Since we unveiled AI Angie in an April Fools post, generative AI has made a lot of advances. ChatGPT is one of the most popular AI chatbots, and it uses natural language processing to mimic the way a human might write text or create images. I recently asked it a few fashion and style questions and the responses were everything from brilliantly insightful to hilariously inaccurate.

I turn 55 in July, so I asked chatGPT what a 55 year old woman should wear to look stylish. ChatGPT’s response started out with this paragraph:

Style at 55 (or any age!) is about confidence, comfort, and personal expression. Modern fashion embraces ageless dressing, meaning you can wear anything that makes you feel empowered. The key is to balance elegance, sophistication, and a touch of trendiness while ensuring comfort and practicality.

This is sound advice. I love the first sentence.

ChatGPT then went on to recommend wardrobe essentials for a stylish look.

Tailored Blazers – A well-fitted blazer instantly elevates an outfit. Opt for classic colors like black, navy, or beige.

Dark-Wash Jeans – A good pair of straight-leg or slim-fit jeans creates a polished yet casual look.

Classic White Shirt – A crisp button-down or soft blouse works for any occasion.

Midi or Wrap Dresses – Flattering and versatile, these dresses work for both day and night.

Elegant Trousers – Wide-leg or tapered trousers in neutral tones create a sophisticated look.

Knitwear & Cardigans – Choose high-quality fabrics like cashmere or merino wool for a luxurious feel.

Statement Accessories – A structured handbag, a beautiful scarf, or bold jewelry can add personality.

Chic Footwear – Comfortable yet stylish shoes like ankle boots, loafers, block heels, or elegant sneakers can complete an outfit.

This part of the answer struck me as overly generalized and impersonal. Definitely not evergreen advice for all, because wardrobe essentials differ greatly between people. Relating these to my own style, the advice about Statement Accessories and Chic Footwear are bang on the money. Knitwear and Cardigans were pretty good suggestions, although it left out cotton. Elegant Trousers was an okay suggestion, although most of my trousers are non-neutral, and some are hectically patterned. I wear dark wash jeans, but white and light washes are well represented. I wear shirts, tailored blazers, and blouses, but they are bright and many in loud and big patterns. I look awful in a wrap dress.

ChatGPT wrapped up its answer by sharing tips on how to look modern and chic.

Prioritize Fit: Well-tailored clothing enhances your silhouette and looks more polished.

Neutral & Classic Colors: Black, white, navy, beige, and earth tones create a timeless and versatile wardrobe.

Mix Classic & Trendy: Pair classic staples with one or two trendy pieces to keep your look fresh.

Layer Smartly: Layering with a stylish jacket, vest, or shawl adds depth and interest to your outfit.

Choose Quality Fabrics: Investing in good fabrics like silk, wool, and cotton gives an elegant finish.

Confidence is Key: The most stylish outfit is the one you feel great wearing!”

I think this is better advice than the list of wardrobe essentials. I agree with all of the points, except the one about “Neutral & Classic Colors”. Personally, I think ALL colours can look modern and chic. Although I love wearing shades of white, blue denim, and navy, most of my wardrobe is non-neutral and colour-rich. This mix is what makes me feel great in what in what I’m wearing, which is to the last point on the list.

This was interesting. ChatGPT is amazing technology, to be sure. It’s advice can provide a helpful starting point, but it will only take you so far. Take from it what is helpful and sensible for your style, and leave the rest. Do your own thing.