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Fuchsia wool GNW cashmere sweater with INC chocolate leather pants, layering top, booties and simple necklace for a warm timeless winter look

Dressing for family gatherings is tricky. You have to think twice what to wear to at a family reunion! This post elucidates why, points out the biggest, most common mistakes and shows how to avoid them. Read to avoid these big mistakes when dressing for it.


  1. Family Is No Guarantee for Peace Fashion-Wise
    • Social Media Aren’t the Problem
  2. Why the Trend of the Season Is Your Biggest Enemy
    • Why to Avoid Any Hot-at-the-moment Clothes
  3. Stylist’s Advice: Wear Something Timeless
    • Stay True to Your Style
  4. Not Only In-laws and Fiancés Belong to the “Family”
    • Have the Future in Mind
    • Consider the Reason for the Family Gathering
  5. Outfit for a Family Reunion
  6. Wrapping Up What Is Best to Wear at a Family Reunion


Disclosure: There are affiliate links in this post.


Family Is No Guarantee for Peace Fashion-Wise

What? Yes, seriously! Even in your own family, you have to think about what to wear at a family reunion. Everyone will take photos. They will land in a folder and your photos may be deleted after you are “not” family anymore due to a divorce. This divorce can be yours or the person’s who took the photos.

Well, this fate of photos of you is not to worry about.


post banner showing family reunion dinner



Social Media Aren’t the Problem

… even when you are covered head-to-toe by sauce. The photos that land on social media when something funny happens to you are also not a big deal either. It just happens that someone spills the gravy all over someone else. Everyone feels pity for the poor victim. Everyone finds it tasteless of your family member to post it! Even if nothing funny happens, the photos that get posted during or immediately after the family reunion are no problem too. Even when you would wear this season’s trendy look, it is trendy this season, right. Nobody thinks anything about it.

However, that’s where there is the problem!


Why the Trend of the Season Is Your Biggest Enemy

The problem may occur years later after you had worn the big trend of the year at a family reunion. The trend everyone wore at that time. The trend that in the aftermath, years later seems to be the most silliest trend ever. The photo of an OOTD that you are embarrassed to see in a decade or more from now.

Never wear the biggest trend of the season to a family reunion unless you want to land the title of the family's biggest Fashion Victim in a decade from now. #styleadvice #FamilyReunion Click To Tweet


Why to Avoid Any Hot-at-the-Moment Clothes

That new sexy Side Bow Cutout jeans from a cheap online store for $4 that shows the skin on the sides of your legs is cute for the disco now, but not on a family photo in 20 years. Recall you bought it for your vacation trip for going out. You had no intention to be the funny mommy/granny your future kids/grand-kids giggle about. Recall you never liked being the “babysitter” anyhow. Not to mention you are an introvert. Consequently, you never liked being in the center of attention and/or the family entertainer to begin with. And …

who needs the title fashion victim of the family? #familyreunion #timelessstyle Click To Tweet


Stylist’s Advice: Wear Something Timeless

Doing so avoids becoming the amusement of future family reunions when they review photos of past family unions. But stay true to your style. This means if your style is Bohemian pick an outfit that is considered iconic Bohemian style. In this case, think of the photos of Ali MacGraw or Jane Birkin in the 1970s.

If your style is Rock’n Roll, it will be wise just to go for the red jeans, studded ankle booties, tuxedo shirt, and black motorcycle leather jacket. Leave the trendy skull scarf, and the It leather jacket with studs and chains all over the place at home.


Style blogger over 40 donning in an outfit showing timeless style
Zoom-in on timeless look
style book author in a timeless winter outfit suitable for a family meeting
Outfit details: Orvis classic Irish riding jacket with corduroy collar and pocket details, INC chocolate brown leather pants (similar here), Clark booties, layering top (similar here), GNW wool cashmere sweater and minimal necklace for a timeless winter look



Stay True to Your Style

Why should you stay with your style and not just wear something classic like Michelle Obama? You want to feel comfortable in your clothes, because that is key to come across confident, and honest.

See the outfit example in the photo above. Leather is part of my personal style. It’s a big trend at the moment too. I went for a piece in a classic cut and added other timeless pieces. I even paired it with one of my favorite colors! PINK! More on how to wear pink over 40.


Not Only In-Laws, and Fiancés Belong to the “Family”

Sending the message of being confident and honest is especially important when the gathering is the in-laws’ part of the family. You want to be regarded as the best catch s/he could get, the best that ever happened to your spouse, and as such, as a great addition to the family. Nobody wants to settle for being the “appendix“.

Even if it’s not your family, but your significant other’s, think about what you wear to your boyfriend’s family reunion. You might be a family member in the future.


Why to Have the Future in Mind

If you are not looking forward to family meetings, you are not alone. Many people don’t. But keep in mind, it is just a day every so often. Make the best out of it. Always remember, the only family members you can chose are your spouse and your pets. The rest are free bees. These free bees can be scary, a mix or all awesome. Lucky you! Then you have all reasons to look forward to the next family reunion.

However, keep in mind, you never know who later will join the family. There might be that annoying person, who laughs about everyone, but themselves in the future. Thus, protect yourself by dressing timelessly at all family reunions. Or like the Godfather said

Keep your friends close, your enemies closer. - The Godfather #quote Click To Tweet


Consider the Reason for the Family Gathering

Sure, your daughter’s, step son’s, niece’s, nephew’s, sister’s, you name it, a church, beach or afternoon wedding, a Christening or name giving or other religious celebrations are also occasions where the relatives meet. However, such occasions have their very own dress code. But nevertheless, make sure you wear something timeless.


Outfit Idea for a Family Reunion

The OOTD in this post shows an example of a timeless American Classic look, i.e. my primary style. Recall the photos of Jackie Kennedy on the yacht of Aristotle Onassis? She wore a riding jacket, sweater, and pants. The pants are straight, which is always in style. To create the ageless look, I layered a fuchsia wool cashmere sweater over a brown slim, body-conscious layering top. The tailored cut of the blazer, and the sleek style of the sweater keep the look lean despite of three layers plus underwear. More on winter style layering in this guide.

Avoid any extremes with respect to your pants when dressing for a family meeting. #dress4success Click To Tweet

When you liked these Dress for Success tips tell your fiends about it by tweeting See these great tips on what to wear to a family meeting. #dress4success Click To Tweet


Wrapping Up What Is Best to Wear at a Family Reunion

In a nutshell, when dressing for a family reunion stay on the classic side and express your own style with just one (trendy) item. Don’t underestimate the hidden family reunions that often are not called like such. This can be dressing for Father’s Day, Mother’s Day, a Christening, graduation, or even dressing for a small civil wedding. It’s best to stay with the dress codes for these respective occasions. You can look stunning at commencement.

When you want more of such tips for other dressing situations and/or want to speed up to look your best ever, you may want to buy my book How to Dress for Success in Midlife. It’s a perfect gift too!

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Photos: G. Kramm

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