Fashion over 40: 4 tips to find clothes you love

Facebook groups are battlegrounds and ones for midlife women include raging debates around politics, parenting, relationships, and being in the sandwich generation with needy Boomer parents and rizz-obsessed progeny. But there’s one topic everyone in my nearly 10,000-person working moms group agrees on: A personal stylist named Ann Sugg. To the women in this group, she’s everything from a genius to a wizard to a superhero to a therapist. 

Sugg has had the styling bug since childhood, when she often helped family and friends get dressed for big events. As an adult, she worked in apparel sourcing and at a museum, then had a career shift in her mid 40s, when she began working as a personal stylist for a storied department store. When that happened, her girlfriends all noted that she found someone to pay her for what she’d done for them forever. 

As client Stephanie Goldman Thomas put it, “The older I’ve gotten, I’ve lost the drive and patience for clothes shopping…Ann takes away that anxiety because all I had to do was try things on; she had a roomful of items waiting. She takes all the ‘hunting’ out of the experience, which is the most difficult part.”

New ways to shop for your body and style:

Given all of the life changes in midlife (motherhood, divorce, change in body shape, changing careers), women can feel lost when it comes to adapting their personal style to who they’ve become. We talked to Sugg about how to get back your fashion mojo and find a personal style that reflects your current you. 

1. Embrace stores’ stylist and shopping services (they’re often free!) 

Sugg’s first insight is that many stores offer complimentary stylist and shopping services, which many women don’t know they can easily access, afford and benefit from. “Even giving yourself permission to touch and then try something on can be a barrier of entry for some women,” Sugg notes. “Having a neutral party pick something out lowers that barrier.”

Sugg believes it’s a trust fall every time — and her clients want honesty. “This is what I see…the shape of your waist. You have hips, yes, and this dress glides over them beautifully. Their brains don’t register what’s looking great. Mine does.”

There’s a magic moment when Sugg knows a look clicks. “The universal way I know we did well is a smile that everyone gets when they look in the mirror and feel good. It’s not a big cheesy grin, just a turn of the corner of the mouth. It’s a smile to themselves.” 

2. Question your own “rules” about your body 

“I still hear ‘I hate shopping’ all the time,” Sugg says. “Women come in with lists of problem areas and apologies for our bodies, coloring, and even our personalities. Once women are in midlife, their list of things they will not and believe they cannot wear solidifies. It also limits us.”

Sugg is sympathetic — our bodies do shift and change as we age, and many of us welcome what she’s dubbed the “menopause middle.” She’s also adamant that many of our cannots and will-nots can be challenged to our benefit. 

“You don’t know what something will look like, especially a dress, from the hanger.” Sugg suggests trying it on anyway. “The number of times I’ve heard, ‘I don’t wear things like this,’ and then, ‘Ohhhhh.’”

3. Embrace items that are modern and modular

In the past, external forces imposed fashion rules for the 40+ set. No-nos included short skirts or sleeveless shirts. Mercifully, Sugg no longer hears those tropes as frequently.

Today, her clients are dating again after a divorce, re-entering the workforce post-kids, moving up the career ladder, or negotiating a hybrid role that doesn’t require the same work/home wardrobe bifurcation. These milestones are wrought with stress and insecurities. 

Sugg sees opportunities to act and look our ages proudly. “I use the word modern because many in our 40s or 50s aren’t trying to look trendy. We want to stay current or look modern. We can be aware of what’s going on in fashion without feeling bound to it like we did in our 20s.”

“The thing about clothes during this time is that you need to know how to style [individual] pieces because we don’t really buy outfits anymore,” Sugg says.” “If you think modularly, you can take four items of clothing, change the shoes, add earrings and wear it almost anywhere.” 

Still, Sugg says most women would benefit from black pants and a pair of jeans we feel awesome in (dark wash denim dresses up easier). She says to invest in statement pieces that fit your body now, and then have fun (and spend less) on pretty blouses and layering basics. 

4. Adopt positive self-talk while shopping in 4 easy ways

According to Sugg, we can become geniuses at negative self-talk. Here’s how she helps clients open themselves up to the possibility they are drop-dead gorgeous:

1. Go into actual stores

“Shopping online is convenient, but few midlife and what are now termed “midsized” bodies are shown. Whenever you can, go try things on. And if you have to do it at home, invest in a full-length mirror!”

2. Embrace proportion

“When a woman says she doesn’t like her legs, hips or can’t show her arms — especially her arms! — I encourage her that if her body part is in proportion to her body, she’s just fine. No one else is seeing or focusing on whatever it is she sees.”

3. Say, “We can do better!”

“They aren’t all winners. If you, or a friend, tries something on and looks uncomfortable or is in something ill-fitting, practice saying, ‘We can do better.’ It makes it about a clothing choice and less about a body.”

4. Beyoncé your body

“You found a great dress, and you’re still feeling insecure. That’s ok! If you feel crepey or pale or whatever, take care of your skin. Put some self tanner on, put some oil on, lotion those legs up. You think Beyoncé isn’t doing that every single time she gets dressed?”