Fashion After 50 with Tim

Michelle (00:09)

Welcome to Decluttering 55 Plus with Michelle Passoff. This is the place to come for news you can use to get things done. Everybody knows that too much stuff is clutter and cleaning it makes you neater and tidier. To us, it is a life management tool that helps you navigate your next steps. This is what my book Lighten Up, Free Yourself from Clutter is all about. As Baby Boomers, we have a lot in front of us that is confounding and confronting.

So we sweep things under the carpet and put them off another day or forever. That is clutter because it keeps us stuck. And my new book addresses all of that. So we’re going to bring experts, authors, and authorities here to talk with us about health, relationships, technology, finance, housing. What are you going to do next in life, passing down your life stories, and even the challenges of making final arrangements. Here we aim to learn.

open new possibilities, choose, take action, and create a legacy, not a mess. So let’s get started. Since the age of 16, Tim Cregan has been working in the field of fashion. Today, he provides a unique service as a quote unquote wardrobe manager and owner of Together Creative. He edits wardrobes, reorganizes closets, is clothing and shopping consultant, and is a personal shopper for celebrities, executives.

by the hour workers, athletes, men and women, young and old. Regardless of budget, Tim works with people to use what they already own in stylish ways, choose a new silhouette that works for their body type, and in the end, create a wardrobe that fits different environments and occasions. When he’s not bringing his touch to a highly confidential list of clients, he has long been doing prop and fashion styling for magazines and corporate advertising clients. So welcome, Tim.

Tim (02:23)

Hey Michelle, thank you for having me here today.

Michelle (02:25)

Yeah, let’s talk about, want to talk today about redefining our wardrobes. A lot of people as they transition from a working life to a retirement life are kind of at a loss. And I think that ⁓ cleaning your closet is an opportunity to also clean your image up. So can you comment on how we can ⁓ clean our image change through our clothes?

Tim (02:55)

Sure, so many of us maybe have had years and years of sort of a corporate lifestyle where we were putting on the tie and putting on the jacket and heading off to work. And our wardrobe worked very well when we had a whole rack of jackets or stacks of white shirts. And maybe now we’ve changed. Maybe we’ve changed climates. Maybe we’ve retired or changed careers. And we’re not wearing those types of clothing. So it’s a prime time to really take a look at what do you own? What do you want to wear?

what are you wearing and maybe what isn’t working for your personal style.

Michelle (03:29)

What are you doing that you need to get dressed for? My father gave me some of my best fashion advice. said, dress appropriately. If you’re not going into a corporate office every day, if people still go into corporate offices, every day is not necessarily casual Friday when you’re working in a building or even when you’re working at home, you have to kind of look a certain way. I guess first you have to decide what you’re going to do with your time.

Tim (03:58)

So again, figuring out how’s what’s going on with me. I I’ve lived in many places in the country ⁓ before moving to Florida. This is my second time living in Florida. I was living in Minneapolis, Minnesota. And my wardrobe for Minneapolis looked very different than my wardrobe for Tampa, Florida.

Michelle (04:18)

Out with those down coats, huh?

Tim (04:20)

Exactly. And you know, maybe I didn’t need to keep, you know, I kept a few sweaters, but I certainly don’t need 30 sweaters. You know, there’s no need for it. But again, it kind of comes back to this. I touched real briefly on a term personal style. And a lot of times people think, oh, gosh, you know, I’m just not that person that wants to be wearing whatever the people, the magazines are telling us to wear. And that really, you know, that’s where personal style comes in. What is your personal style? What do you look?

and what do you feel best in? And that means you don’t have to really care much even for fashion, but it’s still, when we leave the house, we want to feel like we’re projecting ourselves in a way that, you know, we feel good. We feel good about ourselves. Who wants to walk out of the house not feeling good about themselves?

Michelle (05:06)

Yeah, but how do you how do you decide? Well, if you’re not, how do you know yourself? I guess that like, how do you should you are there people that can help you make that transition? Do a lot of the department stores have people that personal shoppers within the store hiring a personal shopper looking at magazines? How do you reinvent that image? How do you even know if you’re not necessarily like a fashion guru?

Tim (05:33)

Yeah, sure. I somebody like me, I I’ll come in, I’ll ask people, you know, sit down, hey, what are your favorite colors to wear? What colors do you look best in?

