WEEKLY WRAP UP
I began my date night outfit series last July when I shared sixteen looks for the summertime. It was my most viewed blog post of 2020 and, to this day, still gets thousands of views each month. Although I’m certainly no dating expert, when asking what you wanted to see on the blog this month, an overwhelming number of you said a part 2 to this series, so I’m making it happen!
However, this time around I’m stepping up my game and sharing twenty outfit ideas for twenty different occasions. The date ideas came straight from you (via Instagram) and I did my best to cover them all.
Plus keep in mind feeling comfortable and confident in what you’re wearing is key! I’m known for being a little “over the top” when it comes to my outfits, so these outfits may seem a little dressy for some of you—feel free to follow this guide loosely and recreate as you please!
Picnics were without a doubt the most popular answer when asking what dates you were going on. They are essentially free and a good way to get some fresh air so I can see why! While you could totally sport a tee shirt and shorts, why now wear something super cute and grab a photo while you’re at it?! This gingham two-piece set screams picnic in the park and is the cutest mix of white and sage green. Throw on a pair of platform sneakers to keep things casual.
Outfit Details— set: Romwe, sneakers: Steve Madden, earrings: Walmart, necklace: The Silver Heron, rings: Ana Luisa, bracelets: Ana Luisa
My ideal date is a day at the ballpark! Keep things sweet and simple for this date— a high neck tank and a pair of denim shorts are all you really need. These ones have a boyfriend-like fit and just the right amount of distressing. My platform Converse are the perfect shoe for walking around the park! Don’t forget to layer up on gold jewels and grab a pair of sunnies. If you have a jersey, wear it open layered over top for an instant cool-girl effect.
Outfit Details— tank: Forever 21, jersey: Romwe, shorts: Forever 21, socks: Forever 21, shoes: Converse, earrings: SheIn, sunglasses: Discount Glasses, necklaces: Ana Luisa, rings: Ana Luisa, bracelets: Ana Luisa
Oh, how I wish I had a boat to go on! My sister’s boyfriend does and they go on these dates often. Sometimes she’ll wear a swimsuit with a cover-up over top and other times she sticks to a regular outfit if she’s avoiding the water. A crochet tank and high-rise shorts are the perfect combo if you’re going that route. When spending a day by the water, I always reach for my straw accessories. My earrings are old as is my bag but I’m linking similar. This bag is the perfect size for a swimsuit, your phone, and any other essentials.
Outfit Details— top: Fashion Nova, shorts: Express, shoes: SheIn, bag: SheIn, earrings: Walmart, necklace: The Silver Heron, rings: Ana Luisa, bracelets: Ana Luisa
Brunch is hands down my favorite meal of the day. I could eat bacon and eggs all day every day! Most places around me are super cute so this is one occasion I’d throw on a sundress for. I’m a sucker for anything mustard and this sweet swing dress has the most adorable tie-side details. I kept things monochromatic and popped on a pair of mules from Lulus + bold floral statement earrings.
Outfit Details— dress: Romwe, shoes: Lulus, earrings: SheIn, necklace: The Silver Heron, rings: Ana Luisa, bracelets: Ana Luisa
I so wish we had a drive-in theater closer to us. To my knowledge many states have them and it seems to be a hot spot in the summertime. For just a small fee you can enjoy a popular film from the comfort of your car! I’d keep things super casual for this: boyfriend-length sweat shorts and a seamless tank are all you need. It’s comfortable yet cute. Although I tend to kick off my shoes in the car, platform Converse look best with this.
Outfit Details— top: Forever 21, shorts: Forever 21, socks: Forever 21, shoes: Converse, earrings: SheIn, necklace: The Silver Heron, rings: Ana Luisa, bracelets: Ana Luisa
Headed to grab coffee at the local hotspot? Do it in style with a cute peplum tank and your favorite pair of jeans. I know skinny jeans are on their way out but I still can’t get enough of them! These are from Express. Just a simple white sandal and a few gold jewels complete this look in no time.
