Hiring a Personal Stylist - No It's Not Just for Celebs

My experience, the cost, and my favorite new fashion finds.

The $99 jeans my stylist raves about

If you drop me into a home store, I’m in my happy place. Give me a fresh stack of throw pillows or a new vase, and I’m practically giddy. But clothes? That’s a whole different story.

I like to look pulled together (who doesn’t?), but I’m very much a repeat-outfit kind of gal. My closet is full of “good enough” staples, and when I find something I like? I wear it to death. So when I started planning all the photos for my book, I hit a serious wall. I needed dozens of different outfits, each one matching a specific season, and I had no idea where to start.

A cozy sweater in January? Sure. But not when I’m planting flowers in June. I suddenly realized I couldn’t just fake my way through this with the same three shirts and a ponytail. I needed help.

That’s when my makeup artist recommended a personal stylist. And honestly? I almost didn’t reach out. I figured that was something for celebrities… or at least people who knew what “smart casual” actually means. However, I was feeling overwhelmed, so I called her.

And I’m so glad I did.

How It Worked

My stylist’s name is Heidy, and she’s based here in Chicago. We kicked things off with a one-hour closet session at my house. She had me try on every pair of jeans I owned (yes, every pair), and helped me decide what to keep, what to donate, and what I was missing. It was practical, not intimidating, and honestly kind of fun.

A few weeks later, we met at Nordstrom. Heidy had already pulled everything ahead of time, so I walked into a fully stocked dressing room—outfits, shoes, accessories, all of it. She nailed my style, stuck to my budget, and somehow made shopping feel easy.

I ended up buying about 75% of what I tried on. The best part? The tailor came right to the dressing room to make quick fixes on the spot. No extra errands, no guesswork.

From there, she sent a few online links for the last missing pieces (a sports bra, a couple of earrings, sandals), then came to my house again to lay everything out. She grouped each outfit, including shoes, and photographed them so I’d know exactly what to wear and when.

In the end, we pulled together 42 different looks. That sounds wild, I know, but when you’re shooting a book that spans the seasons, it actually made a lot of sense.

Was It Worth It?

Heidy charges $150/hour, and yes, it adds up. But honestly? It saved me so much time, stress, and those late-night online shopping regrets. She kept me from panic-buying 14 versions of the same dress, only to return all of them. Everything we chose had a purpose and a place in the book…and now in my regular wardrobe, too.

Also, she’s just the nicest human. Warm, supportive, and totally honest (in the best way). I never felt judged or awkward; I just felt supported and cared for. I even bought a gift card for Finn so he could work with her, too. He’s been meaning to refresh his closet, and this felt like the perfect way to start.

Would I Recommend It?

Totally. But not just for something as big as a book photoshoot.

If you have a big event coming up, like a wedding, family photos, or even a job interview, a stylist can help you pull together the perfect outfit without all the stress (and 17 online returns). Or maybe your closet just needs a little refresh!

The best part? You don’t have to commit to a full wardrobe overhaul. You can book her for just an hour. Maybe you just want someone to go through your closet with you and offer honest, helpful feedback. Or maybe you’re on the hunt for a few specific pieces to fill in the gaps…like a good pair of jeans, a couple of tops that work for date night and errands, or a dress that actually fits.

It doesn’t have to be a huge thing. Sometimes an hour with someone who knows what they’re doing is all it takes to feel pulled together and confident again.

What I Bought

I’ve created a folder dedicated to all of the shoes and clothes I bought for my book. You can peruse all of the looks right here, but here are a few standout pieces…

• $99 jeans that are so comfy, stretchy, and amazing. Size down! I got a size 4.

• The cutest pink workout set (top & bottoms).

• Flowy floral print dress for summertime.

• Cozy cranberry cardigan for only $39.

Want to Work with Heidy?

If you’re in the Chicago area, I can’t recommend her enough. You can check out her services here. And if you’re not local, reach out anyway, she may have recommendations near you.

I never thought I’d be someone who hires a stylist. But now? I’m a convert!