Shopping with Fictional Characters

This post is exactly what it sounds like: My top five choices for a shopping companion, literary edition. Welcome to my wildest fantasies.

I know a lot of people have a list of historical figures that they’d love to have lunch with; for example, I would love to chat with Jane Austen, Genghis Khan, Queen Elizabeth I, Shah Jahan and Anne Boleyn over a glass of Malbec or two. But I would also love to meet some entirely fictional people. More, I would love to go shopping with them.

Shopping with someone is a unique bonding experience, and choosing the right companion marks the difference between a new, glitzy, flattering wardrobe achieved spectacularly on budget, and leaving the strip mall empty-handed and with the mean reds. You need someone who will offer sound advice: honest, but tactful. The ideal companion must be patient and funny, frugal yet spontaneous, and will never tell you that the dress you’re wearing makes you look fat. Without further ado, here are my top five picks for a fictional shopping companion, in no particular order:

Holly GolightlyBreakfast at Tiffany’s

One of my lifelong dreams is to go shopping with Miss Holiday Golightly, Traveling. Holly is an excellent shopping companion because she’s perpetually on-budget. She also understands the therapeutic power of a well-stocked jewelry store like no other. Shopping with Holly, with her sparkling personality and irresistibly skewed logic, can never get boring. Also, Holly will most likely shoplift something amazing for you, or she may surprise you and buy it outright, saving it for a gift later. Just remember to repay her with something illegal, or better yet, something sparkly from Tiffany’s.

Spoken by Holly: “I don’t want to own anything until I find a place where me and things go together.”


Lily BartThe House of Mirth 

Lily Bart will take you around to all the best stores. Be prepared to put on your highest knockoff Louboutins and walk daintily through Chanel and Saks, eyeing merchandise askance and making salespeople show you their best wares. She’ll buy you a cafe au lait and a macaron from a French cafe on Fifth and gently remind you to never buy anything on a whim. Lily takes her time with purchases and is accustomed to a certain standard of living. She never settles for anything less than perfect luxury. Hopefully she buys you something, because you can’t afford that sh*t. Lily Bart will also nurture you and make sure you look like a million New York bucks.

Spoken by Lily: “Don’t you ever mind not being rich enough to buy all the books you want?” Yes. Yes I do mind, Lily.

Rebecca SharpVanity Fair

Becky Sharp understands the power of a truly eye-catching wardrobe. Okay, so you may spend all your money on garish finery and end up homeless, but shopping with Becky Sharp is worth the risk. She has a unique and provocative fashion sense, and will challenge you to try on clothes you’d never have given a second glance. She won’t lie to you to pretend something looks good, but she may lie to you about the price. Be prepared for her blunt honesty but also for her venomous instinct for self-preservation. If you pick up something she wants, give it to her. It probably looks better on her anyway.

Spoken by Becky: “Revenge may be wicked, but it’s natural.”


Emma Woodhouse, Emma

Shopping with Emma may test your patience, but the girl does have taste. She’ll tell you what to buy and why to buy it, but when her back is turned, you can return it to the shelf without her noticing. But if her choices do strike your fancy, you’ll know you’re leaving with clothes that will undoubtedly cement your social standing. And if you’re vacillating between buying a dress and not, she’ll just rip out of your hands and leave the store, taking your dignity with her. But then she’ll treat you to a Jamba Juice and a fresh helping of the latest gossip.

Spoken by Emma: “A woman is not to marry a man merely because she is asked, or because he is attached to her, and can write a tolerable letter.”

SugarThe Crimson Petal and the White

I would just faint dead away if given the opportunity to shop with the protagonist of my favorite novel. Sugar is a self-sufficient, intelligent young prostitute in Victorian London, taking every opportunity to improve her lot in life. Shopping with Sugar means making informed choices about what you need rather than what you want. Luckily for you, what you need is a brand-new bespoke wardrobe in order to convince high society that you belong. While you shop you can discuss the latest literary effort by Mr. Charles Dickens, and debate the finer points of wealth disparity in England. Shopping with Sugar is also an economic experience, given that her rich lover William Rackham will be footing the bill. You’ll leave with plenty of beribboned boots and your savings intact.

Spoken by Sugar: “Put a black dress on, take a deep breath, puff your cheeks out and they’ll mistake you for the Queen.” Wise Sugar, extolling the undying power of the LBD.

Who I would NOT want to shop with:

Emma Bovary, Madame Bovary

I would literally drain my savings account if I went shopping with Madame. Or worse, tumble headfirst into a chasm of debt, and I really don’t fancy arsenic.

Bella Swan, Twilight

Woefully devoid of fashion sense, I feel like Bella wouldn’t be the ideal shopping companion. Maybe I’d take her sister Alice along for a second opinion, or stash a head of garlic for protection.

Who would you want to shop with?

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  • such a clever post! I love it. I’d like to go shopping with Daisy Buchanan. Even though she’s kind of a horrible person, I bet she would be a lot of fun. (esp. Carey Mulligan’s version).

    • Oh, totally agreed. She would be amazing to go shopping with. I wouldn’t necessarily want to be her friend, but that’s another article entirely!

  • Oh very clever idea and I do think you are spot on with Becky Sharpe. So who would I like to shop with? Hmmm Comtesse Phedre DeLaney D’Montreave, from the Kusheline Cycle by Jacqueline Carey. As the foremost courtesan in Terre D’Ange as well as a peer of the realm she sets the bar for fashion throughout the land [and also she would be able to get me into see her couturier who is a genius as design].

    • My sister used to love those books! I always liked the idea of the mote in her eye and the conflation of pain and pleasure. Great choice for a shopping companion!