All The Wedding Dress Shopping Details (where we went, things I wish I knew, our schedule, etc)

I am ~finally~ in full-on wedding planning phase!! Hallelujah. Let’s just say I am not the assertive bride I thought I would be.

A few weeks ago my family flew in and we had the best time wedding dress shopping. I learned so much during the process and thought I would give out all the details from where we went, the top recommended dress stores in Chicago and Milwaukee, things I wish I knew, etc.

Also…can we take a moment for that dress in the first pic?! The only reason I didnt buy this dress was because it was going viral on Tiktok, so I knew a lot of girls would have the same one; but, I was in LOVE. It was so flattering!!

The Top Recommended Dress Stores in Chicago and Milwaukee:

One of my absolute favorite things about having an Instagram is being able to pick your brains on recommendations haha. I asked about the best wedding dress stores in Chicago and Milwaukee and the answers were SO helpful!

When it comes to finding the perfect wedding dress, crowdsourcing recommendations on Instagram can be a game-changer. I’m glad you had such a positive experience with that. The wedding community is often so helpful, and it’s wonderful that you received valuable suggestions for bridal stores.

Among the top recommended dress stores, VA Bridal stood out as a popular choice. Many brides-to-be raved about their excellent selection, attentive staff, and overall delightful shopping experience. It’s great to know that you have fantastic options to explore, ensuring that you’ll find a gown that makes you feel absolutely radiant on your big day.

Get ready for a lot of screenshots but it was so helpful for me that I am hoping it is equally as helpful for you :).

Where We Went:

I originally wanted to have a big dress shopping weekend in Chicago. I’ll get to this more in the “what I wish I knew before dress shopping” section below, but basically, because I had a decent amount of people I wanted to come with me dress shopping, the Chicago idea got squished real fast.

The Milwaukee dress places allowed for large(r) groups, so we did one day of dress shopping in Milwaukee and one in Chicago.

Here’s what our exact schedule was (and then I’ll say what I would change about it):

Friday:

12:00pm: Miss Ruby’s Bridal Boutique (Milwaukee)
2:00pm: Lunch at Blue Bat (across the river from Miss Ruby)
3:00pm: Strike Bridal Bar
6:15 Dinner Reservations at Screaming Tuna

Saturday:

Morning: Drove to Illinois and went shopping at Oak Brook Center (best mall on the planet)
Got lunch at Sweet Green
1:00: Bella Bianca Bridal Couture in Oak Brook, Illinois
2:30: Bridesmaid Dress Appointment at Bella Bridesmaid

Overall, our schedule really worked nicely, but there was a few things I would have changed.

We started at Miss Ruby’s which was honestly the perfect place to start. Our consultant was amazing and so great to work with! Everything in the store is under $3,000 which was really fun because I basically was able to have free reign. The ONLY thing bad I have to say about the store was that I know so many people that go here. I was really worried I was going to see the dress I picked out at someone else’s wedding I knew. That’s a high-maintenance issue of my own I’m working through and everyone thought I was ridiculous saying that so…personal issue.

We did eat before our dress appointment, but we were ALL starving after that first appointment. It doesn’t seem like trying on dresses would be a tiring event but IT IS. We were almost hangry :/.

My advice to you, if you book a noon appointment, is to make sure you have a food place picked out for afterwards; this also makes it fun because you can debrief what your thoughts from the first dress place.

Strike Bridal Bar is where I ended up actually buying my dress. They only allowed you to bring 4 people with you (this was standard amount), but for $75 you could bring six and have a “VIP” treatment. The experience was actually super fun and I highly recommend. They had drinks and macarons for us. I had Ben’s mom and my best friend Lauren come so I was able to pick out my dress with everyone there! I loved their setup because they basically had curtains that closed right in front of everyone so when you opened the curtains and was like a “wow” factor.

They had one designer there that I LOVED. The only dresses in the store that I was leaning towards was from that designer. I think if they didn’t have that designers collection(s) I would have had a hard time finding something I loved.

