Summer Vacation Style: Weekend in Chicago

I used to blog about fashion somewhat frequently. Remember that?

I still love clothes and shoes, but have been in a bit of a rut lately. Working from home, combined with the fact that most of my "fun money" lately has been going to house stuff, has meant that I haven't been paying that much attention to fashion. Nobody sees what I'm wearing, so no need to buy anything new.

But that's changed, at least for the moment! I've got an upcoming girls weekend trip to Chicago, so I took the opportunity to buy some cute new summer dresses, and put together my weekend outfit plans. And since I've kind of been OD'ing on the fire pit/house posts lately, I thought it might be fun to change gears and share my summery outfits with you all. Everything in this post is either clothes and accessories I already own, or close substitutes I found online if I couldn't find the originals to link to.

Thursday Daytime: Travel Outfit

I like to be comfortable and casual when I travel. In the winter that means lots of layers, since I'm usually freezing on planes, and in the summer it means shorts, because I am usually hot on planes. I also like to bring a good sized tote bag with me as my carry on, so I can stuff things like my laptop, book, etc inside it, and also have room for a smaller clutch that I will use while traveling as my purse/wallet combo.

Coral shorts, comfy platform flip flops, big earrings, The Sak tote bag (received it for Christmas), blousy satin top (I have the same one in purple)

Thursday Night: Out On The Town

Once I get to the hotel, it will be time for a quick change before going out for dinner and drinks. I love that kelly green is back in style, and so I couldn't resist snapping up this dress from Spool No. 72 (a new-to-me online store that I'm now in love with). One of the best parts is that with the accordion pleats it doesn't really need to be ironed, making it a good straight-out-of-my-suitcase choice. Black accessories, (new) gold jewelry and bright coral nail polish bring together this quick change outfit without a lot of effort.

Black peep toe pumps, skinny black patent leather belt, honeycomb necklace, coral nail polish, kelly green dress, honeycomb earrings, black wristlet purse

Friday Daytime: Lots Of Walking

I've never been to Chicago before, so I know I'll be walking around all day, seeing the sights. Therefore, being comfortable is key, but so is looking cute for all of the pictures I'll be in. Which lead me to purchase another adorable Spool No. 72 dress (although mine has a black top, not blue like pictured below). Pairing that with some comfy wedges and bright accessories will be perfect for being out and about all day long. I'll probably add a red headband too--it is called the "windy city" after all!

Comfy walking wedges, chevron dress, chunky red bracelet, silver earrings, thick black belt (ties in better with the black top of the dress than the yellow belt that came with the dress)

Friday Night:  Boating and Dinner

That night we'll be doing what seems to be a Chicago tourist must do, going on an architectural cruise. So naturally I needed to get another new dress with some nautical white and blue colors, paired with a light cardigan in case it's cool out on the water. And wedges are always a better bet on a boat than regular heels, although I think I'll carry some white flip flops in my purse just in case.

 Turquoise flowered bracelet, color block dress, white cardigan, white wedges with ankle strap, silver earrings

Saturday Daytime:  More Walking

With another full day of walking around sightseeing, another comfy but cute outfit will be in order! I already own a black and white dress from H&M that has a similar flared shape to the one pictured below (although mine is a halter top), so I'll pair that with yellow accessories and yellow ruffled wedges (mine are not as high as the ones pictured though) to complete the look. With this outfit, to dress it up for the evening all I would need to do is to slip on some black patent pumps, and I'd be ready to go if I didn't have time for a full outfit change!

Wide yellow belt, vintage flared back and white dress, yellow ruffled wedges, bee earrings, black wristlet purse

Saturday Evening: Out and About

Hopefully though I will have time for yet another outfit change before we hit the bars after dinner. So I'm bringing a lace and sequin skirt from H&M I've had for a while but never worn, a black satin top, and a coral sweater, just in case it is a cool evening. I think I'll also bring my folding flats in my purse, since my feet might be a bit tired after so much walking over the weekend!

Lace with sequins skirt (this is the closest I could find to my skirt pictured above, which is a personal photo), black satin top, crystal drop earrings, black peep toe pumps, coral cardigan if it's chilly out

Sunday Daytime: Brunch and Travel Outfit

A similar outfit to Thursday's travel outfit, with shorts, a comfy top, comfy shoes and a tote bag. We will also be getting t-shirts to commemorate the weekend, which I'll wear instead of the grey shirt pictured below. Dang it, I haven't even gone on the trip yet, but I already don't want it to end!

Teal shorts, bead and chain necklace, tote, coordinating earrings, t-shirt, comfy wedges

Do you like to buy a few new clothing items for your vacations? Anyone love outfit planning as much as I do? I didn't even show you my, like, 5 backup outfits. ;)