Plus Size Gingham Summer Outfit

Get your preppy on!  This plus size gingham summer outfit will have you looking so cute.

Plus Size Gingham Summer Outfit with white cropped demi boot jeans, blue gingham top, Tory Burch Miller sandals, and straw tote bag - Alexa Webb

An adorable blue gingham top with ruffle detail is paired with cropped demi-bootcut white denim.  These jeans are a modern cut, almost like a kick flare.  

Plus size white cropped bootcut jeans - Alexa Webb

If you’re not familiar with JCrew’s or Madewell’s denim sizing, be sure to check out their size chart

Below is JCrew’s denim size chart.  I included it because Madewell is transitioning to a new sizing system for their plus size denim.  But, these jeans use the old sizing.

Size Chart

JCrew Denim Size Chart

Then I added some pops of red in the statement earrings and straw tote bag.  Oh and a red Tory Burch enamel bracelet, for good measure.

I finished the look with an optional denim jacket and some classic Miller sandals.

Story Time!

You might remember from a previous post about a bad date that I sometimes tell real-life and sometimes funny stories here on the blog.

So, if you liked my last tale of a dating disaster.  Strap in for another!

Now, in that post, I said that was the only time that I, Alexa Webb, was the bad date.  But I lied.  I was most certainly a bad date on this particular occasion…

The Geography

Way back when I was chatting with a fella who lived in Canada.  He is originally from the Middle East but moved to Canada as part of a research program. 

He is a medical doctor who conducts very specialized research.  And as such was recruited by a university local to me.  So he was moving to my city.  

He was pretty nervous about the move.  He had never been to the US and all he knew of my city was what he had seen on HBO’s The Wire.

For those of you who haven’t seen it, the Wire is about Baltimore’s drug trade.  It’s a really great show, you should watch it!

But needless to say, the show didn’t leave a great impression. 

After all, Baltimore is in the top five most dangerous cities in America.  Not to mention my fair city is also known as “the heroin capital.”

The Plan

So when he had to come down one long weekend to meet with the university and look for a place to live, I offered to be an ambassador of sorts.

I told him I would take him out on the town and show him how great this city is!  I decided on drinks at one of my favorite bars, followed by dinner at a nice, but not too fancy, restaurant that I love.

Also, we would be driving through the downtown inner harbor area, which people find scenic and full of attractions.  I was really going to be showing off Charm City!

The Mistake

So I picked him up in front of his hotel and off we went!

But, when I couldn’t find a place to park within a reasonable walking distance, I decided to park in a lot owned by a local business.

Now, I have done this many times before, but only for short periods of time.

So I was really upset when after our fun drinks and dinner, which went quite well, that my car was missing from the parking lot.

The Differences

I immediately realized that I had been towed.  But when I told Dr. B (let’s call him that), he didn’t seem upset at all. 

In fact, he was confused by my frustration.  I just stood there looking at him perplexed.

I said, ok, let’s go find a taxi.  This was before the days of Uber and smartphones.

He asked me why.  Again, I looked at him, like “what the hell?”  He seemed confused.  I explained: so we can get the car. 

At this point, I’ll be honest, I’m thinking this guy isn’t too bright for a doctor.

He must have realized that things here in the US are very different because he explained…

In his city, when you are parked illegally and towed you simply call the tow company and they will come to pick you up. 

They take you to your car, which is usually close by.  And they only charge you about CAD $25.

Oh Canada, you’re so nice!

Reality Check

So I explained that no one was coming to get us. 

That we had to find our way to the tow lot which was way on the other side of town, likely in a rough neighborhood.

And that in addition to the taxi, it was going to cost hundreds of dollars to get the car back.

So we began walking towards a main street.  I should also mention that it’s cold and after midnight.

And I should definitely mention that which I didn’t explain to him, that we were going to have to go through some fairly “dangerous” areas of West Baltimore.

Now, I love W. Bmore, but I also know that there are many parts of it you don’t want to be wandering around in late at night.

This wasn’t going to be fun.

Taxi Driver

We hail a cab.  And as soon as I give the driver the address he begins a rant. 

“Is this that mother fu@#ing tow company?  You know I don’t play with those mother fu@#ers! 

