How do you get dressed?

Before you get cute, I don’t mean the proverbial one pant leg at a time…

I mean, when and how do you decide what to wear? What goes into your decision?

I admit I usually think about what I’m going to wear the night before. I check the weather- temperature, rain, etc. Then I look at my schedule for the day. And then I think about something I read in a book recently-

If you ran into someone from your past, would you be embarrassed to be seen like this?

For example- yesterday I knew that I was going to spend my day writing, walking the dog, running errands, organizing the cabinets and getting my hair cut and colored. I went with black joggers, black tee and an oversized hoodie with sneakers. The joggers are somewhat tailored, and the hoodie was artfully oversized, so the outfit was comfy but neat. Of course, in the afternoon we reached temps in the low 70s, so I traded out the hoodie for a thin long cardigan. This outfit let me feel comfortable and confident and put together. I would not have felt weird if I’d run into someone from my past in this outfit.

This morning I had a 7am zoom call with my writing group. For this I wore my oversized fleece sweat pants and a black tee. I will walk the dog in this, but I would NOT want to be seen in this outfit by someone I hadn’t seen in years. While it’s easy to throw this on after a shower, it is not how I really want to present myself to the world. I plan to wear this outfit until about 12pm when I am going to change into a black midi dress and a white silk shacket. My only decision is footwear (knee high boots or loafers) I have book club this afternoon and then we are going to my sister in laws for Passover this evening. That is the outfit I want to present myself to the world in.

I know some of you are going to say that it doesn’t matter what you wear, or how someone views you. And those who say this have a valid point- what you wear doesn’t define who you are…

But make no mistake- it says something about you…

Should you care about what you wear?

Here’s my take:

One shouldn’t care about being on trend or fashionable. One shouldn’t care about logos or labels. Who cares if a bag is stamped LV or your shoes have red bottoms. Price point or fancy name shouldn’t matter. It shouldn’t matter if you get your clothes from a boutique or from a thrift store- price point and ambience shouldn’t matter…

I do think that some respect should be made as to the event you are going to, or what you are doing. This doesn’t mean to change you style- I wear black all year no matter where I am, which makes me stand out everyplace except NYC, and I don’t care. That’s my thing and I’m doing it.

However, I’m not wearing jeans and sneakers to a Saturday night wedding, unless the wedding is a hoe down in a barn and the happy couple are sporting overalls…

But if you are out and about in an outfit that you would be embarrassed to be seen in, why are you wearing it?

I’m going to walk my dog and go to the farmers market in this I picked it up off the floor outfit because it’s a convenient place holder for me accomplishing certain tasks. But this outfit, while comfy, does not make me feel like the polished, sophisticated woman that I pretend to be…

Does your clothing choice and daily outfit selection resemble the person you are/are trying to be?

Do you feel confident?

Do you feel like you could take on whatever gets thrown at you?

Do you feel like it doesn’t matter if anyone notices you?

Are you trying to hide from the world at large and be as inconspicuous as possible?

Why do you dress the way you do? (you don’t have to answer this question in public, but I would like you to think about your answer)

Look at what you’re wearing: would you want to run into someone you used to know wearing this outfit? Why or why not?

What does your clothing choice say about you?

88 thoughts on “Anything Can Happen Friday: How do you get dressed”

  2. I think the Pandemic did a number on the way people dress. After so many months of being house-bound, a lot of people just became comfortable wearing whatever they want and not worrying about it. The thing is, I feel better about myself when I’m somewhat put together, and I’m always relieved when I’m not the worst dressed person in the supermarket.

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  3. I’ll read the post in its entirety tonight or this weekend, but had to comment that it’s so exciting to wear a building t-shirt and jeans, cords or cargo pants on Fridays. AND, we had classes and no clients Monday so I was in company t-shirt and cords or Monday! What a great week! (I had two days of skirt breaks 🙂 ).

