The Ultimate Guide To Date Fashion

Hey Fashios!

How many of you have been getting ready for a date only to come to the tearful conclusion that you have absolutely nothing appropriate to wear and you’ll just have to cancel? Whether it’s a nerve wracking first date, an important anniversary, or just a usual getting dinner and watching a movie, you still want to look and feel your best. This is where my Ultimate Guide to Date Fashion will help you. I’ve broken down this guide into my favorite date ideas, with an outfit for each. They cover all the seasons, so it will be a great resource no matter the day. I hope that this will offer you some peace and give you confidence to have a great time with your special someone!

Picnic

Spring is the best time to go on a picnic date! The weather is just warming up, but it isn’t as hot or buggy as the summertime, so you won’t have to worry about packing a whole bottle of bug spray if you choose to go somewhere with a more scenic setting. As for what to wear for your date, layers will be your best friend. The temperatures of spring can vary pretty quickly, so wearing a light jacket will help you be ready if the temperature drops or suddenly rises. I would wear comfy but cute clothes that you wouldn’t mind if they got a little bit of dirt on because face it, you will be sitting on the ground outside. Dirt is inevitable. Depending on how warm it is, you could wear a sundress, but I would suggest wearing a dark wash of skinny jeans or leggings with a light colored cotton shirt and a jean jacket or cardigan. You can accessorize by adding in some long delicate necklaces and a cute pair of ankle boots or sneakers! Pink is universally flattering for makeup and will compliment your features and add a nice healthy glow to your face, even if you’re a bit pale from the long winter. Pick your favorite blush and tap it on the apples of your cheeks and sweep across your eyelids. Finish the look with some mascara and lipgloss and you’ll be looking like a natural beauty!

Movies

The movies are one of the most classic date ideas. Spring can have unpredictable weather and my favorite thing to do during a rainstorm is watch a good film and eat some popcorn slathered in butter. Even if you're sitting in the dark and can’t see each other for two hours, you still want to look good for you hunny. Now, the movies brings up a debate. Comfort vs. Fashion. Personally, I like to find a way to achieve that cute but super comfy look for the movies. If I’m wearing jeans that dig into my stomach or just a t shirt that leaves me cold, I’ll be too focused on how uncomfortable I am to even enjoy the movie, let alone feel cute. This is the perfect opportunity for busting out your highly fashionable but also comfy athleisure outfits. You know what I’m talking about. It’s time to steal that hoodie. So, if you have secured the greatly sought after “boyfriend hoodie” or just have an oversized crew neck or hoodie, your main part of your outfit it set. By wearing a hoodie, you can sit however you’d like, without having to worry about how your boobs or stomach look in the moment because the loose look disguises any rolls. If you don’t have a hoodie or you’re afraid it won’t keep you warm enough, I suggest investing in a Huggle. This is a giant hoodie made of a fleece blanket and it's amazing. I’ve written a post about it before, so feel free to check that out! You could wear some comfy athletic shorts or leggings with a pair of sneakers and boom, you’re set for comfort and cuteness!. As for hair, I’d suggest a messy bun, or two french braids. This will keep your hair from getting messed up by the movie chair headrest, and will still give you a feminine look. Honestly, I don’t wear makeup to the movies very often because 1. I cry easily 2. I fall asleep easily and 3. I rub my eyes a lot. I’d suggest just going with an easy mascara and lip balm look with maybe some brow gel if you’re feeling it. If you want to add an extra spice, tap a cream highlighter along your cheekbones, your cupid’s bow, and in the corner of your eyes. I suggest using a beauty blender to really make sure your highlighter is blended well along your cheekbones to give your a natural glowy look.

Bowling

I love bowling! It’s a fantastic way to break through any first date jitters through some causal competition. I have always loved going on Saturday nights and dancing around to the classics playing and goofing off. Maybe it’s just because most bowling alleys seem to be stuck in the 70s and 80s, but I love going for more vintage and relaxed looks. You want an outfit that will make you look like a dream from the past, but also will give you enough movement to have great bowling form and kick ass. I’d suggest going for more of a vintage feeling statement shirt. A simple button down, or a brightly colored t-shirt secured from your local Goodwill paired with some high waisted mom jeans will give you a stronger 80s/90s feel to your look! You won't have to worry about wearing any special shoes because of the bowling shoes, but some spunky socks can add a little extra oomph to your outfit. If you want, feel free to add a cuff to the bottom of your jeans to flirt and show a little ankle. If you feel like a t shirt and jeans is too plain, I suggest playing with your accessories. Adding in a nice belt with some hoops or dangling earrings that match the buckle can make an outfit much more put together and especially help for making high waisted jeans fit well. Additionally, you could add in a bold lipstick or eyeliner to really make your look pop. You can style your hair however you’d like for this look, but I suggest having it down or at least half down. Loose waves styled with a straightener will give you that “messy cool surfer girl” hair without having to jump into some cold water.