They towed me once, tried to get me to pay and I said h@ll no!  That’s why I’m always strapped.”

I look over at Dr. B hoping he doesn’t understand what “strapped” means.  LOL.

He has a very concerned look on his face and I’m pretty sure he knows the driver is talking about carrying a gun.

I took his hand to offer some reassurance.

But now we’re on our way to the westside as it’s approaching 1 am.

The Westside

We pass block after block of vacant and boarded up rowhomes.  Much of the westside was decimated by redlining and segregation.

We go through a “blue light” section.  Dr. B asks about the lights. 

I explain that the blue lights in Baltimore signify that police monitor the area via surveillance cameras.  These areas are considered “high crime” corners.

I didn’t have the heart to explain to Dr. B that once we’re beyond the blue lights we’ll be in places that no one even cares enough to install cameras.

Our driver chimes in.  “You know where you’re going, right?  Do you have GPS?  I don’t want to just leave y’all out here.  It’s not safe.”

I reassure him that I know where I’m going.  Dr. B seems to be holding my hand a little tighter.

The Lot

Once we arrive at the tow lot we approach a trailer to pay and get the car. 

Of course, they only take cash. 

I don’t have cash.  The lot attendant points to an ATM.   But as I am reaching for my ATM card, Dr. B offers to pay and heads toward the ATM.

This is truly a low point. 

I really didn’t have the $300.  If I spent it to get the car I wouldn’t have a working phone next month.  Money was very tight for me at the time.

So I accepted.  I cringe to think about it.

Dr. B pays and now we’ve got our wheels back!

The Ride Back

It’s now approaching 2am.  We’re finally heading back towards downtown.  Once we get to a major road we hit our first red light. 

I slow down but roll through the light.  Dr. B in a panicked voice exclaims “what are you doing?”

I then explain that when you’re in certain parts of town in the middle of the night it’s unsafe to sit at a red light.  

So, we rolled through several red lights and I could tell that Dr. B had reached his limit.

We finally make it downtown. 

I want to point out some of the tourist attractions, like the Inner Harbor and Aquarium, but I figure that’s pretty silly at this point.

The Debrief

We get to his hotel.  I can tell he’s stressed and exhausted.  Not to mention several hundred dollars poorer.

I apologize profusely.  I ask if he’s ok.  But, really, what can I possibly say? 

I basically just took him on a midnight tour of The Wire, live!  It was his actual worst nightmare about coming here.

I mean after this night, I was surprised that he actually went through with his move.

So, would you say that I was the bad date?

If you want to read more of my real-life stories, please let me know in the comments below.

Plus Size Gingham Summer Outfit

Plus Size Gingham Summer Outfit with white cropped demi boot jeans, blue gingham top, denim jacket, Tory Burch Miller sandals, and straw tote bag - Alexa Webb

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21 thoughts on “Plus Size Gingham Summer Outfit

  1. That’s the funniest story I have read in a long time. Try getting food poisoning from lunch then when the guy leans in to kiss you. You throw up all over him. That’s my worst story and it was a blind date.

  2. I follow you on Pinterest but I would like to save these individual emails, how can I “pin” or dave these- any suggestions?
    Thank you

  3. Love the gingham shirt and outfit! It’s fun! While I prefer the short sleeved, I’m glad to see you provided a long sleeve option too for those in cooler climates.

    Enjoyed hearing your dating story. I would have raised a red flag if he was suddenly getting recruited by a local university after he started talking to you. At least he paid. lol

  4. Nice outfit, funny story! I totally understand, because I live in Baltimore too. I didn’t realize that’s where you hail from. I was just interviewed on a podcast called “Living Visibly Over 50+” and listed you as a favorite blogger.

  5. Love the gingham top/white pants idea. And your stories are the best!
    I am from a big city too and have lived in a rough neighborhood. l can relate to scaring a date Valerie. Does that make you bad? I say no, your heart was in the right place.

  6. Hi there! I loved your story! No, you were not the bad date. It started out well, and then circumstances….happened. I’m glad that Dr. B was able to bail out the car, and that you both were ok. Well, I’m sure his blood pressure was a tad high, but, he was ok!

    I will look forward to more of your life stories.

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