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  4. I don’t really think hard about it … what ever is at the top of my drawers when I open them I wear as long as the colors match. I like wearing shorts, tank tops, and flip flops. But of course at parties or formal ceremonies I wear what I am told to wear by my wife. 🙂

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  5. So honestly I literally laughed/sputtered when I read “how do you decide what to wear’! I wear the same thing almost everyday! Not literally, except perhaps for the jeans, but it is 99% jeans, a weather appropriate shirt and if needed a light jacket over that. In summer I replace the jeans with shorts. I have leggings- for exercise- don’t wear them out except to walk. I have nicer casual pants and a few shirts to go with- don’t wear them unless the need arises- like a more than casual dinner- which hasn’t happened in years. I have no dresses. The last dress I owned was probably for my sons wedding in 2013. We lead a very different lifestyle LA and I love you for asking this question this morning!

    Do I care what I wear- nope as long as I feel comfortable. My clothes are absolutely me. No one would recognize me in anything but my jeans so yes I feel confident to the max, happy, content in who I am, absolutely don’t need to be noticed by anyone, but should I run into an old acquaintance they would know me immediately. My clothes say: this woman will not be swayed by trends and only wears what she likes, mostly to just cover her body and nothing more! 😉

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  6. Love this post, LA. I fall into the camp of wanting to be comfortable, more and more, and the feeling of fabrics, textures matter so much…and I do spend a bit of time thinking about clothes, in relationship to weather, activities, footwear, which bag I’ll grab and load up for whatever adventure awaits. I’m grateful that I have a walk-in closet that’s **mostly** organized and I’ve done the ‘capsule wardrobe’ process a few times to thin the volume. I won’t lie. I like fashion, I like clothes! And your description of your black midi dress with a white silk jacket sounds lovely. 🥰

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    1. I am a big fan of capsule wardrobe. I recently read a book that talks about outfit formulas…which is figuring out the right silhouette and working with your wardrobe to see what works. It’s a cool concept

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  7. I have a different feeling about dressing. Please don’t take offense, and remember you should wear what YOU like and what you find comfortable. So it shouldn’t matter what anyone else likes.
    However, I personally don’t like the look of joggers. I wear them around the house all the time. I’ve had to wear them after several surgeries because of the adjustable waistband. But I normally wouldn’t wear them out of the house. I just don’t care for their look.. To me, they look like I’m in my pj’s. Plus, I think they look sloppy. And I bought several pairs and sets knowing I would need them after surgery. I have solid colors, camouflage colors, blue floral colored joggers. Yep, I have them in a variety of shades and have had to wear them for what seems like forever. I am still swollen after my last surgery plus cancer causes fluid in the abdomen so joggers do help with that issue.

    That being said, In spite of their usefulness and comfort level, they look like sweat pants to me. And even though mine are tailored, with a thin leg, ( some with cute prints and that have matching jackets or hoodies). They still look like gym pants. I didn’t mind when yoga pants were used for exercise because they looked like cute slacks . But joggers, in my opinion, look like tailored sweat pants. So, while I am not offended by anyone in joggers, it just says to me that that person is either going or coming from the gym or too lazy to get dressed so they throw on joggers. Again, just my opinion. But, I don’t think they flatter any woman of any age.

    I personally am a denim girl. Not regular denim, but premium denim with a touch of stretch for comfort , often embroidered or vintage wash. Bootcut, straight legged, skinny, I love them all. A great pair of jeans topped with a pretty blouse or three quarter sleeved tshirt, and a blazer is my favorite look. So, no to joggers, yes to jeans, boots, or sneakers, top, blazer is my go to. When my good friend from college visits from NYC she laughs because she tells me I look more NYC than she does. Because when she visits Fl she dresses for a warm climate and I pretty much dress the same all year round. Except during spring and summer I wear capri length jeans instead of ankle length.
    .

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  8. It’s a really interesting post, with some thought-provoking questions; but it’s also been really interesting to read everyone’s responses.

    Like Lesley, I don’t like joggers or loose fitting trousers generally. I don’t tend to think about how they look on others, I just don’t like the way they look on me.

    I would say that, for me, I don’t really think about what others think. I wear what makes me feel comfortable, but I think I had fallen into a trap of just throwing on anything and not giving it much thought beyond did it fit. Realising that, I’m now trying to get my weight down, and my fitness and energy levels up. I want to wear clothes that, yes, are still comfortable but that reflect who I am and the image I want to portray.

