I pride myself on being appropriately attired all of the time. I write a newsletter about it, for crying out loud. I’m good at understanding the assignment, as the kids say, planning ahead, and seeking consultation when needed. I may not be the best dressed person in the room, but at the very least, my clothes tend to be suitable for the occasion. I plan outfits obsessively because it’s fun for me and I’ve always loved shopping and clothes, but also because for much of my early adult life, I struggled to understand sartorial assignments. I arrived for my freshman year at one of the preppiest colleges in the country with a suitcase full of the clothes that I had worn to high school in south Florida. My “look” if you could call it that relied heavily on Umbro shorts (I don’t see this 90’s fashion staple coming back anytime soon), flip flops, a Benetton rugby shirt, and a swatch watch. Unfortunately for me, this was 1993 and the other freshman girls on campus were all in J.Crew miniskirts. Right around the time I graduated from college and had finally figured out how to fit in clothing wise in the D.C. area (loafers, preppy separates, skirts and cardigans), I moved to New York City for a job. On my fourth day of work, my assistant looked me up and down and said, “You don’t ever wear contact lenses or heels do you?” I scurried back to my office in shame. It was my own personal Devil Wears Prada moment. Nearly thirty years later, I am scarred from many years of feeling like a misfit and imposter. Fortunately or unfortunately I have figured things out and now find that, lame as it may sound, a great outfit gives me confidence. My clothes are my armor: a fresh blowout and lipstick help as well.
The itinerary for Parents Weekend at my daughter’s college (JMU in Harrisonburg, Virginia) this past weekend included a Saturday Tailgate with her sorority before and during the football game. For reasons I don’t fully understand, we did not have tickets to the game so I was told we would tailgate and “hang out” all day. Fine. Hanging out was my favorite thing to do in college as well. I remember sitting for hours on weekend mornings with my roommates and when we get together these days, we do the exact same thing. Sit and talk. Have a snack. Talk some more. Heaven. I loathe an overscheduled weekend itinerary. My college did not have a tailgate culture but I’m certainly familiar with the notion and as an earnest Southern Living subscriber, I’ve poured over many an article about what to serve and and what to wear when at a college tailgate in the south. I pictured a sundress and cowboy boots and when I called Daughter 1 for a wardrobe consultation, she confirmed that she was going to wear a dress and boots. Done and done.
I attended an Ulla Johnson trunk show at my favorite local boutique last week and purchased this fabulous fall dress that I thought would be perfect for tailgating. Btw can we talk about the fringe slingbacks shown with the dress - they make my heart happy. Has anyone seen a less expensive version of this heel anywhere? I’ve googled “fringe slingbacks” and there’s not much to work with.

I brought the dress home and had a moment of hesitation about whether it was too dressy. I sent a picture to my daughter and got the thumbs up so in the garment bag it went. I figured the perfect boots for this dress were my vintage turquoise cowboy boots that I found at an exquisite boutique in Bozeman a few years ago.
Saturday morning arrived and we hustled over to my daughter’s sorority house at 9:30 in the morning as we were told. A lovely spread of breakfast sandwiches, bagels, champagne, wine and beer were set out, the grills were being assembled and a country playlist on repeat set the scene for the day. There was already a crowd assembled when we arrived and to my horror, not a single person was wearing a dress. Or boots. My traitorous daughter was in jeans, a crop top, and platform sneakers and the other moms were in jeans and “JMU Mom” t-shirts. As the day wore on I noted that the preferred outfit for the sorority girls was a football jersey that hung longer than whatever the “bottom” garment was, making it look as though there was no underneath. This “outfit” was most often paired with knee high white boots.
“I think you are overdressed,” whispered STF*, a master of stating the obvious.
It would have been silly to drive back to our hotel and change and I didn’t have a backup outfit anyway. And so I did the only thing one can do in this situation and it involved champagne and a solo cup.
I made an honest effort at mingling and chatting, really I did.
A dad wearing Dockers: “Hey, great boots!”
Me (giving a champagne influenced twirl): “Thanks - I think they are giving 1980’s Dolly Parton.”
Dockers Dad: “Really? I was thinking they look like something Taylor Swift would wear.”
Not that there’s anything wrong with T. Swift but I do not wish to be mistaken for a mom dressing like a Swifty. Misunderstood, woefully overdressed, and misled by my daughter, I felt like an awkward college freshman again and I found myself too shy to mingle and socialize with the other parents as the day wore on. I’m terrible at small talk under the best of circumstances. STF was distracted in his mission to make pizza for the crowd in the pizza oven he brought from home and my social anxiety got the better of me. Around the time lunch was being served and the drinking games and dancing were beginning, I decided it was all too much. I slipped out of the crowd and into my daughter’s house where I proceeded to nap in her bed for several hours. The next thing I knew, Daughter 3 was waking me up to let me know that the party was winding down and it was time to go back to the hotel for a bit.
