Outfits for Sideline Saturdays
Plus 6 real outfits I wore last week
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Do you ever stop to reflect on the choices you’ve made and how they led you to where you are today? I think about the crucial moments without which, I would be living a different life. As I kid, I would sit at the kitchen counter and sketch outfits. I would spend hours dressing my Barbies in the miniature wardrobe I’d compiled for them. If anyone asked what I wanted to be when I grew up, it was always “a fashion designer.” Fast forward 30+ years, and I’m an attorney working in commercial real estate. I’d be hard pressed to find a more opposite career path, which may be why I find it so interesting to look back and determine how I got here.
Upon reflection, I’ve determined that my tale involves two critical moments. First, a global recession. Second, a blind date with a guy from Iowa. Two pivotal events, without which, I wouldn’t be sitting here (which, to be clear, is in the bleachers watching my daughter’s gymnastics practice). Those events were like little lightning strikes, causing me to march in a new direction.
I often wonder what I would be doing if those curveballs hadn’t presented themselves. If the economy hadn’t been trash when I graduated, I may have really tried to get a job in fashion PR or marketing, which was my goal until the moment I decided to go to law school.
I met my now husband a few weeks before I left to study abroad for a semester in Paris. While we didn’t start dating until I got back, I likely would have lingered a few weeks or months if I wasn’t so motivated to return and get to know the guy that caught my eye before I left. Who knows, maybe I would be fluent in French? He also played a big role in my decision to become an attorney and has been my biggest cheerleader and motivator in my career.
I truly love my life and am fully obsessed with my husband and kids, but I do enjoy retracing my steps and playing a game of “choose your own adventure” with an alternate ending. The contrast between my prior life plans and current reality likely contributes to my passion for getting dressed. It is my favorite form of creative expression. Some paint, some draw, some write music. I get an immense sense of joy from solving for the right combination of colors, textures, shapes and scale, and polishing it all off with shiny accessories.
No, I do not work in fashion. I am not an expert. But man, do I love getting dressed. And I like sharing outfits for my real life, not the one I visit in an occasional daydream. Accordingly, this week I’m sharing:
Seven Outfits for Sideline Saturdays (outfits I wore to youth sports)
Six Outfits I Wore Last Week (mostly to work)
My husband was a D1 college athlete, and I played a lot of youth sports (although not well), so we are encouraging our kids to partake. As a result, much of our Saturdays are spent on the sidelines. We are near the end of the fall soccer season here in Arizona. Prior to each practice and game, my daughter has told me that she doesn’t want to play next year. Ok, sweetie, no problem. Let’s just finish out the season. This past weekend, she scored her first few goals of the season. The first words out of her mouth when she ran victoriously off the field were “Mom, I think I DO want to play next year.” It’s amazing how a moment of glory can inspire you!
Given how much of my real life is spent on the sidelines, I’ve curated a few of my go-to outfit formulas for Sideline Saturdays. The good news is, even if you’re not spending Saturdays in a camping chair rooting ridiculous phrases like “Way to stick with it, Grace!” or “Great hustle, Landon!”, these outfits translate well to weekend errand runs, trips to the farmers market, or a casual brunch. You know, all the things that childless adults enjoy on a regular basis.
Here are the key points I consider when dressing for youth sports:
Comfort: I’m hauling kids, snacks, water bottles, all over creation. I need to be able to move and possibly get sweaty without regret.
Sporty Factor: I enjoy a theme—it helps me guide my outfit decisions. Because I’m attending a sporting event, I like to add a sporty element to my outfit. Wind pants, windbreakers, sneakers, baseball caps, and hoodies all meet the mark.
Layers: Layers are key in AZ right now. It is cool in the morning, but quickly heats up as the day proceeds. We need to be prepared to brave the elements!
This season, my go-to look has been some sort of track or wind pants and a cropped jacket with sneakers. Plug in any type of pull-on pants as an excellent alternative to the track pants. I’ve had my eye on these from J.Crew.
Here are some options to recreate the look. Check your closet first — IMO, the best way to jazz up your athleisure is to mix in some of your normal clothes. Don’t just revert to your stack of Alo.
