On the Street… What to Wear Shopping to Look Chic and Comfortable
We know that we love to preach how NOT to buy black, but we could not help but share this Age-mazing Grandmother, who we saw shopping the other day with her over 40 daughter and grandson! The daughter was from NYC and so they had been shopping recently and bought the same shirt. Here is how they both took this simple black piece and made it age appropriate for themselves. Not only that, we have gotten many letters from you all that are asking the question, “Can I still have a more creative or funky look and not look silly?” We say,” but, of course” !!!
Here how theses gals got their hip and “funky” but casual looks:
- Start with an good quality t-shirt dress, that hits above your knees. Notice that the sleeves are on the long side, so cover arms but will still keep you cool. Also, the v-neckline is wide and flattering. If it was a rounded neckline, it would not look as hip.
- Add leggings (see or post on leggings)
- and fun flats, like these pretty pewter ones.
- Don’t forget a dramatic light weight handbag.
- If you have a thin figure, you can belt the shirt
- Add tight straight legged jeans, and the latest flats.
Here is a step by step look:

















Got to agree with you on that one! When the girls start heading south it’s time to buy a good bra. You bust show sit halfway between your shoulders and your elbow for a perky look. Check out this post we did. http://www.fabulousafter40.com/are-your-breasts-heading-south/
I’m sorry but saggy isn’t sexy.
I think the over 40 woman looks great – and if a man were asked about her bra, or lack of, or whatever, he would smile and wonder why we even cared. She’s sexy! I find many men love a smile and positive attitude and easy sexiness rather than uplift bras and traditional “sexy wear.”
I actually love the no bra look on her. If I saw her out I would think she looked together and hip. I have seen a few older women without a bra lately, I was a little taken back at first but I like the look. This is a fabulous website BTW.
Hi Davon,
Yes, we thought so too! Been seeing them all over the stores, but was curious myself on how to pull it off after 40. I love them with those straight legged jeans. Talk about comfortable and hip!!!
The daughters boot shoes are way too cool! Gotta look for a pair of those!
Definitely second the comments on a adding a good bra to the mix!! Nothing makes a woman of a certain age look her age more than big (or small) ole saggy boobs or an old worn out holster that’s not doing the twins any favors!! Always add a bra with good support and proper fit to make you look fab at any age.
Bra and a little of make up.
beautiful woman but PLEASE wear a bra!
Hi Zabka,
Yes, a good bra is essential to looking youthful!! Great tip and thanks for sharing!!
I hate to say this, but although Grandma is gorgeous, she should be wearing a bra, or go for a fitting.