Birthday Week Extravaganza: Style thru the ages

All week I’m sharing the most important lessons I’ve learned the last 30 years. Some are materialistic, some are possibly offensive and some are decent.

Today I’m sharing what I’ve learned regarding clothes.

Apparently I’m a slow learner.

I can tell what looks good/bad on others, but I’m not as gifted at identifying the good/bad on myself. My hope for my 30s and beyond is that I will be more conscientious of what I buy and wear.

One bad habit is that I’m a bulk shopper — if I find something I like, I buy it in every color.

Loving a style and then sticking to it is something I’ve done since elementary. Here are three first-day-of-school photos that show my fashion trend (‘trend’ as in ‘what has happened,’ not as in ‘popular/attractive’).

picture4There are so many things making me laugh here. My brother and his amazing color-blocking skills, my brother’s super skinny legs and massively wide shoes and, probably the best, my brother’s facial expression and clasped hands. He’s either an evil doctor or a welcoming doctor, like, “Hello, so good to see you, so happy you could stop in today.” You can say that in either an evil doctor voice or a friendly, welcoming doctor voice — it works both ways.

OK, on to me.

So I’m clearly loving my Umbro shorts and sleeveless tee. I kept the color combo simple and classic. I stuck with a clean look and perfectly tied bow in front.

New year, new Lindsey style — somewhat.

picture5Here, I’ve decided to stick with the Umbros — seriously, who doesn’t love a forgiving elastic waist?! But I went a little bold with the color combo, and I’m a little sloppier (over-sized tee, not tucked in, bow not tied). My brother has apparently kicked his sporty side to the curb and has decided to sport a menagerie on his shirt.

Now things have really taken a turn.

picture6I stuck with all the wrong things (over-sized tee), and added hideous pieces (gold chain necklace that I’m pretty sure was a ‘mood ring’ style charm in the shape of a cat; acid wash jeans — ick!; and black Nikes). My brother has clearly given up on life and is wearing geranimals-like clothing that you can mix and match. He’s also had his eyes closed for the last two pictures — I would too!

Notice the identical bangs and ponytail preferences every year.

My problem is the time it takes me to pinpoint what isn’t right about an outfit. Sometimes I’ve purchased things because they were popular with a particular crowd I was trying to fit into. For example:


Punk/alternative: Etnies sweatshirt that definitely wasn’t flattering and a DC beanie. Nothing was attractive about this, yet I wore it three times a week my freshman year of college. Oh, and I really liked beanies:

jimmy-fallonTechnically this was part of a costume where my roommate and I performed Jimmy Fallon’s “Idiot Boyfriend” during some kind of lip syncing competition freshman year, but that white Nike beanie was something I wore at least four days a week. Minimum.


Thrift store: I bought this yellow baseball jersey and, again, probably wore it at least once a week, every week, my sophomore year of college. As you can see, still rocking the horrific bangs and ponytail look. My brother’s style has also changed — ha! That hair styling is my handiwork, but the way.

So, if I recreated my first-day-of-school photos with my styles from the last few years:

  • We could make a few minor updates to my hair: side-swept bangs and either loose curls or poorly scrunched hair that’s trying to look like beachy waves. Someday I’ll figure that out.
  • In the first photo, I’d probably wear something too tight that I bought because I thought I’d lost weight and looked OK on me when I was standing up straight.
  • The next year, I’d probably overcompensate for the too-tight look of the last year and wear fitted pants but a relaxed, slightly-oversized button-down shirt.
  • This year, I’d wear white chino shorts (from Express!) and a slightly-fitted but relaxed button-down chambray shirt (I’m seriously in love with Gap’s boyfriend shirts right now) and my favorite bubble necklace from Ily Couture.

I’m trying to pay attention to the fit of things, but again, I seem to be a slow learner and usually realize something doesn’t flatter me after I’ve worn it 10 times. But I’m sure all that changes after you turn 30, right?


8 thoughts on “Birthday Week Extravaganza: Style thru the ages

  1. now that I have a phd, I think it’s fair to say that I am, in fact, an evil doctor. we should have seen this coming… and speaking of “seeing” things, you clearly missed that every year had a theme, sisterq. the theme for #1 is “creepy”, #2 is a “show us how you really feel” (“disgusted” and “confused”, respectfully), and year #3 was “match the chair”. it’s also fun to see how you went from “happy” to “angry ~punk” to “happy punk” and then to whatever it is that you are in that prom picture of mine. I, on the other hand, am consistently cool throughout…

    and for the record, the above photos of me serve as examples of why I don’t post pictures of myself on facebook 🙂

    • Thank goodness you made us take these pictures every year! I can tell by our facial expressions that we may not have appreciated it at the time, but I’m loving it now!

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