Do Stylish People Hire Personal Stylists?

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Next month I am attending a conference for rewardStyle, the main platform I use to monetize this blog. Most of the links and those little carousels of the items I'm wearing are created through rewardStyle.  The conference is invite only; 200 of their top bloggers will congregate in Dallas, Texas to attend seminars to improve their blogs, meet with brands, and side eye one another’s outfits as they sip rosé on a rooftop patio while taking selfies. I’ve been invited before and declined; friends who attended have said there’s a strong Mean Girls vibe and it can be very cliquey. However, this year I’m past being concerned with cliques. I want to learn how to blog smarter, and I know a few bloggers attending. I’m looking forward to it.

A video from last year's conference

Thing is, this conference is happening at a pretty inconvenient time. Starting April 1, I will have a new position in a new department at my company. This is a position I have wanted for a long time, so this is a good thing. However, this month I am transitioning out of my old position and starting work on the new and am working more hours and filling my brain with new information and the new ways of this new department. The last thing I have time or brainpower to think about is what I’m going to wear in a few weeks to this conference.

I also haven’t fully risen from my January slump. I feel like a robot, an assembly line going through my days without having the time to slow down and focus or even realize what I am doing. I blink and a week has gone by and I can’t recall what I wore, what I ate, where I went. I’ve gained weight, my roots need to be touched up, I’ve been using the dry shampoo more than I should, and if I didn’t have this blog or have to go to the office I’d likely be spending every day in my favorite sweatshirt with the neck cut out and knit pants. Yes, that’s what I’m wearing while typing this at 4am with a bout of insomnia. Even if I had the time to think about what I am wearing to this conference, I don’t have the motivation or inspiration.

I know what I'd want to wear, I just don’t have the time to put it all together. I realized that one evening at 11pm when I finished my blog post, finally turned off Outlook for work emails and realized I finally had time to look at the itinerary for the conference and start thinking about what to pack. 11pm. I had to get up at 5am and had a busy schedule the next day and the day after that and the day after that. Was I really going to sacrifice my sleep which would sacrifice my performance the next day to spend hours scrolling through online stores to shop for dresses? What weekend did I have free to dig through my closet?   And when would I have the time to get to a mall?  Other than the ELOQUII store opening last week I haven't been to a mall in over a year.

As someone with two jobs, a family, personal and community commitments, I regularly look at my time from an hourly wage perspective. With a blog sponsored post I break down how much I will receive and how many hours it will take to photograph or video, to write, to edit, to work with the company, etc. I’ve broken down my salary at work to know my hourly rate. I also do this with chores, tasks, and volunteer positions. I need to do this task, it will take me four hours. If I hired someone it would cost $15 an hour. Would it be worth $60 to have someone else do it so I have those four hours to do something more valuable? Which would be more valuable, me staying up all night to bake brownies for a bake sale or working an hour at the booth and donating $10? Is there ROI on attending that blogger event in Virginia? How much would I pay someone to just figure out what I should pack for this conference so I can hit the ground running with my new job?

But what about my reputation? I'm a fashion blogger for heaven's sake.  Would I be less credible if I hired someone to help me with what to wear?  But then I thought about how so many celebrity style icons have personal stylists.  Those who have a great look often have a great team behind them.  Nicole Ritchie uses a stylist.  Cate Blanchette uses a stylist.  Kerry Washington uses a stylist. Michelle Williams uses a stylist. Alexa Chung uses a stylist. Even Rihanna uses a stylist.  We all benefit from a second opinion!

My good friend Rosana is the owner and chief stylist of DC Style Factory, one of the premiere personal styling companies in DC (who now does virtual sessions across the globe). I dig Rosana, and I dig her thoughts on personal style and how she runs her business and trains her staff. I know some of you readers have used DC Style Factory – I recommend the company when you contact me asking for a stylist, she has recommended this blog to clients who have a similar body shape, and I have friends IRL who have used DCSF and been happy with the experience. I’ve always been curious about how a session with a personal stylist would be… having them help me pack for this conference would save me time, save me brain energy, and also hopefully get me out of my sartorial slump.

