My bf and I have an ongoing bicker about what I should wear. When we pass by a Bebe store, his eyes light up as he turns to me and says, “you would look hot in that tiny dress”. I usually laugh and tell him I’m not 21 anymore and walk into the next store, usually Banana Republic or Loft. I’m a big believer in age-appropriate dressing. A tight bandage skirt with a flowy top is totally cute on my stylish little cousin who is in her 20s, but not so much on me, I’m 35…and proud. However, today I was faced with someone that did not share my views on this. I was in the subway when I saw a woman accompanied by a teen who was probably her grandson…I hope. She was probably in her 50s wearing a black shorts suit with knee high velvet flat boots (the shorts were really short but she had on sheer tights). She added an orange bag for a pop of color and her makeup and hair were well done. She seemed like a very poised lady and she looked GOOD. I was taken back by this look as I entered the subway in this outfit. I couldn’t stop thinking about this all day, which begs the question, do you believe in dressing age appropriate or does anything go as long as you look good? I would love to hear your comments!