It’s almost here, that vacation and break from our winter {well here in Wisconsin anyway}. Am I the only one that feels like I need a new wardrobe for trips? I mean, I had clothes last summer, where did they all go?…anyway, I guess styles change. If you’re headed someplace warm or just want to dream of your summer wardrobe, I have picked some of my favorites that are out right now. I’ve spent many hours clicking around finding some of the best for you, and it’s all right here. Each category showcases a variety of price points, some items I own, some I’ve ordered, and some I am just lusting over.

Dresses
I live in dresses in warmer weather. I am not a big shorts person. I find dresses are easy, comfortable and what I reach for most often. I also love a good jumpsuit or romper so I’ve included some of those as well.
I’ve linked a variety of dresses from casual like this – perfect for beachside lunch to more elegant like this, perfect for a candlelit dinner. Hands down, a classic and flattering dress for so many body types is this dress. Every woman that’s ever tried it has loved it! It’s one you’ll reach for time and time again and it timeless.
**Just a side note – I really dislike strapless bras and realize I look better NOT wearing one. I try to find dresses I can wear a regular bra with. Most of these are regular bra-friendly.
Shop Dresses Under $50
Shop Dresses
Shorts/Skirts
I am not a huge shorts fan simply because they are a hard fit for me. I do need a pair or two for running around with the kids so I have a few pair in my closet. I finally jumped on the bandwagon after reading amazing reviews of these jeans shorts – they have a wider leg and a looser fit which is definitely what I’m going for. I ordered them and patiently waiting for their arrival. I do like this style of shorts to dress up a bit. They are comfortable and easy to wear. A great alternative to shorts is skirts. I have this denim skirt and it’s really soft and stretchy.
Tops and Tee’s
As I’m searching for tops I am realizing there are a WHOLE lotta crop tops out there. Not the perfect style for many middle-aged women. I’ll be settling for a lot of basic tees and my trusty bodysuits. I’ll for sure be packing my favorite band tee and this lightweight, less expensive option. Oh! And this $8 tank is amazing – get one in every color! I think I might order this white top – I love this style with jeans, jean skirts or shorts…but it’s kind of expensive.
Shop Tops
Swimsuits
Everyone’s favorite, right?! Last year was my first year wearing a high waist bikini. I absolutely LOVE these bottoms. They are THE BEST and most flattering ever {also come in plus size}. Get those basic black bottoms and pair any top with them – it can be a bikini or tankini style. I paired them with this really comfortable top last year and it was a favorite suit.
This year I opted for another high waist two-piece. This top has underwire and the bottoms fit like a glove. I love the classy belt detail.
I also love this two-piece where the top is sold by bra sizes {has underwire too!}. The bottoms are flattering and full coverage too. I had this suit in a different color last year and loved it.
A great one-piece option is this suit with underwire too! Such a classic that you’d have for years. I can’t say enough great things about it!
Shop Swimsuits
Cover-Ups
I LOVE a good cover-up and on vacation, it seems to be the most worn item. I really like a simple sarong option. This one for $12 is awesome! I’m in love with this bright-colored one that’s a bit more of an investment – but it’s gorgeous! I also love shopping at Francesca’s for cover-ups. This is a fun one!
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Sandals
Sandals are my weakness! This year we are seeing some bling on sandals {yay!}, a square toe and a kitten heel as all the rage. I am thinking this pair covers all those trends and would go with everything- I think I may order them. I also love this pair for the pool and beach. I’m a sucker for a bow! What about adding these to my cart – they’re only $30! This pair of espadrilles go with everything and was a staple for me last summer. Plus, they are a great price point.

Shop Sandals
Totes and Bags
We are still seeing lots of wicker and natural elements in summer purses and bags. I can’t believe these bamboo bags are still so popular! I love mine – it definitely adds so much style to any vacation look. A rectangle shape tote with the round handle is really trendy – I can’t believe this one is $40!
I love my round wicker tote from last spring – the tassels are such acute detail. This one is really similar and so fun. I am so in love with this little crossbody – I mean…don’t you think I need it?! I just ordered this tote. It’s a knock off of a much more expensive brand {which I don’t do often}, but I can’t get myself to pay $300 for this…the $18 version will do just fine!
Shop Bags
Sunglasses
I don’t buy designer sunglasses any longer! I have lost or broken a few nice pairs since being a mom and it’s gut-wrenching. I’m in love with Quay sunglasses. They have great styles, quality, and, price points. These are all in my repertoire and I love them all so much!
Shop Sunglasses
Sun Hat
I’m just going to leave my new favorite here. This hat is all the rage in the blogger world – I love it and saw it in person. However, it’s quite stiff and wouldn’t at all be packable. I opted for this ALMOST identical hat {same barrel} that is much more flexible and packable. You can also adjust the size with a tie inside, plus….it’s $39!
Shop My Sun Hat
Ok, hopefully all you need now is your sunscreen and to create a killer beach playlist! Add any one of these items to your vacation suitcase and I think you’ll be so happy!
As always, thank you for reading and make it a great day!
Some photos for this post are by Kaley Rae Photography