Even somebody I also kind of think about it in terms of people who aren’t into fashion You know because it’s very easy to talk fashion with people who are into fashion But I think what’s important is the majority of us, you know, we kind of pay attention a little bit But you know, we’re not delving into what’s new for the season So again for somebody I’m going to talk in terms of people who aren’t fashionistas Just start with what colors do you like to wear?

gosh, I hate to wear green or I love to wear blue. Okay, well that’s going to help us when we decide to either clear things out of our closet or maybe make a purchase in the future. When it comes to pants, you know, what pants look best on you? Do you look good ⁓ in a straight leg denim or are you going to look better in a looser pant or ⁓ pant lengths? You know, there’s all these kinds of things that we can sort of take a look at and we’re going to start from what do we feel the best at?

And that will really help you with your personal style. You can go to a department store and if you see somebody who has a style that you kind of like, maybe go up and talk to that person a little bit. Say, hey, you know what? I’m kind of maybe, maybe buying an item or two today, but I really like kind of your style. Tell me what inspires you when you get ready in the morning. So you don’t necessarily have to make it a big production and a big fashion overhauling. Or if you see a friend that you like their style, hey, tell me a little bit about what’s your style.

What kinds of things do you like to wear? ⁓ I like to wear, you know, I wear a lot of solid shirts, but then I like shirts that have a little bit of detail to them with a little bit of pattern. So I don’t do a ton of pattern in my personal, for my personal style, ⁓ but I do like to have little, little nods to something more unusual with everything that I wear.

Michelle (07:26)

So do you think, so the way I break down people when they retire is I think that there are people who continue working and they may work in a completely different profession. They may ⁓ volunteer, they may travel, which is something a lot of people do in ⁓ retirement. They may wanna just rest and relax. So do you have to think in terms of

activities and categories of clothing and assess your current wardrobe for whether it’s a match up for the activities that you’re doing.

Tim (08:03)

Certainly. Certainly, Michelle. have personally, I have a travel wardrobe. I have exactly what I wear that I take on every trip. I’ve got my key pants, shirts, jackets, things that don’t wrinkle, things that I could wash in a sink in a hotel room if need be and hang up for quick dry. So that’s for somebody who’s traveling. Somebody maybe who’s retired and now, you know, they have time to go out to

music events or go maybe more to dinners and things like that. You might want a few things that are a little, you know, have a little more fun and kick to them because you know what? You’re retired. This is kind of the fun time to, ⁓ sorry, there’s construction going on. Do you pick that up on the microphone? But maybe you ⁓ want to have some more clothes to kind of wear when you go out. You know, maybe it is that guy who’s always worn a white shirt.

Michelle (08:45)

That’s okay.

Tim (08:55)

And now he and his wife are going out and listening to live music and taking in sunsets and having a cocktail in the evening. Well, know what? Throw in a fun shirt or two to add with that new style of life that you’re leading.

Michelle (09:08)

So as you transition, you get to go shopping, actually. can go shopping first in your closet, right? And what would you pick out of your closet?

Tim (09:17)

Sure, first step is when you go into your closet, you’re gonna want to take a look at what do you have, what’s working, what’s not working. As we mentioned just a little bit ago, if you ⁓ have that green shirt that you think, I don’t like how I look in green, well then why are you keeping green? If you’re like, I love how I look in blue, then you know what? Gravitate towards the colors that look and make you feel good.

Start with what you own. Try on your jeans, all your jeans. Take a look at them. Do I look good in these jeans or am I thinking, ⁓ these are the jeans that I’m gonna wear when I wake up on a Sunday and I’m just staying home or I’m gonna work in the garden? People will wanna keep multiple pairs of things like that. I always encourage them, how often are you really just waking up, getting dressed in something that you’d want nobody to see you in? Or if you’re not a gardener, ⁓ how many pairs of gardening pants do you truly need?

Michelle (10:13)

So about the days you’re gonna paint, you’re gonna pay.

Tim (10:15)

Okay, keep one pair of painter’s pants. I had that with a client who called and had everything painted in her house, but she wanted to keep, you know, four pairs of painter’s pants. like, I don’t think we need four pairs of painter pants. Keep one. And when you realize maybe you’re not wearing them in a year or so, you’ll get rid of those too.

Michelle (10:33)

So the first thing is clean out all the clothes from the past profession or past activities. You your mom jeans, your kids are all grown now, okay? ⁓ Time to re-up that attitude, re-up that closet, re-up that shopping experience. Do you go shopping in the same places as you might’ve gone shopping before? Do you have to change where you go to new stores that you might not have thought of?

