Hiring a Personal Stylist – My Experience

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my experience with a personal stylistAs I shared in my first post in this series of hiring a personal stylist, DC Style Factory informed me I’d want to book Special Event sessions – one to assess my current closet and figure out my personal style and needs for the conference I am attending, and one to look at what I ordered and create final outfits.

My experience working with a personal stylist - a review of a session with DC Style Factory by Wardrobe OxygenRosana and Marisa from DC Style Factory arrived at my house on a rainy morning. We started the meeting at my dining table, Rosana with her laptop and Marisa taking notes. Before this meeting, I emailed them the itinerary for the conference (we received an agenda with dress code for each event) as well as videos from previous rewardStyle conferences. We reviewed the number of outfits needed and DCSF recommended having more than one outfit for some of the events to have variety in case I change my mind or am not feeling a certain look. We then worked on assessing my personal style. Rosana showed me several mood boards on her laptop. These graphics featured photos of women wearing outfits that fit common aesthetics – preppy, classic, boho, bombshell, and more. We discussed how you don’t have to be just one, and you don’t have to like all aspects of one either. For example, I don’t gravitate to the traditional Bombshell look of bodycon dresses and stilettos, but I love my curves, especially my bust, and don’t mind showing them off.  I find I am more of a Classic at the office, but Urban Funky and Boho after work and on the weekends.

A closet audit with DC Style FactoryWe then went upstairs to my bedroom to assess my current wardrobe and see what I have and what I need. While it was tempting to gut and organize my closet, that’s not necessary for such a session. In fact, I think it’s better to have your closet as usual to get a better feel for who you are and how you use your closet. While Marisa and Rosana checked out the visible items on hangers and in my shoe rack, I pulled shoes from boxes on higher shelves and showed them some of my clothes folded in drawers and accessories in my jewelry armoire. No need to worry that a personal stylist will get knee-deep into your lingerie drawer; Marisa and Rosana were respectful of my home and privacy and only looked at what I directed them to open or check out.

potential outfitRosana and Marisa would pull items from my closet and ask to see them on me. We built outfits with items laid out on my bed and chair, but also on my body. It’s important to note you will be stripping down to your skivvies. I wore a molded cup tee shirt bra and a pair of Soma briefs so I was as covered as if I were in a high-waist bikini but a personal stylist has seen all sorts of bodies of all sizes, ages, shapes, and abilities.

My experience working with a personal stylist - a review of a session with DC Style Factory by Wardrobe OxygenThis is a time where you should speak up – Rosana and Marisa loved me in this outfit and while I do love it, I’ve gained some weight since I wore it on the blog and I don’t like how the top fits around my shoulders and armpits. They could immediately see my demeanor change when I put it on and knew it was a no. A personal stylist doesn’t know the story behind what is in your closet – if you have a piece that you do or don’t want to wear for a reason let them know. If a piece highlights a part of you that you like or don’t like – let them know. The more information the better to help you feel your best.

My experience working with a personal stylist - a review of a session with DC Style Factory by Wardrobe OxygenDuring all these try-ons, Marisa took notes and both of them took photos. This way when they leave they have ways to remember what I own, liked, didn’t like, and what we accomplished. We created one complete look and several other partial other looks based on what I already owned. Once the session was complete, they cleaned up my room, putting everything back where it belonged.

The next day I received a multi-page PDF Style Memo from DC Style Factory. You can click here to see it; I removed some personal information like my address but left all the content provided by DCSF. This document recapped our session and gave a general idea of what I needed to add to my wardrobe to complete all the looks for the conference.

Two days later, DC Style Factory emailed me a Google Doc with an invite to edit. Because I am so busy, and because I write about online shopping, we chose to not do in-person shopping and for me to place the orders. This doc was an Excel spreadsheet that was separated by event, then columns that had the product description (and sometimes a comment from the stylists explaining why they included it or what they could see it styled with), a hyperlink to the item online, and then a column for me to provide comments. The retailers were all ones that have free shipping and easy and usually free return policies so it wouldn’t be hard for me to box up the items I didn’t like and send them back.

While there were retailers I know well on the list (hello Nordstrom, ELOQUII, and Boden), there were many I’ve never tried before, and from the retailers I knew, they chose brands and silhouettes I wouldn’t normally consider. Some I clicked on and said, “aw hellz naw,” and because I am a fashion blogger, there were a few I clicked on and said, “I’ve tried that already” or “I know how this brand fits me and this will be too big/too small/just right.” Many I clicked on and was intrigued or excited. Some were from brands I had relationships with so I reached out to them to see if they may offer items for free or reduced in exchange for having them featured on the blog and social media. I put a hurting on my credit card ordering all these items, but I knew a huge percentage would be returned, and I had already saved up for this expense so when the bill came in for the remainder I could pay it off. As I ordered items, I highlighted that row on the doc in yellow.  I used the comment column to explain why I didn't order or if I was waiting to hear from a brand.

If you follow my InstaStories on Instagram you know my orders have started rolling in. My UPS and FedEx guys are working over time; my mail woman is used to it and when we see her arrive, Karl will go out and carry the boxes from her truck. I’ve been taking selfies of myself in the items and sharing them with Marisa and Rosana so they know what I’ve received that is awesome, and what I am immediately returning.

