Figuring Out How To Dress

I am twenty-nine (and still getting used to saying that almost a month later), and I am figuring out how I should be dressing. For the record, I do know how to dress myself. But I am now trying to navigate the treacherously unusual waters of dressing a smidgen older. It’s not easy when the only stores in a mall you can shop in cater to three types of women (and I will give examples):

  1. Teenagers-Such stores would be: Forever 21, Rue 21, Hot Topic, Wet Seal, Styles 4 Less (which I used to shop in as a sixteen-year old in 1999 while growing up in SoCal), and American Eagle.
  2. Older women (and no matter what I do, someone will be insulted)-JC Penney (which does occasionally have nice clothes that translate well for people my age), and Sears (I used to shop at Sears).
  3. The Corporate Urbanite-NY and Company, Express, G by Guess, and Macy’s. The Corporate Urbanite is a woman who dresses up for every occasion. If she does wear jeans, they’re of the highest caliber, and don’t really look like jeans. She loves crisp dress shirts and dress pants. For the record: I have no problem with any woman who wears these things. They usually make me feel inferior with how I dress, and I dress nicely.


Ever since last year, I have been trying my damnedest to look a little closer to twenty-nine. I go into Forever 21 and Rue 21 trying to find basic pieces that you can add to other clothing to lessen the look of teeny-bopper, but I always come out looking seventeen. My youngest sister is seventeen, you see where the issue lies.

I went into American Eagle Friday night with my parents (yes I am lame and still live with my parents at 29), where my parents very nicely bought me a new pair of jeans and some tops. The salesperson at the counter asked if we were buying school clothes. As well as making me feel like crap for being unemployed and being seen at my age shopping with my parents, I also was reminded that I don’t look 29.

Here are some things that have come with growing older in the fashion department, as opposed to when I was a wee sprig of a teenage dork:

  • I will NOT buy anything with holes in the knees, bum, or around the pocket area. My dad wonders why, and I think it’s just in poor taste, at least for me. Some people older or the same age as me can pull it off, I just find it distasteful. If there’s a little fraying on the bottom hem of the jeans that looks like normal wear and tear, I will buy them.
  • Graphic tees basically for me now are bought for sleepwear. As a teenager and in my early 20s, I’d have no issue going out in public with something emblazoned across my chest. Now, it’s got to be some political message or for a bachelorette party. I am particularly interested in owning one of these t-shirts.
  • As for dresses, which I suddenly have fallen in love with over the last year, they need to hit my mid-thigh. Which if you shop in teen stores, is a very hard thing to find. I love my legs, but there’s a fine line between cute/sexy and just slut for my tastes. I am not Britney Spears, I can’t pull off a mini dress without being very self-conscious.


As well as those examples, there are certain styles of tops I cannot pull off. I can never wear a backless dress or top, because of being large-busted. I have to wear a bra when I wear clothes, it’s a law. In fact the only time I am not wearing a bra is when I am going to bed or lying in bed, sicker than a dog. My mom has yet to realize this is a reality, when my sisters and I all have larger busts than she does. She’s getting it, but it’s been a long journey.

I just got a striped 3/4 sleeve sweater from Old Navy (I pick and choose pieces that will have long-term appeal), and a pair of knee-high boots. My youngest sister has been trying for months to get me to wear boots over jeans, legging, tights–whatever. I’ve been hesitant because of my hourglass shape, and never having the right things to wear with them. After experimenting with dresses and leggings, we tried a final combination of my only pair of skinny jeans, the striped sweater, and my boots. I come out, thinking she’s going to shoot this down, and it was the opposite.

“Wow…now you look your age.”

When your youngest sister tells you that you dress too young, you know something’s got to change. The only trouble is, how do twenty-nine year old’s dress? I have looked at female celebs who are the same age as me for fashion guidance, as well as ones close to my age, but I am still lost. At this point, I go into whatever store I go into, pick out classic pieces (as well as a few on-trend pieces), and pair them with clothing I already have.

Am I on the right track? Or is there some secret out there that other people on the verge of their thirties or have already entered their thirties that I have yet to discover?


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