Pumpkin Patch & Corn Maze

It might be a bit cliche, but girls, we all know deep down we’d love to go on a pumpkin picking and corn maze date. Being from Wisconsin, going to farms for pumpkins and some great apple cider is a fall tradition. Similar to Spring, layers are your friend. You want to make sure you can look cute while also staying warm enough to have fun. I’m not sure about you, but when I think of fall outfits, I immediately think of flannel. Yes, it might be considered “basic” but I say don’t fix it if it ain't broke. Flannels come in such an array of colors and cuts that they’re universally flattering for all body shapes and sizes. The pattern also helps to disguise any stains you might get while posing with a pumpkin that’s a bit more dirty that you expected. For a classic fall date, I would wear a white, long sleeved v-neck underneath a flannel. I look green, blue, or red flannels, but any flannel will work. If the weather is a bit colder, you can toss on a light vest or a teddy coat to play around with textures. I would wear a nice pair of distress jeans that match the style of the flannel, but also fit you well enough that you can squat and walk around while searching for the perfect pumpkin. I am a huge fan of Doc Marten boots, so pair your outfit with a good pair of wool socks and boots and then you’re set! You can add in a beanie or scarf for accessories and go for a darker, warm makeup look, maybe with a chocolatey smoky eye.

Going to the Fair

The fair is definitely my #1 favorite date idea for the summer. If I don’t go to the fair and get a creampuff or funnel cake, I didn’t have a successful summer.The possibilities for outfits to wear are endless, but I have a classic one that can be tweaked to fit your own personal style. Because temperature vary, you may prefer a tank top over a t shirt, but I love t shirts so thats what I’m going to go for. I’d recommend wearing a pair of high waisted jean shorts that are comfortable and will cover up any food baby you get from all the fair food. As for the top, I’d wear a loose crop top or cotton t shirt that is cute, but will also keep you cool. Stores like American Eagle and Shein have a great range of colors and styles of tanks and tops that are perfect for the fair. If you want to accentuate your tan, wear light pastels or white. It’ll create more contrast against your darker skin and look fantastic. Remember ladies, never show all of your assets. If you’ve got the booty popping, then cover up a little more on top. It’ll keep you looking classy and keep your dad from trying to kill your date when you come back. I’d wear a dainty necklace or small hoops for accessories as well as some comfy sneakers, like vans. For hair, I’d put it in a ponytail or braid because I love to go on rides and hate when it gets all tangled and matted.

Ice Skating

Similar to a pumpkin patch date, ice skating is a classic date for the winter. It’s great if you’re sick of just sitting inside trying to stay warm, but also don’t want to get too cold. It gives you the opportunity to show off your mad skills or an excuse to hold onto your date as you try not to break your butt. This is another date where you want your outfit to be cute, but also functional. I’d wear a solid pair of leggings that don’t fall down easily, with a cute turtleneck and a knit sweater on top. This should be enough to keep your warm in an indoor skating rink. Make sure to wear thick socks to prevent any blisters. I’d also recommend wearing a solid pair of gloves. It might not be the cutest thing, but if you’re falling down and catching yourself with your hands a lot, the ice will make them painfully cold and raw. Gloves will keep you nice and warm and protect your hands.

Dinner Date

Ah, the classic dinner date. Whether you’re going to Noodles for a cheap and yummy meal or somewhere a bit more posh because his mom said to take you somewhere nicer than Noodles for once, picking the perfect dinner outfit can be stressful. For a more casual dinner, I’d recommend a simple, but cute blouse, a nice pair of jeans, and maybe some boots with a little heel or fashion sneakers. Even if you’re going out to a super casual place, putting in a bit of effort will give you confidence. If you’re going out for a fancier date, I’d recommend going with a classic LBD (little black dress). A simple black slip dress is incredibly femine and flattering, but also shows a bit more class than the casual t shirt and jeans. Before you go rushing off to an expensive store, I’d suggest looking at goodwill. I found an incredible black dress that fit perfectly and it was only $8. If your dress has spaghetti straps, I would suggest wearing a jacket or cardigan to cover up in case the restaurant is cold. You could wear a nice pair of flats or some heels if you can walk in them. I’d go for some soft, romantic curls or an updo for hair. Your makeup can be as glam or as natural as you’d like. Remember to take in the lighting and formality of the restaurant when considering your makeup and dress length. I’d also recommend bringing a purse to keep track of your wallet, phone, and other essentials.

Now that I’ve covered a few of my favorite date ideas and looks, I hope I was a helpful resource. I plan on posting a video in the future of my different easy hair and makeup looks that I would use for dates and that can act as a supplement to give you more ideas!