How to Successfully Work with a Personal Stylist

Hiring a personal stylist and shopper can be an intimate experience. You’re inviting someone into your wardrobe and revealing the mentality behind how you put yourself together each day. There are numerous studies that discuss a person’s psyche and the connection it plays in how they portray themselves to society. Most often it’s a subconscious effort, however, most of the people I work with are forced to reveal the reasoning behind why they aren’t happy with the way they look. It’s a vulnerable experience for my clients and has made me realize that what I do goes far beyond finding someone a new pair of shoes. 

I chose to write on this topic not to force you to eventually take the plunge in hiring me, but to ensure that when you do decide to invest in yourself and personal style that you get the most out of it.  Below are a few things I’ve learned along the way that are vital in creating the ultimate experience when working with a personal stylist and/or shopper.

We want to help

Personal stylist don’t get into the business because they like to shop and play dress up. Yes, that’s a fun part of the job and something we are good at, but most of the stylists I know truly get into the business because they care about people and want to share the knowledge they possess to benefit others. Understand this going into your service. We are here to help you. Use us. Don’t hide anything you need help with. Tell us everything so we can do our best to fulfill whatever void you’re experiencing whether it’s as small as just wanting to be able to see your clothes in a more organized closet, or are getting over a horrible phase in your life and are ready to shine.  

It takes two to tango

Personal stylists are human and not mind readers. Going back to point one, the more you tell us the easier it will be for us to do our job. Aside from the reason for why you’re hiring someone to conduct this service, we need to know the things you like and dislike, love and hate, what you feel good in, and colors you refuse to wear. You’re not going to hurt our feelings if you tell us you absolutely hate the dress we thought you might look good in. Don’t be rude, but be honest. The more transparency you provide us, the happier you’ll be with the outcome. We are building a relationship with you and sometimes two people need a little time to build synergy in order to tango smoothly. 

Trust and Try  

Going back to the dress you absolutely hated, keep in mind it’s also our job to try to take you out of your comfort zone and into an area we hope you discover and like.  We are going to throw you some wild cards to see if they stick. Remember, we are here to help you and things will only be done with your absolute best intention in mind. Trust us and try new things. You will be surprised at what you discover works for you and things you never considered. 


Hiring a personal stylist and/or shopper is just like hiring any other service professional- hairdresser, personal trainer, house keepers, landscapers- so treat it as such.  If you’ve already decided to spend money on an area you need help in, then don’t half ass it. Would you hire a personal trainer to only help you work your abs? Or would you want a full body experience since you’re paying him or her up to $100/session? A study reveals that women are more hesitant to spend money on themselves and often feel guilty when they do. Screw that! I’ve sent out a lot of proposals to people who have contacted me and have been completely ghosted after trying to follow up a couple times. Invest what you can if it’s something you really want, but going back to being communicative, if you tell your stylist a budget you have in mind, most likely they will have another service that they can offer. Speaking of services, don’t just sign up for the cheapest one. My Digital Daiquiri is my most inexpensive menu item where as my in-person services are the most, however, it takes a special type of person to actually benefit from the online styling and shopping service and I’ve found that it’s not that fitting for some clients. Invest in what would work best for you and trust that your stylist will recommend the best package after discovering your pain points. If they are good, they will end up saving you money anyways (found a client a $400 dress for $35 and another a $370 skirt for $65) so the service ends up paying for itself. 

Whether you just need space in your closet, don’t have the time to shop, or are experiencing a new phase in your life, don’t hesitate to invest yourself emotionally and financially in something that will make you happy or ease a problematic factor in your life, but make sure you’re also giving back to the relationship so you get exactly what you need. You’re worth it.