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    1. Everyone has their thing. I never wear jeans, and I rarely wear color other than an occasional pink piece…but we should feel good about ourselves when we leave the house

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  10. You made me laugh – thanks. I have gone through phases over the years having returned to my teenage years – not that I really left you see. Jeans, t-shirts, hoodies, cargo shorts and flip-flops almost all year round. I just don’t care what people think. That is the image I am trying to project – “who cares about fads or the latest trends or the trend setters for that matter.” Unless of course, I am making a significant purchase. We bought a new car last year and I dressed very nicely. I was able to get a deal with all kinds of free add ons that would probably not have happend if I was in a hoodie.

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    3. It’s funny, years and years and years ago, while on vacation, we stopped by the Ritz-Carlton in San Francisco. It was more than a decade ago, so don’t ask me why. What I do remember very clearly is that we were wearing our usual t-shirt and jeans vacation-wear, and all the attendants at the Ritz-Carlton were EXTREMELY courteous, not just a little bit, but EXTREMELY.

      We talked this over and figured that in the Silicon Valley area, the tech-rich might be much more likely to wear t-shirt and jeans, and maybe a hoodie, too, than a suit 🙂 So they didn’t want to risk offending a potentially uber-rich personage in t-shirt and jeans.

      I guess “location, location, location” holds even for clothes. I doubt in London we would have gotten the same treatment at their Ritz-Carlton in t-shirt and jeans? 🙂

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      1. Some stores/restaurants in nyc can be very uppity if you’re not dressed the way they think you should be…I try not to frequent places like that…

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  12. I’m all about comfort. Most of the time I’m in leggings and a top. I do think that there are certain places and times when particular attention should be paid to attire (the ones you mentioned). I don’t research the night before, preferring to just see what it looks like out when I’m ready to get dressed and I hardly ever change clothes in the middle of the day unless it is hot and I have to go to something short sleeved or if we are going out at night (or if I spill something on myself – LOL)

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  13. As a retired, non-working 70 year old male, my wardrobe usually consists of sweat pants and a tee. Later on, I switch to the Wranglers I’ve been wearing for about two weeks now. Of course, I think I’m gorgeous. But then, I don’t have to look at me.
    Have a Happy Easter.

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  14. I love this post because as you may remember I worked with clothing in NY and love shopping, clothing, etc. Garment Center. I often wear black in Florida and I have done so wherever I am. Just today as I was running about doing my chores, and watering in the garden, my pt exercises-I was at Lowe’s with the husband and finally noticed that black pants were very hot to wear today! While I in the library renewing my card I asked about my novel which will be published this summer the procedure for the library carrying my book. I was dressed simply in black exercise pants and a green cotton top-no make up but I felt confident. My husband had talked up my book to the librarian and shown her the cover. I felt great! Note: when I lived in NYC, it was so big that I relished the opportunity to get out and about in my free time walking dressed down. Of course, I was 27 and just a dab of lipstick and I looked great!! I do plan my outfits out if working or an important meeting. When I had a photo shot for the sleeve of my book the other day, I went all out with make up.

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  17. Comfort rules the day for me. I have a lot of stretch black pants (not tight leg) that work well with any shirt. I dress up a little for church and the occasional coffee date. I do pay attention to what the weather will be before it changes again. My main “rule” is “no pajamas with fluffy slippers at Walmart!”

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  18. 60 percent of the year… starched oxford cloth button-down…jeans or khakis, with London Fog type windbreaker…or v-neck…, maybe a hoodie… white classic reeboks… the other 40%….whatever keeps my frail ass warm.

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    2. Steve Jobs seemed to have a “uniform” of what to wear, mock black turtleneck and jeans, so he didn’t (his words) spend his energy on that instead of on creating the next i____ 🙂 Looks like you’re heading in his footsteps?

      It may work better for one of the most recognizable people this/last century than for the rest of us, though? 🙂

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      4. Well, I could vary or refresh my uniform a bit, if I were to stop purchasing all these Apple MacBooks, Mini’s, the Mac Studio, and sundry tablets. Liked your tidbit about the San Fan Ritz Carlton staff.

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  19. I almost never run into anyone from my past so makes no difference, I was also a lot thinner in High School & College, Wore my hair long and did’t wear glasses. So if anything I am unrecogizable. I wear whats comfortable/weather or funtion related. I wear image tees in the spring/summer some of which feature my own art. I dress more consertively in the fall/winter. I dress down as does management every day at work, if anything I never dress my age.

