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.

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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.
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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?

59 comments on “I’m Almost 29, and I Still Can’t Dress Myself

  1. Aly

    I love the outfits that the stylist put together – they look great. I am guilty of buying “disposable” items, i.e. impulse buys from Forever 21. These tips are very helpful, thanks!

  2. Olivia

    That looks like it was a neat experience! Being in college myself, I rarely ever dress up more than jeans and a hoodie, when I’m not wearing my workout wear so I can hit the gym during the day. I do have some nice professional clothes and love wearing them when I need to though!

    I like all those outfits, especially the dresses! You look great in em! ๐Ÿ™‚

  3. Kim K

    i had a stylist come to my apartment and do the same thing with me and my closet! we also went shopping together, which was super helpful. i love all the new looks, particularly the first one! hot stuff!

      1. Kim K

        @Theodora: TOTALLY overwhelmed. there were a bunch of outfits she put together that i didnt really like, but she was able to clean out my closet and make piles for keep/donate/toss that was super helpful. was a good experience, but def overwhelming!

  4. Life's a Bowl

    Great outfits and I bet you could always swap a few pieces to create a totally different look! I worked with a personal stylist once at Nordstrom when I was in middle school because I was always wearing sweats [I blame it on playing sports all day, every day if I wasn’t in school] and I convinced my momma that a fashionista would help me change my habits… I thought the experience was fun but after it was over I had similar thoughts as you did…

  5. Beth @ Beth's Journey

    The outfits she put together look so cute!! I never even thought to get things altered to fall differently even though it seems so obvious. I would just think to get them taken in to fit, but I love the idea of getting that dress tailored so it’s more flattering!

  6. LL

    Yes but where does one BUY non-low-waist jeans? THEY DON’T SELL THEM AT MOST PLACES! STILL!

    Really fun post, by the way. It’s like playing virtual dress-up! I also love your first outfit, despite not being a ruffles person…HOWEVER, I am with you on the sequins.

      1. Laura

        @Theodora: Jcrew sells higher rise jeans/pants. I HATE high rise jeans however bc I am extremely short waisted so most business-y brands (Jcrew, Banana Republic, Ann Taylor) sell pants that are too high waisted for me.

  7. Katie

    All of those looks are great! We all have little things we think about our bodies but getting an outside opinion is so helpful. You look great and you need to show it off! I’m super impressed that you took the risk and let someone into your closet ๐Ÿ™‚

  8. Nicole

    This is so cool. I can tell that you don’t see your body as others see it but it’s really amazing! My favorite outfits were the RL plaid top, the black dress with black jacket and the black jeans with the sweater.
    Question: why don’t you wear red? Did the stylist mention any colors that you should incorporate more of?

  9. Jessica

    Great post! I am also fashion impaired. My fave looks are the RL top, black dress, black jeans + sweater and that short dress that you are holding in. You look so hot in that short dress!

    You go girl. Thank you for inspiring us to get our fashion business together.

  10. Gretchen @ Honey, I Shrunk the Gretchen!

    That first look is fantastic. I totally know what you mean about having holdovers from being overweight. When I was bigger, I would buy clothes solely if they fit me at all and were even remotely cute. Nevermind fit, nevermind age-appropriateness. If it slid over my hips or buttoned over my boobs, I bought it. I would buy the same top in multiple colors for this reason, and I tried to be fashionable but never felt comfortable in most styles. I love shopping more and more as I lose more weight and can appreciate the way things flatter or don’t flatter my body now!

  11. RahelRadisli

    I really love your first outfit. Looks elegant but cosy. Very nice!

    I’d love to have a stylist anytime. But I should wait until I got my dream weight ๐Ÿ˜‰ like you!

  12. Katie

    I want one! I think I suffer from similar problems. I have realized lately that I buy things too big – and it’s not flattering. I don’t know why it took me a while to realize that since I wasn’t intentionally hiding my body. Also, most shirts are too long on me (the style and my height)! I know I should clean out my closet, but can’t seem to find new, affordable places to shop that I actually like things.

  13. Jess

    Yeaaa….I can’t dress myself either, but I really like some of the outfits she put together for you, especially that first one! It looks awesome!!

  14. Brittany @ A Little Less, Please

    Clothes are my favorite thing, ever. Since my freshman year in high school (almost 6 years ago, when I started gaining weight) I’ve been buying, or collecting, clothes that would “fit me when I lost all of my weight”. Thank god all of the clothes are still cute today, because some of them are starting to fit me! That’s one of the best things about losing weight. Feeling confident in cute clothes.

  15. Kimra

    I love this! I have this idea that my body is “hard to dress” (top-heavy, short torso, so all boob, basically), but I would love for someone else to give it a shot. I still dream about being on What Not to Wear.

    I think my style is pretty boring รขโ‚ฌโ€ร‚ย my workout gear is more fun than most of my work clothes! รขโ‚ฌโ€ร‚ย but I wouldn’t actually mind that if I could just learn to accessorize.

