- - I Asked ChatGPT How To Build a New-Year Wardrobe on $100 – Here’s What It Said

Laura BogartDecember 22, 2025 at 3:27 AM

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Like many people, I’m no stranger to the slogan, “New Year, New You.” While I know myself well enough to know there’s no way I’m giving up caffeine or committing to a 6 a.m. workout every day (this night owl hits the gym after dark), there are a few things I’d like to change about myself — most notably my wardrobe and how much I spend on it.

As a plus-sized gal with a condition called lipedema, finding cute and comfortable clothes that don’t break my budget hasn’t always been easy. And while I’m fortunate to work from home, I still want outfits that make me feel my best. So I turned to my old pal ChatGPT to ask for insights into what a New Year wardrobe could look like on a $100 budget.

In theory, anyone could replicate what I did: Give ChatGPT information about their size, health considerations (like lipedema), style preferences and price range to get budget-conscious wardrobe ideas tailored to their needs.

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A Brief Overview

ChatGPT immediately shared its understanding of what I’d need in my clothes, stating that because I have lipedema, I’d benefit from “soft fabrics, stretchy waistbands, roomy fits and clothes that don’t dig into sensitive areas.” That is all true, and I appreciated that ChatGPT demonstrated a basic, accurate understanding of the condition.

The AI told me that it would focus on cozy, plus-sized pieces that would lend themselves to being dressed up. As I scanned the mini-wardrobe with mix-and-match options, I noticed a number of pieces from Walmart and Old Navy — two outlets widely accessible retailers known for affordability and inclusive sizing.

Though I’m no stranger to shopping at outlets that cater to plus-size consumers, I was definitely happy to see options at stores that are easy to find and celebrated for their lower prices.

Core Pieces for Comfort and Style for Around $100

I was impressed with some of the foundation pieces that ChatGPT suggested to me, as well as its rationale for each item — which I have included verbatim below. Though I appreciated the AI including links to each option, I do wish it had presented the price right away so I didn’t have to go digging online.

Terra & Sky Women’s Waffle Knit Pants ($11.89 at Walmart): soft and relaxed-fit pants perfect for lounging, errands or casual outings. Great if you want max comfort and gentle fabric on sensitive legs.

Terra & Sky Women’s Plus High Waist Ankle-Length Leggings ($11.98 at Walmart): stretchy, high-waisted leggings are often a go-to for comfort with lipedema; easy to pair with tunics or long tops.

Old Navy Women’s Everywear Crew-Neck T-Shirt ($8 at Old Navy): an essential basic tee, comfy and versatile (great with leggings, jeans or under a dress).

Old Navy Women’s Extra High-Waisted Cloudcomfy 7/8 Leggings ($17.99 at Old Navy): another comfy legging option, especially good if you want something light, soft and easy to move in.

Terra & Sky Women’s Flutter Sleeve Midi Tiered Dress ($13.30 at Walmart): a relaxed dress that’s easy to wear and drapes rather than clings, making it more comfortable if your legs or thighs are sensitive.

Fashion Nova Plus Size Lily Rosaline Rayon Blend Midi Dress ($21 at Fashion Nova): a budget-friendly dress option that adds a slightly dressier vibe while still being lightweight. Good for casual parties or dinners.

Old Navy Women’s Fit & Flare Long-Sleeve Crepe Mini Dress ($18.80 at Old Navy): a slightly more structured dress you can use for a dressier outing or New Year’s plans, but still fairly affordable.

Old Navy Women’s Mid-Rise Baggy Wide-Leg Jeans ($22 at Old Navy): wide-leg jeans give room and don’t compress areas, making them more comfortable than skinny jeans; cute and versatile when paired with a nice top.

Advice on Styling This Wardrobe

After listing a few smart options for me, ChatGPT became my personal stylist, offering guidance on how to maximize both comfort and versatility.

Casual/comfort-first days: “Leggings and T-shirt or waffle pants and a cozy top — perfect for lounging, errands or home days,” the AI said.

Everyday going-out or casual dinners: ChatGPT advised me to “Pair wide-leg jeans or leggings with a nice top or one of the dresses for a relaxed but put-together look.”

Slightly dressier occasions (e.g., New Year’s dinner, holiday gathering): ChatGPT advised me to go for midi dresses or fit-and-flare dresses when I needed “a feminine vibe without being too tight or body-clinging — helpful if you want comfort and style.”

Layering and flexibility: Understanding that I might want to stay warm by layering items, ChatGPT shared that soft tops, leggings and pants are easier to layer. To accessorize a dress and add more polish, I could also add a cardigan or loose jacket.

A Final Look

Given that I’m not in a target demographic for many retailers, shopping for clothes can feel stressful — especially when I’m trying to stay on budget. Fortunately, plugging a simple request into ChatGPT helped me find some practical ideas for base pieces and gave me ideas to layer and maximize them — all without overspending.

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Editor’s Note: Prices and availability accurate as of Dec. 21, 2025 and subject to change.

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