When I actually picked the dress, we did a whole confetti pop and it was really fun. Our consultant stayed late with us and just really made it a memorable experience. She also dealt with me trying on two different dresses like four times each…I literally left the store with a deal that I had to call the next Monday by 5:00pm telling them which dress I ended up choosing. I could not decide for the life of me between two dresses which one was “the one” and she was very patient with me haha.

ALSO! They had a decent selection of plus size dresses which was awesome to see!

I got reservations at Screaming Tuna (my fav restaurant in Milwaukee that happens to be a block away from Strike Bridal Bar). I made the reservations for 6:15, but it would have been perfect to have them at 5:45-6:00 instead.

That sums up our Milwaukee dress shopping adventure. We headed to Chicago the next day!

We went to Oak Brook (45 min outside of Chicago). This is where my favorite mall ever is so we spent the morning shopping. I had already had an appointment booked at Bella Bianca and they have a 24 hour cancellation policy. Since I found my dress, I called to cancel but it would have been $50 (I think) for a cancellation fee (this makes sense – not complaining about this). I didn’t want to cancel my appointment and pay that fee so I asked if we could turn the appointment from a dress appt to an accessories appt. This ended up working out perfectly because they had such an incredible selection of veils AND I got my earrings for the wedding. Warning for this place – The most insanely beautiful dresses but definitely the priciest bridal boutique. I would have DESTROYED my budget here haha.

Next door was Bella Bridesmaids. This also worked perfectly and my sisters were able to try on different bridesmaid dresses.

We really checked it all off the list and it ended up being an extremely successful two days!

This was runner up dress…honestly, prettier in person but this was like in person. NEVER thought I would go for sparkly like this but I loved it!! It had sleeves too which I would wear for the ceremony and take off for the reception.

Everything I Wish I Knew Before Wedding Dress Shopping:

In Chicago almost all dress places had a strict 3 person limit. If you wanted to have more, they were going to charge you like $300. In Milwaukee, it was a strict 4 person limit. They would charge for more people in Milwaukee but it was like $75 vs $300 haha. This was a surprise to me and something I hadn’t even thought about. Sarah was going to fly out to go dress shopping with us and I’m so glad we waited to book all of this because she wouldn’t have been able to come anyways haha.
Speaking of booking…BOOK APPOINTMENTS EARLY! This was another thing I didn’t think about. I waited way too last minute to book appointments. If you can, I would definitely recommend booking your appointments at least a month early. I booked everything two weeks before and there were some places I couldn’t get into because of this.
Eat!!! The hanger is real. It’s weirdly exhausting trying on dresses and to mix that with hunger is a breakdown waiting to happen.

Bring a flower bouquet. This was something I would have never thought about, but Aunt Bett and my matron of honor had one sent to me morning of dress shopping. It was such a cute surprise and really completed the dress look when I was trying them on!
You’re going to be naked all the time. Wear cute underwear and nipple covers.
Apparently it takes like 8 months to get dresses in. I don’t know if they tell you this to just close the deal, but I guess I was pushing it close with my wedding date (June 24th wedding and we went dress shopping Aug 12 the year before).
Every place we went was able to really customize the dress. I didn’t realize there was so much flexibility with this but you really can basically customize anything you want on the dresses!
Wear cute earrings that you’d want to possibly wear on your wedding. I have these $1 (literally) earrings from SheIn. I bought a nicer version for my wedding day but they’re essentially the same thing. This made it look so much more official and really did make a difference!

I think that wraps up all the things about my dress shopping weekend!! I am a terrible bride and way worse at planning than I thought I would be. But, I have to say, dress shopping was the most fun I’ve had thus far during the wedding planning process. When I found my dress I kept saying how sad I was because I’ll never do this again hahaha (already planning my 10-year wedding vow renewal JUST so I can go dress shopping again.