# Clothing anxiety



## joannacroc (Dec 17, 2014)

I'm normally not a terribly anxious person but am finally considering dating again after breaking up with LT BF over a year ago. A guy in a social group I belong to asked me on a date. I wasn't able to make it that time but we're maybe gonna go out in a few weeks when I return from a trip. I feel like I'm finally sort of ready to dip my toe into dating and attempting to do so minus OLD because it's not really a format that I like.

So I haven't dated dated in a few years and have zero idea about what is appropriate date...wear. I assume not work clothes, probably not athletic wear. I am 40 and want to look nice but not overdressed and not like I'm headed to a PTA meeting. What does one wear on a casual date? Help a sartorially challenged lady out? What is even appropriate anymore. I have no idea where to start and the what to wear anxiety is making me feel like a dumb teenager lol


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## ccpowerslave (Nov 21, 2020)

Joanna I have no idea but since you’re interested in running I’m going to guess you look great and the guy asked you because he likes you! You’ll be fine.


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## heartsbeating (May 2, 2011)

I'm offering this post in the hopes that it helps you to relax. I'd suggest to dress according to the activity of the date. I like to look 'good' yet that's subjective. What I personally like to wear may not be the next person's cup of tea, however, I'm good with that. I know what I feel good wearing and for the most part, what is flattering on me. And so I write that to suggest leading from that place for yourself. If he doesn't dig your style, eh so be it. Plus dressing for the activity... when my man and I have been to small music gigs, for example, and it's predictable that I'll be standing for hours at said gig, I'd likely wear some heeled boots that are comfy enough for that or potentially wear vans or similar. If we're on some kind of walking tour, I'm absolutely wearing comfy shoes. And the outfit then flows from there and based on weather and such. Similarly, a meal out, my usual attire on from demin are flowing dresses with boots. However, again depends on the venue and weather and such. That's just me though. I've gotten to the end of the paragraph and reflected that even in single night-club days, I'd be the one wearing my own style and not typical to what my peers were wearing. Therefore, I may be the last person you ought to be listening to. Anyway, I'd suggest what you feel good in, what is flattering, and what is practical to what you are doing. Wear the 'good' undergarments though. And choice perfume (if you're into that). Good luck!


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## TXTrini (Oct 2, 2013)

joannacroc said:


> I'm normally not a terribly anxious person but am finally considering dating again after breaking up with LT BF over a year ago. A guy in a social group I belong to asked me on a date. I wasn't able to make it that time but we're maybe gonna go out in a few weeks when I return from a trip. I feel like I'm finally sort of ready to dip my toe into dating and attempting to do so minus OLD because it's not really a format that I like.
> 
> So I haven't dated dated in a few years and have zero idea about what is appropriate date...wear. I assume not work clothes, probably not athletic wear. I am 40 and want to look nice but not overdressed and not like I'm headed to a PTA meeting. What does one wear on a casual date? Help a sartorially challenged lady out? What is even appropriate anymore. I have no idea where to start and the what to wear anxiety is making me feel like a dumb teenager lol


Are you a jeans girl or a dress girl?

I personally like dresses, they're comfy and easy. Yesterday for casual but comfy date night, I wore a colorful sleeveless v-neck peplum top (fit and flare) and black silk shorts and wedge sandals. Otherwise short sundresses, mini skirts and tops. I always do my hair and makeup too since I don't when we stay in.

At 42, I don't dress trendy or like I'm trying to look younger. Nothing super low-cut, too short or too tight. I pay attention to fit and materials- no polyester or anything too cheap looking. The devil is in the details, I leave the trendy junkie stuff and pajamas to go out to 20 somethings.


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## DownByTheRiver (Jul 2, 2020)

If you're going someplace casual, wear jeans or pants but wear a feminine top, something blousy and a v-neck. 

If you're going somewhere dressier, a dress or just add a skirt to the above. 

When I was in my late 40s my new uniform was ruffled v-neck blouse worn with sheer lined layered chiffon straight or A-line skirts that were real light and comfortable. Sometimes boots are more comfortable than feminine shoes. Don't know where you would find those anymore though because I haven't been able to go shopping in stores in quite a while.


