First dates can be one of the most difficult occasions to dress for. Not only do you have to consider the weather, the location, and the walking distance, you also have to try and strike a balance between your own personal style and something first-date appropriate. It’s no wonder most of us enlist a friend or five for second opinions and have several pre-date meltdowns along the way. However, worry not, as these ten first date fall outfits are sure to appeal!
This is a classic. The cinema date has been around for decades and is a good option if you’re unsure about how interesting your date actually is. You could always extend the date if it’s going well! Cinemas are either boiling hot or uncomfortably cold and so the key is layers. I would say to go for jeans paired with a cute slogan -shirt or a vest top you can put a denim or leather jacket over, and pair the look with some shoes you can wriggle off if you have empty seats on either side of you – classic, but simple, and you won’t be awkwardly shivering or sweating so much you can’t concentrate on the film. This is one of the best first date fall outfits!
Another popular option, especially now, in the age of internet dating. You can escape after one drink if it’s really not going well or set up a tab if it’s going far better than you expected! There are a variety of bars out there with different dress codes, but I would say a fail-safe option is either jeans, a strappy top paired with statement jewellery, and a block heel, or a cute, floaty dress with some flat or low-heel shoes. Bars tend to be quite warm, but if you like you can sling a coat on with either of these options, as long as it isn’t so padded it looks as though you’re heading to the North Pole!
Much like the drinks date, a coffee is perfect if you feel nervous about meeting somebody in the evening, or you don’t feel confident enough to commit to something more serious. The Autumn breeze can often be vicious, and you don’t want to stick out too much in a daytime environment, so I would stick to what you would wear every day for this one, maybe with some low-heeled boots and some slightly nicer jewellery – the trick is to look as though you made an effort but didn’t dress up specifically for the date!
Whether you know the artist/s well, or this is the first time you’re seeing them, concerts are a good way to gauge what some of your date’s interests are. Plus, if it’s awkward, you can focus on the music instead of how badly the actual date is going! For this I would say, depending on the type of concert it is, both heels or flats are acceptable – but if you’re going to wear heels, make sure they’re comfortable because you never know if you’ll be standing! Other than that, a glitzy crop top paired with mom or skinny jeans is always a good idea.
Going to a museum or art gallery for a date seems like a less likely choice, but for those who bonded over art or history, or both work in the creative industry, it can be a nice change from the bustle of bars or the expense of the cinema. This date idea also gives you more freedom to express yourself as you’ll be among artistic types! Think slightly oversized jumpers tucked into skirts or mom jeans paired with slingback loafers or mules – you can even add some glasses if you’re feeling particularly artsy in these first date fall outfits.
You don’t want to arrive in jeans and a t-shirt, but most of your dresses seem too fancy. Also, you don’t want to run into anybody you know whilst on the date and feel awkwardly overdressed. The solution – ankle boots with no more than a four-inch heel, a pair of dark skinny jeans, and an off-the-shoulder top. This makes for one of the best first date fall outfits. Simple enough to be dressed up, but it won’t look out of place in a place filled with both children, old people, and those of your own age.
This doesn’t necessarily have to mean you’re going to a Michelin-starred restaurant, but perhaps your date has money they want to burn by taking you to a place nicer than your local Indian restaurant. This one can be tricky, because you don’t want to underdress or overdress. Heels are a must for this one, and I would say to stay away from jeans unless the dress code allows them. Go for a dress in a silhouette that flatters you and do your makeup in a classic and understated way – think a subtle smoky eye and red lipstick. This is one of out favorite first date fall outfits!
Channel your inter vintage girl for this one – it’s time for a picnic in the park. Depending on the weather, and the general muddiness of the ground, a picnic can be a really cute and relatively cheap first date that has a more laid-back vibe than the others. I would say to go for a co-ord top and trouser situation, or for a checked dress like the ones seen all over the catwalk and high street. Unless you’re very confident walking on grass in heels, I would opt for flats in this situation, and definitely bring a jacket to sit on so you don’t end up with a grassy bum!
As people search for first-date ideas out of the box, options like mini golf and bowling, previously thought of as for children, become more popular. Dates like this are all about having fun with some healthy competition, and there’s plenty of room for flirty banter – dress down in jeans, a slightly oversized tee, and some statement trainers, with hair and makeup fresh and minimal. You want to look as though that rosy glow is all natural! This is one of the perfect first date fall outfits!
Okay, so you’ve confirmed the date, picked a time, and are (mostly) looking forward to it. But where are you actually going? It could be to an aquarium, a zoo, for a hike, or even something off-the-wall and unexpected like paint-balling – your date insists on keeping it a surprise. First step is to not panic! Go for versatile bottoms such as jeans or culottes that work for several occasions. Definitely stick with flats – you don’t know how much activity you’ll be doing! Pair these with a cute crop or cami and stick a jacket over the top – bingo! Wear a jumper if it’s particularly cold and pack a bobble and a necklace in your bag in the event of needing to dress up or down. Sorted!
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