Tim (11:00)

And things may change. mean, maybe when you were working full time and you had that regular paycheck coming in, you were happy to be going off to the big box department stores. And now as we’re sitting here talking and we’re saying, new fashion. And you’re like, wait a second. I’m now, I don’t see that paycheck coming in as regularly as it used to. ⁓ Remember, there’s great secondhand stores. ⁓ And take some time. Go flip through there because

I have found some absolute gems in those stores. And if you’re something like, but somebody wore it, well, whatever, wash it, send it to the dry cleaner. ⁓ A shirt bought at a secondhand store that even goes to the dry cleaner for $3 is still going to be a lot less expensive than maybe going to one of your big box department stores or exclusive boutiques.

Michelle (11:45)

Yeah, I didn’t think of that. That you may have a different budget when you’re not working than when you were working. So that’s a good idea, Tim. What else should we know about projecting yourself and how you feel in your clothes probably makes a difference. How you project yourself is going to be different in your business life as in your ⁓ retirement life. How do you…

How do you change the attitude?

Tim (12:17)

Yeah. again, remember every change in life, whether it’s getting a new job, maybe it’s the unexpected, you lost that job, but you’re still looking for something new. Maybe it’s a changing climate where you live. Just take a look at any of those as being a new opportunity to always again, kind of call it that, you know, put your best foot forward and what, you know, what are you going to feel? What are you going to feel good in? What are you going to, when you look in the mirror, think, you know what? I look good today.

Those are the kinds of things that we want to gravitate toward. if you don’t, if you really, mean, everybody has an opinion whether they’re wanting to admit it or not. I’ve worked with, typically it’s more guys are like, oh, I don’t care. just give me whatever to put on. You know what? But when all of a sudden they put on a shirt, they feel like, oh, you know, or even kind of using this one as an example, it’s a solid shirt with a little bit of detail. And you go out for dinner and somebody says, oh, you know, hey, George, you know, nice shirt there. You know, I like that little,

You know what, even if you don’t like fashion, everybody always likes a little pat on the back, you know, every now and again. So.

Michelle (13:23)

Yeah, for some people like fashion isn’t cool rather than fashion is cool. actually retirement might be a time to make fashion cool because ⁓ you have the time to really express yourself more than when you were working.

Tim (13:41)

And try things out, try something a little different. And if you really are questioning, because it can be daunting. I’m not trying to say it in a flippant way like, gosh, go try new things and make it happen today. Ask a trusted friend, take your spouse maybe, or somebody, maybe you don’t want the opinion of your spouse, but you want the opinion of someone. Whoever that person is that’s gonna give you some advice that you can rely on.

Michelle (14:02)

Stay!

It’s

gonna really fun. This is gonna be really fun to go out on that shopping excursion and say, completely reinvent yourself. What do you think about, as we’re talking, I’m just thinking about going and getting some magazines and tearing out the looks that you might want to have and matching up what you see in the magazines with what you buy.

Tim (14:32)

Sure, a few different things. Yes, take a look at magazines. could be, you know, it doesn’t even have to be with seeing how like ⁓ people in golf are dressing now. You could be looking at golf magazines and get fashion inspiration. You also may want to go, let’s say you’re going to go to a large retailer to really try things on and figure out what’s the new thing. And maybe even know that you’re kind of an impulsive person. Maybe leave your wallet at home and actually just go try things on.

Look at things in the fitting room. Take a picture of what maybe you like the look of yourself in. Maybe take a picture of stuff that you don’t like how you look in it. And that will also be a guide to help you educate yourself on what do you ultimately want to buy. I always just tell people, if you’re going, because I have sent clients just to go, I go, you know what? You’re going to go to the store. You’re going to try on 25 pairs of jeans and let’s figure out what you like and what you don’t like.

I always tell people make sure you re-hang it up on the hanger or refold that item so it’s easier for the person, the sales associate to put it back on the shelf.

Michelle (15:39)

You you remind me of ⁓ something that when you’re not going into the same office every day where people see you over and over and over, maybe you don’t need to buy as much when you transition from working to retirement. people aren’t, the same people every day aren’t gonna even be seeing you. should you, what’s your experience with tempering the volume of what you buy?