I reached out to Rosana, I didn’t know if she’d be cool with mixing business and friendship but she was up for the task and from the get-go treated me like a regular client (and yes I am paying for this like a regular client). She said this was Special Event Styling. She sent me a link to schedule two sessions, one at the beginning of March to review my existing closet, define my style, strategize looks, and build a shopping list. Then a second session a couple weeks later to review purchases, confirm outfits, and decide what needs to be tailored. I let Rosana know I would be sharing my experience on the blog and she is conducting these sessions and all communication in the same manner she would with any client (there’s a few random texts about earrings in the middle of our usual conversations but we’re trying to keep it to a minimum).

I felt sharing my experience may be helpful to those who have considered hiring a personal stylist but think they’re not rich enough or important enough for it. Or that they feel they know their personal style and don’t want to hire someone who will try to change them.  I also was curious; I've been friends with Rosana for years and even my best friend has used her, but I didn't know what a personal styling experience would be like.  So follow my journey as I have posts about the first session, the second session, and the final result.  And you KNOW I'll be sure to recap my experience at rStheCon (what they call this conference) – what I wore, what I learned, and who was side-eyeing my looks while sipping on rosé!

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 very interested in hearing about your experience at the rS conference. I’ve never been invited and I’ve heard mixed reviews but I’m glad to hear that you’re going!

  2. I think you raise an interesting question: what is style? As someone who lives in NYC, I see great style on the street and I can tell you it does not result from wearing the same thing everyone else is wearing or buying a new outfit every week. Style is how you put something together, even if it is five or ten years old. Looking at that video you posted, I don’t see anyone with any style, frankly. What I see are boring sorority girls wearing whatever they have been told is “in style” right now. So I wouldn’t worry about going shopping. I am sure you have plenty of things in your closets that would look great and be stylish.

  3. Congrats on the new position! Hiring a stylist seems a win-win; you free upgrade space for the new and an interesting new blog post! I look forward to you telling us about the experience as well as to what you wear.

  4. Good grief! The opening picture brings to mind a group shot of the popular kids in high school, not even college. Scary! It looks very uncomfortable to me but then I am a world class introvert.

    You know how to talk fashion so you can hold your own in any kind of fashion/styling group. In fact they can learn from you if they are willing to listen.

    I know I am doing an unfair thing by judging them on appearance, but here I go. They are all too young, too blonde, too thin, too white, too female for me to be comfortable. They really do remind me of the people who harassed me in high school.

    I was thinking that I can compete with the best of them in my field and feel confident. I will be going to a conference in a couple of weeks and I feel very comfortable in my work peer group. Thank goodness how we look is of little importance or I would be a wreck. At my conferences and trainings I’ve seen everything from conservative suits to cut-offs. Yeah, I’m sure people notice, but it doesn’t seem to be an issue for anyone. Still I would like to look professional. Your posts about “What to Wear to Conferences” have been of great help.


  5. “Would I be less credible if I hired someone to help me with what to wear?” Answer: No. No you would not. You have so much to do (too much to do!) and you are authentically you, with or without a stylist for goodness sake. Please take care of yourself (congrats on the new position) and I hope you can rejuvenate soon.

  6. Hee! The video reminds me of an SNL bit from a few weeks ago parodying “The Bachelor”, where one of the girls introduces herself, saying by way of reference, “I’m the one with most aggressively ombreed hair”. Note: I currently am wearing somewhat aggressively ombreed hair, but it gave me a huge tickle.

    I was just clicking through some older posts the other day thinking about what to wear for an upcoming wedding and was falling in love all over again with your sheath dresses from Dobbin. I sometimes feel frumpy in my sheath dress, but you don’t look frumpy in yours, ever, because you style them so well, and they fit you so well. Just weighing in as a fan and putting my thumb on your stylist’s scale in favor of Allie in a sheath dress. Anyway I think the stylist idea is FAB. I’m 44, working full time, 2 kids, 1 special needs: dude: do what you have to do to make one part of your life easier.

