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5 Lessons From My First Personal Shopping Experience That Apply To All Of My Finances


For me, the holidays are that special time of year where all my planning and diligent saving pay off. I’m a religious budgeter with a dedicated Christmas category that I fund monthly, as well as a spreadsheet listing all the important people in my life that I’m buying gifts for and their associated dollar amounts. I have no problem when it comes to spending money on gifts — a makeup haul for my best friend back in my hometown? Done. The latest Final Fantasy game for my boyfriend? Sure!

My point is, as someone who is so comfortable opening her wallet for others, I’ve recently confronted the fact that I harbor an unhealthy anxiety in regards to spending money on myself. I earn a six-figure salary, and though I certainly don’t feel rich living in San Francisco, it’s enough to feel like I should be checking my privilege 24/7. Maybe this adds a level of guilt, making me feel morally obligated to give my disposable income away. 

If the idea of treating yourself — whether you’re buying something that costs $10 or $10,000 — makes you super stressed, then let me share what I learned during my first personal shopping appointment.

1. Remind yourself what you’re willing to pay for. In case you’re wondering why I chose the personal shopping route rather than buy clothes the good old-fashioned way, it’s because facing the crowds, digging through the endless racks, and waiting forever to check out drive me crazy. After procrastinating buying new clothes to the point where I couldn’t remove the pit smell from some of my shirts, I decided that I was willing to spend more in one sitting if it meant that all the hassle of shopping was removed. I desperately needed new attire, and I kept telling myself that the money spent would be well worth it, for my sanity’s sake.

2. Acknowledge the external pressures to spend. My stylist was wonderful during my appointment: stocking the dressing room before my arrival with possible outfits, stepping out frequently to grab different styles and sizes, and providing his opinion in a nonjudgmental way. But let’s be honest: he was earning a commission off me and doing a damn good job of it. Recognize what you’re willing to splurge on and what you’re not, and don’t be afraid to stand your ground. You shouldn’t feel coerced into overspending just because we’re all socially conditioned to please people (especially as women).

3. Keep a frugal, but open, mind. I’m not going to lie and say that I never judge people for making poor financial decisions. However, I must admit that when I was told that I could save over $100 if I opened a store card, I forced the Dave Ramsey fan into the back of my mind, and begrudgingly accepted. I already live debt-free, but it seemed stupid to pay extra just to stick to my previous principles. I knew that I was financially responsible, and one credit card wasn’t going to change that (though if having a store credit card is going to tempt you to revert to bad habits, by all means, don’t get one!).

4. Don’t look back. If you’ve done a good job being intentional with your money, then there’s no reason to torture yourself wondering whether you just made a huge mistake. As much as I might want to return everything as punishment for spending a plane flight’s worth of money on designer jeans and shoes, at the end of the day, I love how they look and make me feel. Clothing will never be my favorite thing to spend money on, but it’s still important. It’s been strongly ingrained that frugal people buy experiences not stuff, but sometimes, stuff becomes a priority.

5. Then again, nothing is permanent. I have a tendency, like many women, to think that I’m larger than I am, so in my delirious shopping fatigue, I bought a pair of 7 For All Mankind skinny jeans that seemed fine while standing in the dressing room, but turned out to be two sizes too big once they stretched out a bit. It’s a piece of cake to make exchanges and returns (as long as you keep your receipts!), so encourage yourself to step outside your comfort zone, but don’t beat yourself up if something doesn’t work out. It’s not the end of the world — or your wallet.

Three hours and about $600 later, I walked away with seven items: those skinny jeans, two tops, two sweater dresses, a versatile skirt, and ballet flats. Coming from a modest, middle-class family, dropping this amount of money on a bagful of cotton and leather felt downright bonkers to me. In fact, it’s hands-down the most that I’ve spent on clothing at one time, and $50 more than I’ve spent on clothing this entire year.

The budgeting nerd inside me knows that I could have received more bang for my buck elsewhere, but I’ve learned that investing in a few quality pieces pays its own kind of dividends over time. And in a world where time is money, having someone do my shopping for me was priceless.

Treating yourself gets easier with practice, but more importantly, with planning. As surreal as it was to spend more on clothes than food this month, I’m confident that my financial future still looks bright. Once you’re out of debt, have built up a hefty emergency fund, and put retirement on autopilot, the rest of your cash is meant for you to enjoy. Order that latte, grab those bath bombs, get that much-needed massage — your priorities are your own!

And remember that it’s okay if, at the end of the day, you still enjoy treating others before yourself. Happy holidays!

Alyssa Jarrett is a content marketing manager at yet another tech startup in San Francisco. When she’s not checking her budget or trying to make her cats Internet-famous, you can find her reviewing books and their inferior film adaptations at

Image via Unsplash


  • SN

    Wow, this was fascinating – thanks for writing this. I am so excited to finally read something by you, as you always have really interesting comments! I have literally never considered personal shopping but I can relate to your situation and I have to say you made this sound super appealing.

    Question: where did you go to do this?? Did you tell them your budget, and how good were they at helping you stick with it?

    Also, SUPER impressed that you fund your Christmas budget monthly. So another question: can I ask what your budget is? I mean, even in terms of percentage or something if you don’t want to get specific. I think I went a bit overboard with Christmas presents this year and realized that I need to plan better budget-wise.

    • alyjarrett

      You’re very welcome! I’m glad it was helpful. To answer your questions, I booked my appointment at Macy’s, but it’s a free service at most major department stores. The admin called me beforehand to get a sense of my sizing and preferred styles. I told her that my budget was between $500-$1,000, although I learned that it might be best to let them know how many items you expect to purchase, so they don’t just bring you top designers.

      As for my Christmas budget, I usually save $50 per month. I am pretty frugal and prefer to make mason jar gifts for friends and coworkers, but because next year is my parents’ 30th anniversary, I set aside extra so I could treat them to something special. I imagine that next year I’ll bump my budget up to $100 per month to give myself more wiggle room, and whatever is leftover, I’ll donate to charity (which is a separate line item on the budget).

      Hope that helped. Let me know if you have any other questions!

  • JessB

    This is a great article! I hate shopping, and also seem to have a skewed sense of how my body looks. I like the idea of a personal shopper to help with those things!
    Here in Australia, I know we have shoppers who work across brands and stores, to give more variety. I might look into one of those.

    • alyjarrett

      That would be very interesting to compare personal shopping between countries! I wonder if there is an added fee for someone to work across stores…it’s definitely worth the experience though!