tone from there; throw on your favorite necklace, earrings, or rings to kick it up a notch.

  3. Happy Hour or Bar Hopping Outfit

    For happy hour or bar hopping, you definitely want to keep that laid back vibe in your outfits. Especially if you’re going to be dancing and drink, you probably want to be comfortable, but still want your personality to shine through. A blouse and trusty black jeans that are appropriate for the office can also be perfect for happy hour or drinks after. With a quick switch of your shoes and accessories, you can be bar-ready!

  4. Gallery hopping or Museum Date Outfit

    If you’re doing this right, it usually means hitting a bar or club once you’ve passed through each show, so fashion and function are important because long hours of lots of moving around is what it all comes down to, and you want to be cute and comfortable. A dress is perfect for this occasion since you can wear it dressed down or styled up! The right dress with heels that you look great and feel good in, creates a romantic look that can be dramatized or sweetened with the help of strategic makeup choices. Emphasize your artsy side with a fashion-forward piece with eye-catching patterns and/or colors!

  5. A date in the great outdoors

    Maybe you’re going somewhere like the Hi Line in New York, a modern park in the middle of a big city, maybe you’ll take a hike or do something totally random like visit a botanical garden, whatever the case, denim is the answer; as it so often is. Pairing a casual pair of boyfriend jeans with a top that comes across high fashion and fun will always be a winning look, and ankle booties or slip on sneakers with a slight platform are all you need to perfect that vibe.

  6. Concert date

    There’s basically a uniform that exists for concerts, and there’s really no need to stray too far from what has been established. Wear your best jeans, maybe a leather skirt, and a simple T-shirt, and update outfits like this with stylish embellished denim outerwear which seems instantly timeless in the height of its trendiness. Embrace and then mix up the double denim look with denim heels or booties in a contrasting wash and you’re good to go!

  7. Formal Date

    Formal dates are inevitable in any relationship. Whether you’re a plus one for a company party, or someone’s wedding date, be ready for what’s to come! In these cases, you’ll want to make a good impression on more than just your date. Dresses veering on the more classy & conservative realm do a great job of doing just that. Find out what silhouette works for your body type, your color of choice, and don your favorite dressy heels & earrings.

  8. Meet the parents

    Meeting the family or friends of your special someone (they’re probably pretty special if you care about meeting their parents or friends) is a big event, and it could be said that the type of outfit you style for something like this could be a blueprint for any commemorative dates going further; like holidays and birthdays. As a matter of fact, that’s exactly what’s being said here and now. A blouse is the way to go when you want to look put together. Pair with your fave pair of denim or black jeans, and you’re ready in a pinch!

Whatever you’ve got planned for date night, let these outfit ideas be the spark. Get your creative juices going, and get in front of a mirror. You’re expressing yourself as much as you’re making an impression, and that’s the best part.