Tim (16:05)

It really is going to vary from person to person. ⁓ I work with people that have very large wardrobes that really want to be wearing different things all the time. Then there’s people like me. mean, this particular sweater jacket I have on right now. I have one sweater jacket. This is it. And you know what? If we’ve had dinner three times, you’ve probably seen me in it twice. And I really, think long gone are the days there used to be that whole thing like, don’t let them see where something twice, you know, you know,

It was mostly, I think, around like event dressing. You you wear a gorgeous dress to a wedding and you’re like, shoot, I’ve already worn that. Well, if you love it, why not wear it again? You know, and I think that goes pretty much true for any kind of clothing. You don’t have to have a huge wardrobe if you don’t want a huge wardrobe. My wardrobe is actually pretty small. I like to have quality items in my wardrobe that work for me. And if it doesn’t work for me, I get rid of it. And I would be much happier wearing

one sweater three days a week than wearing three sweaters on three different days.

Michelle (17:09)

Yeah. Yeah. So, um, you get to be your own boss in your retirement. You get to choose the colors you want. You get to choose the outfits you want to buy. You get to choose the volume, but, uh, cleaning the closet, bring in out, take out the olds, bring in the new reshape your image with your clothes. So I appreciate you. Go ahead. Tim, you’re going to say.

Tim (17:31)

We do also want to remember age appropriate. ⁓ I’m 57 years old and there’s certain things that I see in fashion because I’ve always really enjoyed fashion that I absolutely love. I saw a pair of sneakers last week that I was like, my gosh, these are amazing. I love them. But then I’m like, you know what, I’m 57 years old. ⁓ I say, don’t let your age be your cage. But you also have to kind of keep a little bit of what’s appropriate for

those of us that kind of this part of our lives versus when you’re 20. In this particular case, I just sent the picture to my son who’s 23 of the shoes. I said, do you like these? He’s like, oh yeah, they’re great. said, super. So I bought them and mailed them to him. So I’ll never wear them, but you know, maybe.

Michelle (18:14)

You’re buying appetite satisfied.

Tim (18:19)

And when people say, you know, kind of dress for your age and stuff, it doesn’t mean you have to be a stodgy dresser. It doesn’t mean you have to be a boring dresser or, you know, hyper conservative. ⁓ But there are just,

Michelle (18:32)

you might wear when you’re 20, you still might be in good shape, but you may not want, you know, that string bikini when you’re- Sure.

Tim (18:39)

You may have a gorgeous, gorgeous body at 60 years old, but you know what? Maybe a beautiful, sleek one piece is going to look every bit of good looking and sexy, if that’s kind what you’re trying to portray, as maybe that bikini that should be left back to somebody who’s in their 20s.

Michelle (19:01)

So, ⁓ yeah, age appropriateness. I think there’s merit in that. Like I said, you don’t have to be stodgy, but you can be appropriate. Wonderful. So everybody get out there cleaning your closet, get out there going shopping, ⁓ recreating your image for your next chapter of your life and the activities in which you’re being engaged. So…

I want to thank you, Tim, for coming today and giving us some ways in which we can refashion ourselves. ⁓ As you know, out there, I’m the author of Lighten Up, Free Yourself from Clutter. And I’ve long been clutter consulting, traveling back and forth across the country and around the world, telling people to let go of what they don’t want, need, and use, and love, and make it work for what’s next and what’s possible in your life. If you’re out there and your closets need you to hit the refresh button,

Let me be the first to say the time to start is now. Action is the only thing that makes a difference. So I want to thank Tim for helping to enlighten us about the virtues of cleaning our closets and inspiring us ⁓ to get busy refashioning ourselves for the next chapter. Just do it. Thank you.

Tim (20:18)

Thanks much Michelle for having me and I hope your listeners have a good time re-looking at their fashion and their personal style. Goodbye.

Michelle (20:27)

Well, that’s all we have time for today. So let’s wrap things up with a request that you’ve got to our website, www.decluttering55plus.com and click on the let’s connect button. Share your thoughts, insights and tell us the lessons you’ve learned. If you’re facing challenges or celebrating triumphs on your decluttering journey, we wanna hear from you. Connect with us on social media.

Like us on Facebook, follow us on Instagram, and subscribe to us on YouTube. Let us know you’re part of our community by rating and reviewing us from wherever you’re listening from today. And don’t forget, invite your friends and family, young and old, to tune in too. Let’s include them in the conversation. The more, the merrier. Thanks for being with us today. And until next time, this is Decluttering 55 Plus with Michelle Bassoff, wishing you a clutter-free day.