Back in the sunlight, I was greeted by The Parents in Jeans. Dockers dad led the inquisition. “What happened to you?” “We wondered where you were” “Are you all right?” Ugh, I am so embarrassed just thinking about it.
To be clear, I loved wearing the Ulla dress. It has a side zip which I usually hate but this one is easy (it doesn’t have to go over a side seam). It cinches the torso in a really flattering way with a full skirt, the fabric is a crisp 100% cotton, the neckline is divine, and the print is a dream. I plan to wear it again this weekend for a dinner out during Daughter 2 and 3’s high school family weekend. This will be on our home turf which is decidedly more preppy and most people are ridiculously overdressed; I’ll fit right in. And for the record, my boots are definitely giving Dolly. I will die on this hill.
Post Scripts
I have referred to Leandra’s September 27th newsletter featuring “easy” pulled together outfits approximately 417 times. Genius, all of it. How many of us have already ordered the rosette? Update: it looks like a lot of us have because it is sold out. I didn’t act quickly and am now investigating the Etsy options Leandra mentioned. I am also enchanted by the new to me Shiloh boots she styled with shorts. I’m wondering if this Etsy pair could be the look for less?
I have watched Jenny Walton’s video about how to create a 30 second updo using hair pins 416 times. I’m going to blame my hair, rather than user error, for not being able to get a hairpin to hold any section of my hair, let alone an updo for more than 12 seconds.
Caroline’s endorsement of the tucky was persuasive to say the least. I love when real people post reviews like this! Has anyone else tried it? It’s hard to imagine being at all comfortable at work all day with my sweater tucked into an “underbelt” but it’s far from the strangest undergarment I’ve tried. What a time to be alive.
Never Not Shopping
Speaking of the Ulla Johnson trunk show, I also tried on and loved the Thalia dress. It is stunning in person. The color is a dark, rich navy blue; sheer with a navy slip underneath. The only disappointment is the stupid ribbon belt. Come on Ulla?! At this price point, the belt should be better. I paired it on with this Lizzy Fortunado belt and it was a fabulous look. The Elise top was my other favorite. It would be so fun with jeans and boots.
Speaking of boots, suede, kitten heel boots are having a moment. I’m contemplating these $200 suede Sam Edelmans. My search started with the Staud Wally boots and I’ve been scouring the world wide web for the Staud version for less. I also think the J.Crew version could be a possibility, but would need to wait for them not to be excluded from promo. On principle. What’s the point of having a sale all the time but so many exclusions? Grrr. Black suede is the sensible choice for my wardrobe needs but naturally I am drawn to this vintage looking patchwork situation:

Still looking for your splash of red? How about this vintage red coat on TRR? Love!
Obviously I’ve looked at a lot of suede boots this week and these are a pretty navy blue Ralph Lauren option on TRR.
Thanks for reading!
XOXO,
Tara
*STF is my husband. His name is Steve, but at home our kids and I refer to him as Steven The Fabulous with an emphasis on “fabulous” because when his mother comes to visit, it sounds like this, “Oh, Steven the house looks just fabulous. Steven, this roast chicken is fabulous. Girls, you are so lucky to have such a fabulous cook in the house.” He is her only son.
You are so skilled at reminding me of the most frustrating or cringe-making or just overall crawl-out-of-my-skin moments of my life. I mean that in a good way! I remember showing up to what was described as a "cocktail party" for a very fancy honor society at my university (the same one in your top photo!) when I was a freshman. I wore a cocktail dress: black with a fitted bodice, dropped waist, then tiers of ruffles to the knee, my grandmother's rhinestone jewelry, including shoe clips, and high satin heels. I got there and everyone else was in drindl skirts and poufy blouses (it was 1988). I spent the whole party apologizing for being overdressed and avoiding the side eye from the older students. When I was a senior, I went to my then-boyfriend's law school halloween party dressed as one of the Robert Palmer "addicted to love" backup singers: tight short black dress, lots of eyeliner, lots of lipstick. Everyone else was in jeans and sweaters (no costume imagination at all), so I went right home to change. No wonder I'm a little scared of fashion!!! Anyway, your dress was absolutely gorgeous. Between your stunning outfit and the pizza oven brought from home, I bet you and STF were the couple everyone wanted to befriend. Also, small talk is incredibly depleting.