Outfit Details— top: Romwe, jeans: Express, shoes: Franco Sarto, earrings: Walmart, necklace: The Silver Heron, rings: Ana Luisa, bracelets: Ana Luisa
There’s nothing more embarrassing yet ~stupid fun~ than bowling. Although it’d take the right guy for me to agree to go! Because you end up changing into ugly bowling shoes, I recommend something super simple. Just a graphic tee and high-rise shorts will do. These are from Express! I’m wearing Converse with this but of course, they won’t be on my feet for long.
Outfit Details— top: Romwe, shorts: Express, shoes: Converse, purse: Romwe, earrings: SheIn, necklace: The Silver Heron, rings: Ana Luisa, bracelets: Ana Luisa
Golfing is one of my favorite summer activities—I tag along with Connor and Chase quite often and it’s always a ball! Most golf courses have dress codes but to my knowledge, a tennis skirt is always appropriate. I love pairing mine with this longline sports bra from Spanx. It gives off “cropped tank” vibes but still has tons of support. I’m obviously no pro so white running sneaks are my shoe of choice. This would also be a cute fit if you wanted to hit the local mini-golf place.
Outfit Details— top: Spanx, skirt: Spanx, sneakers: Adidas, earrings: SheIn
For all my 21+ ladies, grabbing drinks after work seems to be one of the most common dates nowadays. This strapless top laces up the sides for a sexy accent. I’m slipping into black jeans—my go-to for a confidence booster and a night out. Matching heels, gold hoops, and a chain bag are all I need to feel like a total bad a$$.
Outfit Details— top: Romwe, jeans: Express, shoes: SheIn, purse: SheIn, earrings: SheIn, necklace: The Silver Heron, rings: Ana Luisa, bracelets: Ana Luisa
Being just an hour from Baltimore, the aquarium is definitely a summer hot spot. There are lots of places to eat + window shop around the area so a cute top and denim shorts are very fitting. I went with white shorts to keep this look bright and a pair of gold lace-up sandals to elongate the legs. You’ll want a flat shoe as there’s a lot of walking involved on this date.
Outfit Details— top: Romwe, shorts: Express, shoes: Express, earrings: SheIn, necklace: The Silver Heron, rings: Ana Luisa, bracelets: Ana Luisa
Connors fam and I still get together to this day for cookouts. I almost always will wear a romper over. They’re appropriate around the family, cute for photos, and perfect for playing corn hole. I love the bright color palette of this SheIn one! You know I’m a sucker for white shoes so I’m slipping into my current fav espadrilles from Franco Sarto. Grabbing a straw bag to match + carry my phone, wallet, and vlog camera.
Outfit Details— romper: SheIn, shoes: Franco Sarto, earrings: Walmart, purse: SheIn, necklace: The Silver Heron, rings: Ana Luisa, bracelets: Ana Luisa
The winery was a popular answer for those of you in long-term relationships. To my knowledge these tend to be a bit dressier than your average place so why not throw on a cute wrap dress?! I feel like these are the perfect in-between style. Super easy to dress up or down. I’ve got on nude heels and my favorite butterfly earrings to tie the look together.
Outfit Details— dress: Romwe, shoes: Target, earrings: SheIn, purse: SheIn, necklace: The Silver Heron, rings: Ana Luisa, bracelets: Ana Luisa
If I’m being honest, the zoo as a first date sounds like my worst nightmare. But, I know so many people who love going. It’s always so hot being out in the sun so I’d go for a tank top and shorts. With lots of walking, my Converse are a must. I’d also recommend reaching for a crossbody bag. This three-piece style fits all of the essentials + keeps the weight off your shoulders. I have this bag in a gazillion colors and it’s the best!
Outfit Details— tank: Forever 21, shorts: Forever 21, socks: Forever 21, shoes: Converse, sunglasses: SheIn, earrings: SheIn, purse: SheIn, necklace: The Silver Heron, rings: Ana Luisa, bracelets: Ana Luisa
Fingers crossed more concert venues begin to open up now that Covid has mellowed out a bit. I’m dying to see Jon Pardi or Cody Johnson in theaters this summer. A scarf top paired with denim shorts is the perfect combination for a fun night of singing and dancing. If it’s a country concert, it’s the perfect excuse to break out those cowboy boots and hat!
