i wish that i knew what i know now (fashion confidence)

if i could go back and give my younger self some advice, it would be this:  be bold, be strong, and don’t be afraid to step outside the mainstream and make your own rules.   after all, how much time did we spend in our youths feeling insecure?  afraid to speak up and voice our opinions?  how many of us were paralyzed by the potentiality of being wrong? struck by the fear of articulating an unpopular position?  how many of us have daughters or granddaughters that are currently struggling with these insecurities?  so let’s all throw on a fall glen plaid jacket and a pair of suede pumps and remember, “be bold and mighty forces will come to your aid.”  

as any woman of a certain age will tell you, age begets wisdom, and wisdom begets confidence.  it’s one of the perks of getting older, really.  and as any woman of a certain age will tell you, none of this can be rushed.  a 42 year old can’t transfer to a 22 year old the wisdom and knowledge a successful, mid-life career change brings with it.  a 64 year old can’t make a 34 year old understand the tears of pain and joy raising three children brings with it. 

but what we—the older generation—can do is this:  we can tell our daughters—our granddaughters— it’s OK to be bold.  it’s OK to be confident.  it’s OK to take risks.  it’s OK to make your own rules in this crazy, mixed up world.  because—and here’s the secret—everyone is makes up their own rules.   and if we, as woman with wisdom, are not afraid to instill confidence in our children, then conversations like this will become the norm.  

you want to leave your job as a lawyer and open up an apothecary?  do it!  

you want to forego college for an apprenticeship as a chef?  i’m behind you 100%!

you think your team at work could improve if they just tried this?  tell them!  

when i was younger & now that i’m stronger

last week, we talked about self-expression through style.  a lot of you reached out to me over my various social channels and told me how over the years you’ve gained the confidence to take fashion risks.  so inspiring!   and as you all know, we’re no strangers to those sorts of risk over here on the blog.  yesterday, we showcased flared jeans, last week a skirt and knee-highs, and a few weeks ago, wide-legged jeans.   

blazer (Ann Taylor) | sweater (Everlane) | similar denim (J.Crew) 

but today, i’m showcasing my go-to style:  modern preppy.  it’s a fashion sense i’ve developed over 50 years.  and to me, nothing says “bold” and “confident” more than a blazer and a clean pair of denim.  whether i’m headed to a meeting or just grabbing drinks with my daughter-in-law after work, i trust in the style i’ve worked my entire life to develop.

breaking all the rules & suede pumps

oftentimes, when we think of “breaking the rules”, we think of societal rules imposed on us either implicitly or explicitly.  but sometimes those rules are self-imposed.  whether they be fashion rules, or professional rules, or general how-i-live-my-life rules, it’s always good to step back and reevaluate how and why we do what we do. 

shoes | shoes (similar Ann Talyor) | handbag 1 | handbag 2 | handbag 3 (similar)

what fashion rules do you live by?  and are they worth breaking? 

fashion confidence with age 

depending on the year; depending on where i’m living; and depending on who i’m with, modern preppy may be “in” or it may be totally “out”.  doesn’t matter to me, though.  it’s my go-to, and i’m sticking to it.  i might spice up my style with frayed denim, a pair of suede pumps (but see also) and a statement bag (but also here and here).  but i’ve been shopping at Ann Taylor and J.Crew for years.

blazer (Ann Taylor) | sweater (Everlane) | similar denim (J.Crew) 

alright, gang!  the week is in full swing.  i hope you played hooky yesterday and are fully rejuvenated.  we’re gonna need it, as we’re heading into the holiday season.  now, before you go, let me know in the comment section one piece of advice you’d give to your younger self.  i’m not a big believer in regrets.  but i am a believer in learning, growing, and evolving through the ages.  what words of wisdom do you have for the next generation of women?  

Beth Djalali

is the Founder and CEO of Style at a Certain Age. She writes Sundays-Fridays on all topics ranging from fashion, health, wellness, home design and more.

She’s 65, 5’8, and size 8.

See author's posts