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Help me style my old wardrobe, please

old chic

Having retired last year, I don't want to spend a ton of money on new clothes, especially since my closets are absolutely stuffed. So I am trying to build outfits for my new, mostly casual and social life from the remains of my old, bifurcated executive work/Saturday ultra-casual wardrobe. Add in the problem that my weight has shifted to around the middle, whereas I used to have a relatively teeny waist. Therefore, most of my jackets no longer fit properly or flatter, but they have always been my mainstays. Structured black jackets are my favorite items of clothing still and the "antique" jackets are the highest quality pieces I own. I'd hate to part with some really unique Armanis and Gallianos.

Please ladies, give me some ideas for what I can do to make these things into fresh outfits! It might help that I can sew and could alter some things by shortening sleeve lengths, removing shoulder pads, etc. And you name an accessory and I have probably collected it over the years (except for BIG jewelry). I am also completely mad for shoes and have lots to choose from. I would love to have any suggestions you can dream up to make these old darlings useful again. I've always preferred unique items rather than the most currently trendy, but I do enjoy starting a trend in my circle.

For starters, here's what I wore to a relatively casual church service today. The lighting is pretty bad, so you can't really see, but the jacket is a black with white pinstripe wrap tied at a high waist. It was part of a business suit, but here I put it with black skinnies and some patent spectators that almost never come out of my closet. Should I have worn different bottoms? a tee? booties? heeled black/brown oxfords? Can this jacket be saved?

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Dressing

14 replies

Latest reply was from Mare

Gaylene

Veteran

Ah, yes--how to create a functional retirement wardrobe from a closet filled with boardroom-appropriate attire and Saturday-hang-around-house clothes. Transforming boardroom attire into smart casual is much harder in reality than it sounds in theory. Honestly, when the dust settled after a couple of years of retirement, I realized that I had banished almost all of my pre-retirement work wardrobe to the guest room because it just didn't work for my life anymore.

For what it's worth, here are some of my thoughts:

Pick out your favorite items from your corporate wear and put them at the front of your closet. Give them a cold hard look and judge if they would play nicely with casual clothes like jeans, skirts, and pants and, most importantly, if you'd be happy wearing those items running a quick errand to the store, making dinner, going for a walk--in short, what you will be doing 80-90% of your day--without wanting changing into "something more comfortable". It's fine to keep some items for "outside", but the reality is the bulk of your closet needs to be clothes you'd happily wear while you go about your normal errands and activities or you'll be in those ultra-casual, Saturday clothes 90% of the time.

It also takes some time to figure out YOUR version of a smart-casual, retirement wardrobe--and you'll save yourself time if you aren't too stubborn about what is your "look". (A lesson I resisted for quite some time, I'll admit!). Everyone is different--you might be comfortable cooking and cleaning in silk shirts and jewelry, or you might recoil at using your cashmere sweaters for gardening--but it helps to be realistic about what you will be doing during the day and what your comfort needs are for those activities. Your need for variety may also change once you aren't in the midst of a work environment.

In my case, after a few years of retirement, I realized my wardrobe contained very few pieces from my former business life. I've moved on, and, instead of spending my time and effort on trying to find ways to wear my former favorites, I prefer to spend my time on other activities.

old chic

Those sound like wise words, Gaylene. I have been resisting doing these sensible things for quite some time now. I am going to take the time and make the effort to think this through more and focus on the here and now. One thing I learned this past winter is that softer toppers are a lot more comfortable IRL. Maybe I will save a few special darlings from executive days, though.
And something else I'm looking for is ideas on how to deconstruct a whole load of v-neck cashmere sweaters that are too snug (meant to be worn under a suit jacket) for these days and, in some cases, have moth holes.

Gaylene

Veteran

Oh, yes, those cashmere sweaters...fond memories of my stash of polo, crew and V-necks that were my staples under an interesting, tailored jacket. My previous-life uniform.

Well, they were mostly turned into stuffed animals when I finally dropped the bulk of them off at a craft guild whose members were delighted to turn them into teddy bears and such for their annual fundraising event. A few pricey favorites hung around my closet for a bit, but, honestly weren't very hospitable to wearing with my less tailored items. Too "sweater girlish" on their own and I rarely wore indoor jackets anymore, so they languished at the back of my closet.

What did need to be upgraded, though, was my outerwear collection. In my working years, a coat was something I threw on over a jacket and removed once I arrived in my office. In retirement, my outerwear coats and jackets have became the "third piece" of my outfit so I devote more attention to finding just the right leather, trench, or utility jacket. My outerwear is what most people see me wearing these days so I've become much more willing to spend money on that part of my wardrobe.

ETA: Oh, I should add that a couple of my polo neck cashmere sweaters became an indispensable part of my ski capsule--and a couple of cardigans got used as loungewear. Felt decadent, but at least I was wearing them.

kkards

Veteran

Old Chic, I'm not retired, so please take what I say with a grain of salt. But I think if you really want to make a suit jacket casual, all the suporting pieces need to be casual. So, yes, I'd try a tee, and I'd probably try a really casual shoe, like a sneaker. And maybe try the cashmere sweaters over one of the high/low tanks that seem to be everywhere this year.