Outfit Details— hat: Justins Boots, top: SheIn, shorts: Fashion Nova, shoes: Dingo, necklace: The Silver Heron, rings: Ana Luisa, bracelets: Ana Luisa, earrings: SheIn
I’m not the most outdoorsy gal you’ll ever meet—while I’m not a huge fan of taking the off-the-beaten-path, I’m happy to walk and talk along a local trail. As long as someone can keep me entertained I can go for miles, lol. These seamless tanks are the best thing in the world. They come in a four-pack from Romwe, are just the right length+ have pads! They pair awesome with my Lululemon shorts and new Adidas sneaks.
Outfit Details— top: Romwe, shorts: Lulu Lemon, shoes: Adidas
Museums are a fun idea for a hot day—perfect when you need to get out of the sun but still want to see some sights! I recommend something a little more conservative. A puff sleeve dress is perfect. Again, this is one date where I’d recommend a flat shoe. Either sneakers or cute slides would work just fine. I know some of these places don’t allow big bags; to play it safe you can’t go wrong with a clear purse.
Outfit Details— dress: Romwe, shoes: SheIn, purse: SheIn, earrings: SheIn, necklace: The Silver Heron, rings: Ana Luisa, bracelets: Ana Luisa
There’s nothing better than getting dressed up for a good meal. I love trying new places and rating them with friends and fam. This black tie-side dress from Romwe is super sexy. With black block heels, it elongates the legs big time. It’s also works well as a wedding guest dress too. If anyone wants to take me to dinner— you know where to find me 😉 (kidding, but not)
Outfit Details— dress: Romwe, shoes: SheIn, purse: SheIn, earrings: Walmart, necklace: The Silver Heron, rings: Ana Luisa, bracelets: Ana Luisa
Amusement parks are finally opening up! I know some people like to “dress up” for a day at the parks but I personally prefer something a bit sportier. A seamless tank and tennis skirt make the ultimate combo. I always wear close-toed shoes and a crossbody bag that’s big enough to fit the essentials but small enough to fit in the little cubbies. Bonus points for this skirt because it has pockets!
Outfit Details— top: Forever 21, skirt: TJ Maxx, sneakers: Adidas, purse: SheIn, earrings: SheIn, sunglasses: Discount Glasses, necklace: The Silver Heron, rings: Ana Luisa, bracelets: Ana Luisa
Bonfires are a pretty typical event around here. They’re a super laid-back way to get together with friends. Plus, I’d never turn down a smore. Jeans and a white tee are all you need for this occasion. I like to keep things casual + wear clothes that are easily washable to get the smokey smell out of. For shoes, I’m slipping into a pair of white Birks.
Outfit Details— top: Whitefox Boutique, jeans: Express, shoes: SheIn, earrings: SheIn, neckalces: Lulus, bracelets: Ana Luisa, rings: Ana Luisa
I’m dying to go to the fair. Even if you don’t ride the rides, it’s so fun to play the games, eat a funnel cake, and just walk around. A bandana top seems like the perfect piece to wear. Although if you’re planning on going on any rides, I’d probably stick to something with straps. Denim shorts are a must as are close-toed shoes. Reaching for my Converse yet again.
Outfit Details— top: Romwe, shorts: Express, shoes: Converse, earrings: SheIn, necklace: The Silver Heron, rings: Ana Luisa, bracelets: Ana Luisa
pin this post to refer back to before your big outing!
Because this post was so highly requested I will definitely do another one when the seasons change! I cannot lie, I had a lot of fun putting together this post. Now if only someone would take me on one of these dates, lol!
I hope you found this post helpful and that it gave you some outfit inspiration + date ideas for the upcoming months. Let me know what else you need help styling this season!
With love, McKenz