  7. Just wanted to let you know how much I look forward to your posts! I love your perspective on life and fashion and simply enjoy reading about your life. I am a retired Canadian gal who actually has little in common with most bloggers but I feel like I could grab a coffee with you and never have to think up something to talk about. I can sympathize with your January slump as well and all I can say is…..try to let go of the stuff that doesn’t matter because life goes by way too fast! Enjoy your conference Allie….you are an awesome blogger!

    1. It’s a different sort of thing where they only have certain clothes they offer and won’t shop for you. I know many who have used to mixed reviews. I love the concept but don’t think it would work for this event. But I am trying a similar program for plus sized women and will be reviewing on the blog soon!

  8. I beg you- do this with the bag that you’re gonna check. I read a lot of blog posts where people go off on fabulous trips with just a carry on bag. They mix this with that, they wear the same pair of shoes the whole time, they hang their underwear in the bathroom to dry out. I think if you can hire a stylist you can pay the bag fee.

  9. I wish you well at the conference. I admit when I looked at the video, all I could think was “Stepford Bloggers”. Look at their hair- they are all clones. Please don’t get intimidated. Concentrate on learning all you can, find nurturing friends, and think of how many of us are impressed with your personal style and willingness to share with your readers! Jo

    1. I’m not concerned, I can literally be the mother of many of those bloggers so I can’t and won’t compare. But I may have a couple years ago! I’m looking forward to finally meeting many virtual friends in real life and think I’ll learn a lot! Wish I had more time to explore Dallas, the only other time I was there was for work and all I saw was my hotel, my client’s office, and a Cheesecake Factory!

    2. Jetpuffed, your reaction was exactly mine!

      I read Allie’s blog for her personal style, it clicks with what I like. We are not in the same age bracket, not even close, and we don’t have the same body type, so it’s Allie’s honesty, charm AND style that wins me over.

      Go with confidence Alison Gary, you are more than enough!

  10. I am really curious about people’s experiences working with personal stylists, so what an opportunity for us readers!

  11. I’m looking forward to reading about your experiences with the stylist and the conference! What you described above (figuring out your hourly cost, pay, etc.) is what my husband refers to as “opportunity cost.” He frequently does that when making decisions for various things he’s dealing with it. I think it’s a good practice & helps to make us sometimes realize what’s worth certain effort/time/money and what’s not.

    Best of luck with your new position at work & congratulations!

  12. I would have never imagined a mean girl vibes there.. how terrible – I’d think by now we were all grown up.
    Certain that it will go great for you I am looking forward to the recap-

  13. I know you’ve been feeling “slumpy” lately, but just wanted to say I always enjoy your posts and am finding myself surprisingly excited to read this stylist series!

  14. So excited to see that you’ll be coming to Texas! I’m from Fort Worth about 30 miles west of Dallas , and if I had an event there I would probably have the same reaction you did, especially if the entire crowd was composed of fashion bloggers. Will be following your consultation journey with interest. If you need any input on dressing for our crazy Texas weather, just let me know. It’s been awfully windy so far this season and I’d hate to be on any rooftop this time of year!

    1. Thank you so much!! Sadly I’ll be rolling in and out with no time to visit, wanted to take the least amount of time off work and it is also during Em’s spring break and I want to be home for some of that. I’ll just have to return!

  15. I’ll be very interested to hear your perspective on the RS conference. I’ve been invited in the past to some of the fashion week parties but have never gone feeling like I’d be the old lady in the room. But I think there are now more of us in their 30s and 40s so I bet you’ll meet some lovely folks!

    1. There’s going to be at least a dozen of us over 40, I know five or so of us are planning to get together and I know that there’s many more from the Texas and Southwest area who went last year and likely will be there this year. This year I’m all about changing up the game, if there aren’t enough over-40 women I’m going to start the trend. I’m excited to meet so many women I’ve admired and followed over the years in real life. Now I just need to finally meet you! <3

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