CocoLion

(website)

Veteran

I like your church outfit. I would keep any pieces (Armani etc.) that have value to you. The jacket pictured does not seem dated, it's got a timeless look.

As for the rest of your wardrobe, I would sit down with pen and paper and figure out what your activities are for the year. I did this a few times and it was really helpful. I counted the days I needed workwear (in my case, a uniform), then the number of days I needed very casual, at home wear -- by season. Then, I estimated the number of smart casual outfits I'd need. This would be for things like, dinner out, movies, going to San Francisco or LA (I live in rural California). Next, I looked at any special trips I had planned. In 2014 for example, I took a cruise to Hawaii with my Mom, and I needed dinner attire, swim wear, daytime pieces, plus a few formal outfits for that. The last thing I did was count the number of theater, opera and ballet dates I had. I know this a year in advance because I share subscriptions with family members.

This exercise, I'll call it a needs analysis, helped me not only to edit my closet, but also helped me be a more realistic shopper. My greatest weakness is over-shopping for the smart casual capsule when I don't have a need to add to it.

Sal

Veteran

Love the outfit shown above!! Very stylish.

Some good advice above, and it is so dependent on you and your lifestyle. My Mum is retired and she lives in jeans, merino sweaters, flat shoes and the odd warm topper when needed. My Aunt who is retired is never seen in jeans and wears jackets, blouses, skirts and even heels around in the house.

A couple of ideas for the cashmere:
Layering under gilets or soft jackets or even puffers. Or vests.
Lounge wear/active wear.
Donating to a family member or friend.
Making them into cushions.
Could any of them be converted into vests to wear over a shirt, or a cardigan that you wear undone?

Enjoy your retirement!!

rabbit

Veteran

Lot's of good advice. I echo what Cocolion and Gaylene say about figuring out your daily needs wear -- which you might not immediately have a sense of, depending what new activities you might take up.

I also echo what Kiwigal says about so much depending on your preferences/lifestyle. From what I've seen so far of your outfits I associate your style with polish, bold high contrast black and whites, and avant-garde/retro touches and tailoring so your casual wear might be closer to Caro's or Deborah from Oz for example.

I'm not retired, but if I only dressed for my daily needs (working from a messy home studio) there would be little point in having fun with fashion at all -- and I already did that for several decades. So I think there is a needs/wants/happiness balance, with practicality thrown in there. You might not want to wear a fragile top washing dishes or housecleaning, but really you can dress up a bit running to the grocery store if you want to --- I do because it makes it feel like an outing. (I like your church outfit, I doesn't read particularly casual, but it looks great).

In terms of your older clothes --- if they don't fit right or are damaged, that seems like a good idea to pass them on regardless (or consign the undamaged ones, I see a lot of cashmere at consignment in all sizes and shapes).

Carla

Veteran

Did a closet edit with DH and used a flow chart. It worked beautifully. Especially the advice that when evaluating something that looked like a "keep" you create 3 outfits that you could/would wear 'that week'.

I think we used the closet detox worksheet from 'Into Mind'.

Sherry

I believe it was Angie who once advised that what you decide to keep to wear should be worn frequently and with enthusiasm, or bless someone else with those pieces that no longer work in your life. If you can't use them, or they don't bring you joy upon wearing , pass them on to someone else who may need some good career staples. You have entered a different phase of life and while you transition into the new lifestyle and the clothes that you will enjoy wearing going forward, you might want to implement the excellent ideas other bloggers have posted above this one. But --cashmere with moth holes --that will never make you feel good in the wearing --donate it to some charity for it to be repurposed. Jackets or blazers that you just can't part with can be paired with tees and jeans, or create unmatched suits with an existing solid jacket or blazer and a coordinating patterned skirt or tweed trousers for dressier occasions. This will take some time for you to discover the types and amounts of clothes you will now need and prefer for this new lifestyle. As Fly lady says "baby steps ". You don't need to revamp your entire closet overnight. You didn't acquire all of those existing pieces over night, so give yourself time. If you need ideas on pulling multiple outfits together with minimal pieces, I recommend that you visit The Vivienne Files for basic ideas on color coordination as well as units or cores of wardrobe capsule pieces to create new outfits. You may already own many pieces that you may not have thought of pairing . Take your time and welcome to this new part of your life and -----congratulations !

Sherry

Oh, I forgot to mention that Janice Riggs, author of The Vivienne Files has also done some wonderful posts on how various clusters of accessories in several different given colors can really change the look of existing basic clothing outfits.

anne

Veteran

You are receiving some excellent advice so I won't add to it - just wanted to say that I love your outfit!

Suz

(website)

Veteran

You have received some terrific advice and I look forward to seeing where your style journey takes you.

Missey

Veteran

Hmmm...I'm going to need to see photos of your shoes, ALL OF THEM

Mare

I'm in a similar position, having retired from high finance in the North to 24/7 with dogs in the South. What I've done is still wear a lot of my favorites, if they get damaged so be it; converted most of my pants to dressier shorts and altered most of my dress shirts to short or sleeveless and in many cases removed the collar entirely to make them less weighty and less fussy.