  16. Dori

    That is really cool and your outfits look awesome. She’d never be able to come to my apartment because I don’t have a closet. It would be impossible finding anything. Ha!

  17. Eliana

    What a great post! I love all the outfits she created for you, especially the short dress which i think looks great on you. I my self am in the process of losing weight. I have lost 35lbs and although it has been a slow process (2years almost) i am keeping up with it. I always loved fashion and when i went to school and put on almost 50lbs, it hurt that i could no longer wear my outfits. I had to give away many outfits to make room for my “overweight” cover ups. Now, that i lost the weight, i invested in new clothes but i must say that i hold back a lot because i want to wait until i lose some more. Thanks for the inspiring post!

    1. Theodora Post author

      @Eliana: Yeah–I remember it being tough as I was losing weight to have clothes that fit because I didn’t want to buy all new clothes every few months (obviously.) Congrats on your weight loss!

  18. Ricole Runs

    This is amazing, I am so jealous. I have the least style possible and always buy cheap clothes. I never know what to buy or what actually looks good and my cheap clothes wear out quick and I’m sure aren’t very flattering! I need this! But I need someone to also go buy me new clothes! For a bargain too. :-). Good for you and all you got out of it!

  19. Jennifer Adams

    YOU LOOK GREAT!!! I’m 41 (or 28 for the 13th time!) and I would LOVE to have someone come tear apart my closet!! And me. And put things together for me. I tear magazine pictures out and put them in sleeves in a binder (oh, yeah, can you say anal??!!) Because honestly I have all the pieces but I’m not always good at putting them together. I wouldn’t hesitate to get rid of everything she told me to get rid of and if I had the $$ I’d spring for a wardrobe if she went and held my hand… Is she coming to Reno, NV??

  20. Dorry

    I would LOVE to have a consultation like that. I have a friend who works at Barney’s and I’d be embarrassed for her to see my closet. I actually went through it last week and gave away 3 bags of clothes. Now my closet feels empty and I need to buy some things – my friend had the same advice for me – timeless pieces and less prints.

  21. Jane

    I love love love the first look! I would love to have a stylist over too but I just don’t even know if I have anything in my closet worth saving.

  22. Rosa Mae

    I love that you recorded every outfit. My clients sometimes get shy about taking pictures. From a stylist’s perspective, there is no judgment of people’s closets or bodies. I LOVE digging in to a messy or cluttered closet and finding the gems and helping guide people as to what to toss. That’s why I love my business! And there are ways to build a new wardrobe with less than $5K, so don’t let that hold you back!

    1. Theodora Post author

      @Rosa Mae: This wasn’t every outfit–we put together a few other ones–these were just my favorite. And I’m not sure if I plan on totally rebuilding my wardrobe, but I will definitely supplement it with suggestions she made.

      I was actually surprised at how quickly I got used to changing in front of someone I’d just met!

      It must be a lot of fun to be a stylist!

  23. Di

    I really love that first outfit! I think it’s cool that you got to have this experience. It sounds like you definitely got something out of it.

    I have a friend who is going to do something like this with me at some point. She’s really into fashion and dresses really well. I, on the other hand, have absolutely no idea how to dress myself. I’m getting better and branching out more with purchases, but I still need help putting together outfits.

  24. Liz

    I live in NYC too and basically wear all black. It’s a serious problem. I am more of a weirdo/hipster than a prep though. I had to go down to NYU to give them my transcripts b/c I am applying for grad school and decided to not dress so dark and gloomy. I put on blush and curled my hair and wore a nice bright top. When I got there the girl I gave my transcripts to had a blue mohawk and was wearing black lipstick so…yeah. I looked like a freak pretty much.

  25. Maria Revutsky

    My roommate is a personal shopper/stylist and JUST did this with my closet. I tossed A TON of things/donated/sold clothes back. I got used to shopping CHEAP (forever 21, h&M) and not investing in good quality stuff. I finally gave in and bought some designer jeans which I LOVE. I was holding off until I lost the last 5-10 pounds. But that hasn’t happened in year. Might as well dress WELL NOW no matter your size. That’s my new theory and motto ๐Ÿ™‚
    but learning how to shop/dress is such a work in progress. TOTALLY overwhelming. But it’s a fun hobby/process to beautify yourself.

  26. Nicole

    Your outfits looks great – love the first one! I have recently thought I need to work with a stylist. I have very simple/classic clothing for work (pencil skirts, button downs) and then jeans and fleece/workout clothes for my non-working hours. Nothing in the middle. I love being tall, but I feel like a tall/athletic build (i.e. swimmers shoulders) do not fit with the average/off the rack clothes/styles. Needless to say, shopping for me is always a bit of a marathon.

  27. Laura

    Catching up on lots of back posts, and I LOVE this one – what a great idea! I definitely don’t think I dress my best, and I’d love a stylist to help me go through my closet and get rid of what’s not flattering.


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