I’ll be honest, after my first session I felt… meh. I didn’t feel that anything was that revolutionary. Also, the Nic + Zoe two-piece dress was a look I had already considered a last resort for the black tie optional event and it concerned me that they liked it so much while I felt so fat and unstylish in it from the waist up. Maybe it was PMS… But then after getting the memo and then the links… I was excited. They really got me, and they get what I wish to achieve. And they did all the online searching for me, saving me so much time and stress.  I don’t want to be or look like anyone else but me, but I want to be the best me. I want to look good for the conference, but these clothes are for my life beyond the conference, beyond the blog. It’s a kickstart for spring, an extension of my current wardrobe, and an update to my existing defined personal style. And while most of the items that have arrived at my front door have been returned, the pieces that I’ve kept are good. Like mega good, like where have they been all my life good.

My next session is later this week, I look forward to sharing with you the final result of all of this!

Tips When Working with a Personal Stylist:

  • Do your homework. Not all personal stylists are equal, and not all are right for you. Even the one your coworker or best friend used may not be your best bet.  Check out their websites, their blogs, their social media channels.  Are they styling only 20-something fashionistas?  Do they seem to focus on career wear?  Do they ever work with plus size women, or older women, or those with special needs or situations?  Most stylists have reviews and testimonials, while they of course feature the best ones these are still a great way to get a feel for the stylist and if his or her style will mesh with yours.
  • Do your laundry.  You want all your clothes clean and accessible.  While you're at it, if you keep shoes or your day bag downstairs, bring them up for your session so the stylist gets an accurate gauge of your wardrobe.
  • Do your hair and makeup. I was running late that day and had only mascara and air-dried hair.  Big regret. Clothes look better when you look better; do your hair and makeup as you would every day, or if it's a special event styling, the way you'd do it for that event.
  • Wear clean underwear. Well duh, but I mean wear the bra and undies you have in the best condition, and that are the most versatile.  You will have practical strangers digging into the corners of your closet and seeing you practically naked; you'll feel more comfortable if you're in skivvies that don't make you blush.
  • Be honest. Let them know when you're not happy, when you're unsure, when you're uncomfortable.  Any decent stylist WANTS this feedback, you can't hurt their feelings, this is about your image not their ego.  Their success is when you feel great in what you're wearing.
A woman with curly hair wearing a plaid blazer holds a green fur coat over her shoulder on a city street.

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  1. I’m curious about the price list. Does that include the value of the items you already have? Or is that approximately what you need to spend? If that’s what you have to spend, it’s a big number. But then it’s really a business expense. When I think of it that way, I’m not so shocked.


    1. The price list is the top number. I’ve already gone shopping and almost every items has been found for a lower pricepoint. I also reached out to brands to see if they would comp or discount items in exchange for exposure. I can’t expense clothing, it’s not a true uniform so IRS would freak out on it, though the conference is a business expense!

  2. Very interesting! I appreciate your going into so much detail about the process. I love that the stylists are dressed in stage-manager black; it feels surprisingly appropriate.

    Seconding the love for your home decor. It looks so cozy and artsy!

    1. Thanks so much!

      And I think them dressing that way was by chance (or the gloomy rainy day); the next time they visited (writing the post now) one was in primarily black but the other was wearing a gorgeous Kelly green blouse!

  3. Ok. Loved this post. I have been trying to find more formal seperates as I attend a lot of the same events with the same people. If you ever decide to part with that Nic and Zoe two-piece outfit let me know it’s my size and I actually love it ( I did go to buy it and it’s sold out)

  4. I’m really enjoying this series.

    Totally focusing on the wrong part but I LOVE your house. Great furniture and accessories.Super cute but looks livable and not like a catalog.

  5. I like the Pineapple dress, it looks like you! The Nic&Zoe outfit never really clicked with me but it wasn’t the top, it’s the skirt. My daughter got married last year and I spent the entire Spring looking for dresses to wear to various events. I can imagine the Stylists would come in handy for events like that. You’d get your looks together and move onto the event details. I imagine you’ll get a lot more out of the conference with your wardrobe on autopilot —

  6. Well, I’ve been dreading trying to put together outfits for this thing, but you’ve inspired me to get cracking. 🙂 I won’t have time to find a stylist, but you’ve given me some ideas about how to best go about putting looks together.

    1. I was talking to my non-blog reading attorney friend last night and she was utterly confused why I’m worried about it. “You always look so stylish and dressed up,” she said. Oh, but this is a whole other animal! However, knowing folks like you will be there makes me more relaxed with what I am packing, knowing there’s a little tribe of us who have different kinds of blogs, and outlooks!

  7. What a fun and interesting post! I’ve used personal shoppers before, but not personal stylists. My wardrobe could use a bit of a jumpstart, and I know I could benefit from another set of eyes in putting looks together if for no other reason than,to just knock me out of my rut. Thanks for the inspiration!

  8. Thank you for sharing your experience with us! I’ve been considering working with a stylist and this has been very helpful in my thought process.

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