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  20. I laughed out loud at this sentence: “I check the weather- temperature, rain, etc. ” When I moved to Palm Springs from Seattle to live with my boyfriend (now husband of 37 years) I watched the weather every morning before I dressed for work. My hubby said, “Let me give you a hint. Warm and sunny.”

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  21. Ever see any of the Earnest movies? He had one look/ multiple pieces of the same clothes. that is me 95% of the time. Makes it easy to keep my wardrobe stocked. 😉 I am partial to nice t-shirts w/ a pocket… I had someone design a work t-shirt for me a few years ago. and incorporated several detail (type of fabric, color combo, etc. etc. My tastes are simple, and I know what I like. No need to dress like a slob. I do think how we dress does communicate to the rest of the world, things about us. (secure, insecure, in a funk, confident….

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    1. I am a big fan of the uniform. I almost always wear black dress or black pants /top, and then I add a cardigan or jacket and that’s how I change it up…but it’s the same basic uniform

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      1. just curious…did you do that in high school/ college/career season of your life, or a little later? (I’m asking because, I don’t think I really found my wardrobe groove, until I was in my 30’s,)

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      2. Late 30s. It’s when I realized that I was the only one who mattered when it came to clothes… (but I’ve been wearing mainly black clothes since my 20s)

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  22. I think that clothing like many things in life is quite paradoxical. If someone sees me out grocery shopping, I am likely wearing some kind of workout outfit, yet when I am at work, and out in the evening, it’s common for me to wear jeans/slacks and a blazer. I also have many tattoos, so that can add confusion too. I wear what’s comfortable, and appropriate for the occasion. How we dress actually matters in how we feel and perceive ourselves.

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  23. That’s an interesting question! I guess I would have to say that I dress for both comfort and confidence. I like to feel good about, and in, what I’m wearing. That’s not always the case, but it’s my goal!

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  24. There’s one particular item that I will always choose comfort over style with, and that’s shoes. At work we dress business casual. While there’s a lot of cute shoes and boots that would work well with my outfits, I stick to Skecher’s shoes, plain colors that match the color of my outfit. They’re not “pretty,” but I’m comfy.

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  25. I can’t fathom going out and about in whatever random stuff I happen to pick up…. I don’t even own sweatpants or leggings. Even if I’m just going to the grocery store or something like that on my day off, I put on jeans and pull my hair up. I don’t like feeling grungy when I go out, and I think people treat me better if I’m at least somewhat pulled together.

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    1. I’m like that mostly…like this morning I wanted to get to the bakery that gets a long line so I threw on sweats and raced down there…

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  26. As a guy with a wardrobe consisting of at least 50% thrift store chic, I’ve never been about labels (figurative or literal). I dress for comfort and success, never to impress. Then again, my office is very casual and I work from home three days a week anyway…

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  27. You just hit my Achilles heel. I don’t wear make-up, ever, or give my clothing much thought. I’m the worst. I know it. I own it. I do dress up for a special occasion but most days I’m writing/reading in leggings and a t-shirt. Ugg. I might need therapy. Hugs, C

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  28. I don’t give nearly as much thought to how I dress as I could. I don’t consider how I’d feel if I bumped in to someone from my past in terms of how I look, rather in terms of how I feel – either about myself or about them. My mother would be appalled with me – and often is – as she’s all about looking good and being seen to be so. I shed that particular skin a long time ago. Neat and tidy, not pulled through a hedge backwards, that’s it for me.

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  29. Your clothing choice does reflect your personality, whether you want it to or not.

    I think you should always choose something that is comfortable for you (and possibly) appropriate for the occasion. For example, my cousin wed in my grandmother’s backyard. I wasn’t sure what to wear because it’s a backyard in the middle of a rural city in Michigan. I wanted to show that I was at a wedding, but I also wanted to show that I was in a backyard. So, I went with a white t-shirt with LOVE across the front, black tu-tu looking skirt, and black heels.

    Did I stand out in photos, where folks were dressed as if we were in a church? Yep. Did I care. Nope.

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    1. I’m beginning to think there are those who think people don’t notice/judge you based on what you wear….they need a reality check. You can dress any way you like…own it…but your personality comes through

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