What I Wore in Chi-Town!

Hello everyone, thank you for coming back again this week and welcome to my blog if you’re new!💙 From August 1-7th, I went on my first ever vacation and I chose Chicago as the destination. My birthday was also on the 5th (woohoo 21🎊) so it was perfect timing.

This post is dedicated to the outfits I wore while in Chicago including the thought process, what I was looking for when it came to the look, and links to the items in each outfit or alternatives if I can find one. You may have already seen them if you follow me on Instagram.

Day 1:

I love the Tommy Hilfiger brand especially for streetwear. I spotted this beautiful, simple dress in a Tommy Hilfiger outlet and had to get it. I went with my sisters and after showing them the dress they both immediately nodded saying that it was definitely my style. I also wanted to wear my new New Balance sneakers that were collecting dust in my closet.


Dress: Not online

Sneakers (similar)

Bag (similar)

Day 2:

First outfit was a bikini. I am proud that I could wear it because although people tend to like my body, I am actually quite insecure about it and to top it off, I was bloated because of God’s special gift to all women on a monthly basis.


Bikini Top (similar)

Bikini Bottom (similar)

Second outfit and probably my favorite outfit of the whole trip, was actually quite simple and came as a surprise. I had stopped wearing revealing things because in the past, my intentions were provocative in nature and when I started getting close to God, He would convict me. I didn’t wear this outfit because I was trying to get the attention of any man, but wore it because it was comfortable, chic, simple, and I thought I looked great in it.


Bralette (similar)

Culottes (similar)


Jacket: not online, but a regular leather (faux or real) would do!

Day 3:

I had planned to go shopping so I wanted something comfortable and easy allowing me to change in and out of it quickly. I literally didn’t have this outfit until 2 days before the trip because I had stopped at Target to look at some luggage and saw the jumpsuit and mules instead!



Mules (similar)

Day 4:

My friend and I planned a day full of tourist things so I wanted to look elegant and yet relaxed. I decided to wear the jumpsuit from Forever 21 that I had modified. I took it from strapless to with straps. I wore the shoes I purchased the day before from Express!

After my modification




I wore the dress I brought for church the whole day even though that wasn’t my initial plan. I had to also tweak this dress a little in the chest area to make it church appropriate. I prefer it more open in the chest though so I plan on taking out the stitch I made and instead sewing a hook on allowing me to wear it both ways depending on the occasion.


Birthday dress

Black Steve Madden Heels: purchased at outlet so the price of mine is different than what it says online (almost half off)

Day 6:

This was the last day and I was exhausted. I was ready to go home at this point because we had been doing so much already. I also had horrible blisters from walking so much. I decided to keep it very simple with and off-the-shoulder dress and some super comfortable sandals from Aldo!


Dress (similar): I got mine in stores for $34.99, but could only find this one for $9.99 online so I don’t know how quality compares

Sandals (similar)

Straw crossbody bag (similar)

Enjoy the rest of your week! If you purchase anything, let me know! Like, comment, share to let me know you are enjoying the content!

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: