I Asked ChatGPT How To Build a New-Year Wardrobe on $100 – Here’s What It Said
Written by
Laura Bogart
Edited by
Kristen Mae
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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.
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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