Another combo I love, but have yet to rock this season, is an oversized jacket over leggings with sneakers and either a baseball hat or a beanie. The oversized jacket covers your booty, which is ideal if you forget to bring a blanket or a chair. Bonus points if you sneak a hoodie underneath the jacket to up the sporty factor. Alternatives include: tying a sweatshirt around your waist (see image 1), or throwing it over your shoulders. Tall socks are a must—I’d recommend these and these. My preference is a dad sneaker with this look, but a slim sneaker works too. If dirt and grass are not of concern, I’d suggest swapping in a ballet flat or a loafer to really up the interest.
If this is not your vibe, or you’re just looking for additional inspiration, I’d direct you to Katelyn Cnossen’s post from this week where she polled some Substack royalty for their preferred sportswear:
For Floridians or if baseball is more your thing, see my previous post on little league outfit ideas:
What Are We Wearing to Little League?
Did anyone watch the TV show Girls? I remember I scene where Lena Dunham talked about how she needed to go live big life experiences so she had something to write about. That mindset held me back from writing anything. My life so far has been almost mundane. College, law school, marriage, kids. But now that I am actually writing, I find the simplest mom…
In keeping with the theme of real-life outfits, here is what I wore last week. M-F were spent in the office. My husband and I snuck out for a dinner with friends on Saturday. We were supposed to go to dinner after a pitstop to watch Game 7 of the World Series (more sports!!). We almost caved and ate at the bar because the game ran long, but I complained about wasting a good outfit on a sports bar and ultimately won the argument. We went to Pinyon, which is a new concept by Buck & Rider in Old Town. The food was great, and the location is fantastic.
Monday: If you’re not following Traci Landy, please do me a favor and click subscribe. She and I had a meeting of the minds last week regarding this burgundy and red color combo. I’ve been living in my Gap big shirts, but this burgundy stripe is my ultimate favorite. My jeans in this pic are old, but I tried on the Reformation pair I linked below in the store, and they are fantastic. Super flattering and fit TTS.
Tuesday: I instantly added these Pixie Market pants to cart when I saw then on Shopbop (and thank god, because they sold out SO fast). I’ve linked a similar pair by the same brand. I think of Pixie Market as a Zara alternative — the price points are similar.
Wednesday: The good news is that Aligne still makes many variations of the Daphne blazer that I’m wearing in this photo. The bad news is, they no longer offer it in red. This sweater is the closest alternative I could find with a similar shape and color. My jeans are vintage, but sizing up 1-2 sizes in these Levi’s would give you a very similar look.
Thursday: My husband told me I need to take this blazer to the tailor. How many times do I have to tell him that he just. doesn’t. get. it. I love black and brown together and thought the western belt added some fun flair to this look.
Friday: I’m realizing I wore a cardigan 3x this week. Cardigans are currently a hero item in my closet (cc: Kelly Williams ), and this one is my favorite. I have it in four colors. They are currently doing a Black Friday sale and offering 25% off. Code is ACTHANKSYOU25 (no affiliation, I just love these sweaters and a good deal)!
Date Night: Wearing the same brown blazer as I wore above, but this time I paired it with some very short Doen shorts and yet another cardigan. I snagged these shorts during one of their sales last year and have been patiently waiting to wear them with my suede boots.
If anyone read last week’s post, I’m happy to admit that tonight, I went to a professional event, and when asked if anything exciting was happening in my life, I told them about my Substack. That’s progress, baby! Roses to vulnerability, thorns to his response, which was, “What’s Substack?” You can’t win ‘em all, folks.
If any of this resonated with you, please hit the like button, leave a comment (even if it’s nonsense!) or share with a friend. It will help me grow.
If you’re so inclined, go ahead and follow me on Instagram at @hi_itsmejaymee for more outfit inspo and shopping finds.
XOXO
First thank you for sharing my work :). SECOND I am obsessed with those retro rider pants, they are exactly what I have been looking for! You are nailing sporty chic for your kids youth sports. I am very inspired and cannot wait until my son is playing sports (hopefully haha!).
That's so cool you wanted to be a fashion designer. It's fun knowing what people wanted to be when they grew up. You definitely have an eye for fashion and style!
I love all these outfits! 🔥