I’m Almost 29, and I Still Can’t Dress Myself

Yesterday was an interesting day.

Around the holidays, I spied a deal for a session with a stylist on Gilt City and bought it.

I remember Beth writing a post a few months ago about working with a stylist for an article Washingtonian was writing about her. Her results were adorable, and I remember thinking how cool it was, so when I saw this deal with Sarah, I was psyched.

Growing up, I was absolutely obsessed with fashion. I wanted to work for Vogue when I grew up. I really wanted to win Best Dressed in high school. I loved clothes and putting them together and putting together cute outfits.

Then I went to college and packed on 50 pounds and shopping became something I HATED, especially with other people. I’d hear my friends talking about how the 4s or 6s were too big, and I wanted to punch them. Or cry. Until I moved to NYC, most of my clothes were from Banana Republic or Ann Taylor. The clothes there were nice, but safe. They fit fine (fitting well was something I thought was more than I could ask at the time), and I didn’t stand out at all, which was perfect. I was unhappy with how I looked, and I didn’t want people to notice my clothes, because then they’d notice my zaftig body.

Look at this plain, boring, awful stripe-y dress, and please don’t look at the bangs or my sunburned arms.

I remember in early 2008, when I was feeling at my lowest, going shopping with my old roommate Jen. We went to Century 21, and I tried on a pair of Seven jeans. They were a size 32 or 33–whatever the biggest size Sevens come in–and they only sort of fit. I was going to buy them anyway but was living at home without a job at the time and didn’t really have an extra $100 for jeans that barely fit. I walked outside, sat down and started bawling at the fact that I couldn’t even fit into the biggest size these jeans came in.

When I moved to NYC, I knew I wanted to change my style but didn’t experiment much because I was still uncomfortable with my body. Once I lost weight, I did start experimenting a ton with clothes. I have everything from bright Lilly Pulitzer dresses to long black t-shirts with zebras (truth.) in my closet, but I don’t know much about what looks good on me.

Sarah came over yesterday, and I was terrified before she even walked in. I knew she was going to rip my closet to shreds, and I knew that was what I paid her for, but I was still nervous.

She walked in and after talking for a minute or two, we went into my bedroom, and she started pulling apart my closet and having me try clothes on. That first second when I realized I’d just met her and realized I was going to have to get naked in front of her was only slightly awkward.

I told her that I definitely preferred classic and preppy styles, but that I wanted to dress with a little more of an edge.

Below are some of the outfits she put together for me, and why they worked on my body type.

This is my favorite outfit. It’s a Ralph Lauren plaid top that I have with ruffles down the front with jeggings and black suede booties. I always felt that this shirt was too tight, and usually wore it under a cardigan, but Sarah encouraged me to belt it, and I LOVE this look. It looks very put-together to me, and I felt so much more confidence, immediately.

A black wool houndstooth skirt with a black long-sleeved top and cardigan. My before for this outfit would have been a slightly loose sweater on top, not tucked in, but Sarah encouraged me to show off my waist. I’m most self-conscious about my mid-section, since I definitely accumulate weight there, but she convinced me I had a great waist that I needed to show off. I mean, she is the professional…

A J. Crew blouse with a black skirt and a belt. She encouraged me to wear more belts, too, to accentuate my waist and told me never to buy low-waist jeans–they don’t flatter many people.

Same skirt, different top. This top is actually longer and looser, but she told me to tuck it in/pull it up, because the long tops do nothing for me. As you can see, I’m pulling this in the back to make it tighter. I wish it actually fit like this now. Sarah said she just wasn’t a fan of this top because she didn’t like sequins, to which I say suck it. If loving sequins is wrong, I don’t want to be right.

I felt so incredibly self-concious in this, but she convinced me that the cardigan worked, that I do not actually have a muffin top, and that this sweater shows off my curves.

For blazers, she told me to pop the collar, button up and roll the sleeves up.

I had a lot of fun with this look, too–it’s kind of different from how I usually dress, but I loved it. I felt so New York, instead of the girl from NJ who lived in DC for seven years. I’m wearing a plain black shift, the sweater is actually Sarah’s (at multiple points, she actually gave me the shirt off her back to try on) and the boots are the same suede booties above.

Again, I’m holding this dress in–she loved the style but thought the drop waist wasn’t flattering, and that I should have it tailored like this to raise the waist.

Here, I have my sweater slightly tucked into my jeans and my dog sniffing at my feet. (The rest of the time she was here, he hid under my bed.) Again, she thinks I should wear things that are slightly shorter and hit at my waist, and tops with either a v-neck, like this, or a scoop neck.

This one’s blurry, but she told me to always button my blazers and wear big necklaces like this.

This was how my bed looked by the time she left, which only made me panic a bit. Emily had stopped by and kept me company while I put them all away because she’s the most awesome friend ever.

So, the big takeaways from this experience:

• I buy clothes because they are pretty, not necessarily because they fit me well. This is such a holdover from being overweight. If I could close something or put it on a top without getting 9,200 rolls in my stomach, it fit. I have a lot more options now, and I need to take advantage of this and get stuff that mostly fits me.
• Shorter shirts, less leggings, less prints, more timeless stuff.
• Button stuff up.
• I can wear tighter things than I think I can. Especially tops. For blouse-type tops, I end up going for looser ones subconsciously so that they can fit my chest, too.
• I definitely don’t see myself as overweight any more, but I don’t think I see the same body that others see. Putting together outfits that really flatter my body helped with that.
• Sarah was pretty awesome, but I’m not ready to drop the $5K on a brand new wardrobe that she suggested. Surprising, I know.
• She also wanted me to throw out a lot of clothes. As I’m sort of a packrat, and recently got some of them tailored, I’m just not ready to do that yet.

 

Would you ever work with a stylist? If your body’s changed, has your style? What’s your style like?