5 Reasons to Shop with a Personal Shopper—with tips to make it a success

Vince Theodore of Bloomingdales

I think clothes are important. When I feel good about what I wear, I’m happier, relaxed and feel more confident. But creating a flattering, functional wardrobe doesn’t come easily to me. I wander through stores, poking at racks, trying on an item or two with no clear plan. When it comes to shopping, I need professional help.

I’m in Chicago this week, so when Vince Theodore, the personal shopper at the Michigan Avenue Bloomingdales store, gave me a heads up call about the “Buy More, Save More” sale, I booked an appointment. I’ve now shopped with Vince three separate times (last Spring, Fall and now) and not only has it transformed my wardrobe, it’s changed the way I feel about myself. Here are the benefits I’ve found from using a personal shopper.

1. Saves Time and Effort

A stylist will help you find a single outfit or many. This time I wanted to update my everyday spring/summer wardrobe for Chicago because my Florida clothes don’t always translate to city living. I arrived to Bloomingdales at 11am and was greeted by Vince with a big rack of clothes he’d selected for me to try on in a roomy private dressing room. Vince knows all the merchandise in the store. I didn’t have to wander through racks of clothes, checking price tags, hunting for sizes, or putting together outfits. He did all the legwork. By 1pm I’d tried on everything, with Vince dashing off to get different sizes and coordinating styles as needed. I ended up choosing a tight selection of comfortable, flattering pieces that work together. Two hours to update my spring/summer wardrobe—what a breeze!

Here are some of my purchases. The overall look is a clean, neutral palette in relaxed fabrics and modern shapes.

2. Cost Efficient

It sounds like an extravagance, but using a stylist can help you get the most from your clothing budget. Although independent stylists do charge for their services, most department stores—like Bloomies, Macys and Nordstrom—offer their services for free. A stylist will work to maximize what you buy while staying within your budget (do set one) and make sure you take advantage of all the store’s sales, discounts, and reward programs. They’ll often be able to provide perks like free shipping and alterations as well. I spend more money with Vince than I would on a solo shopping trip, but I wear all the things I buy, feel great in them, and I’m less tempted to to pick up random “stuff” throughout the year.

Here are some outfits from my Spring 2022 shopping trip with Vince that I’ve been wearing the heck out of:

3. Elevates Your Style

A personal shopper can help you expand your wardrobe by suggesting trends and designers you might not normally wear. They have a bigger vision for your look than you do—it’s a great opportunity to experiment. I tried on plenty of things that didn’t work out, but I ended up buying a couple pieces that I wouldn’t have thought to try, like the printed green shorts and bold pink jacket pictured below. It’s so nice to have a professional opinion in the dressing room. I love when Vince says “nope” or “it doesn’t do anything for you” because I know he wants the best for me and will help me find it. I can explore new aspects of myself and have confidence in my purchases.

4. It’s Fun!

Shopping alone can be awkward and intimidating. Shopping with friends can be feel scattered and rushed. Shopping with a stylist is the best! It takes all the hassle out of shopping and provides a creative, supportive, relaxed experience that’s all about you—what fits, flatters, and excites you. It’s the grown up version of playing dress up.

5. You’re Worth It

Look, not everyone needs a stylist. If you adore shopping, know how to find clothes you love or just don’t consider clothes a big priority, give it a skip. But if you yearn to amp up your wardrobe, express a new side of yourself or rock a special occasion, a personal shopper is an excellent resource. I don’t want to waste time or money on things that are unflattering, inappropriate or just meh. I’m not getting any younger or thinner but, with a little help and inspiration, I can still develop my style. Working with Vince has helped me do that. Thanks for everything, Vince!

Tips for your first personal shopping experience

  • Try to get a recommendation for a stylist from someone you trust.
  • Have a specific goal and a budget in mind for the appointment and communicate them in advance.
  • Have a light snack before you go. You don’t want to feel full or bloated but you also don’t want to get hungry. This experience takes energy.
  • Bring water and stay hydrated.
  • Wear nude underwear and a camisole for trying on.
  • Bring shoes with a bit of a heel or ask your stylist to provide them in your size (everything looks better).
  • If you’re torn about an outfit, text a pic to a friend for another opinion.
  • Even if you don’t like all the pieces, try them on anyway, give specific feedback and keep at it. You have to kiss some frogs! The process is iterative and the stylist needs to get to know you.
  • Don’t feel pressured to buy. A good personal shopper wants to build a relationship, not sell you a bunch of stuff you hate.

I hope this makes the process of using a personal shopper/stylist less mysterious and intimidating. If you have used these services, I’d love to hear what has worked for you!

Here are a few other Style Challengers fashion stories you might like:

We’re Wearing Spring’s Brightest Trend—Neon

The Trendiest Dress of the Season Isn’t for Every Body

How to Find Your Perfect Jeans—with Stylist Vince Theodore

Comfortable, Stylish Shoes—Girlfriend Approved

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