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## heartsbeating (May 2, 2011)

TXTrini said:


> Are you a jeans girl or a dress girl?
> 
> I personally like dresses, they're comfy and easy. Yesterday for casual but comfy date night, I wore a colorful sleeveless v-neck peplum top (fit and flare) and black silk shorts and wedge sandals. Otherwise short sundresses, mini skirts and tops. I always do my hair and makeup too since I don't when we stay in.
> 
> At 42, I don't dress trendy or like I'm trying to look younger. Nothing super low-cut, too short or too tight. I pay attention to fit and materials- no polyester or anything too cheap looking. The devil is in the details, I leave the trendy junkie stuff and pajamas to go out to 20 somethings.


Yes to fit and materials and detail.

When I converted to my latest look which I've stuck with for a few years now, it was quite different to the clothing choices I'd been making. The longer flowing dresses, that is. I'm in my 40s. A friend suggested that if I was wearing longer dresses, to balance it out with having a v-neck cut to accentuate my decolletage/cleavage so that I wouldn't look too covered up, and is also flattering. I think with clothing, it's like makeup (and which I wear). In that, if I'm wearing a brighter / bold lipstick then the eye makeup gets toned down. If I'm wearing more intense eye makeup, then the lipstick gets toned down. The dresses I like are, as I say, longer, yet they are fitted at the top and do have slight cleavage element going on, and fitted to the waist before flowing out. It's a style that suits me and I like to pair with a cropped cardigan or jacket, heeled boots just below the knee or ankle boots. As for material, recently out to dinner with my man and I wanted to wear jeans, however, I opted for black demin as I feel it looks slightly less casual, ankle boots that had a higher heel than my usual ones (yet didn't need to walk far), and while the top had me fully covered, it was satiny/silky type material on the front and sat just above my hip; that is to say, that my posture with the heels and length of the top flattered another asset. I had in mind a certain pair of earrings that matched well, yet as soon as I put them on I knew they were going to feel like a pain in the behind after a short while, so opted for a different pair. I felt good. Go for feeling good. Also while it may sound like a lot of thought was put into it, there really wasn't. Only upon writing this does it become more conscious. He responded positively to my clothing choice. Essentially it was jeans and a top. Yet as @TXTrini wisely stated, the devil is in the details. I also try to pay attention to shades and tones that are flattering to me.

I couldn't help but jump back in. It's a fun topic. This is a fun time for you!


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## RandomDude (Dec 18, 2010)

It depends on where you are going, what are the plans? If it's a dinner at a classy restaurant dress the part, if it's rock climbing wear comfy and light/no make up.


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## D0nnivain (Mar 13, 2021)

Make sure whatever you wear fits so you are not fussing with it. An outfit that makes you feel good about how you look will also boost your confidence. 

Jeans vs pants vs skirt vs dress all depends on where you are going & your personal style. 

Have fun!


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## ShatteredKat (Mar 23, 2016)

Asked a girlfriend for a date to go horseback riding. She said OK. Figured out she should wear long pants. Summer so top not to heavy type material. One thing she didn't think of - (maybe never been on a horse) is the ride can get bouncy.
She didn't wear a "sports bra." Unpleasant experience and ditto for taking girlfriend on a motorboat ride. They can get bouncy also. 

If you know where you plan to go - consider the inside or outside temperature. I wear a long sleeve shirt grocery shopping as the store keeps the temperature uncomfortably low for me. Movie? Sitting still for a couple hours in light clothing can get a bit cool. Drive in movie in Augusta, GA? thin clothes and a can of mosquito spray!

Don't wear makeup that can't get wet or if it does, runs down your face with the water dripping off. Girlfriend at pool party -

Dancing? Ask where and layer so you can shed some cloth when the exercise gets going.


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## Diana7 (Apr 19, 2016)

I don't really have a certain preference for fashion. If I like something I wear it but for first dates go smart casual. 
Maybe smart jeans or trousers(pants) with a nice blouse or other pretty top. 
Oh and I wish you all the best


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## Zedd (Jul 27, 2021)

Echoing others, it all depends on what activity you're doing, to start with. That said, it's most important that it's something that you're comfortable with and feel good in, and also, a pair of shoes/boots can completely change the look with everything else the same. My wife can wear jeans and a light sweater or something simple and it looks completely different and with an entirely different attitude if she's wearing her Chuck Taylors vs. a pair of strappy heels or boots.


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## Ragnar Ragnasson (Mar 4, 2018)

I'm no help. I went straight to hot and sexy but that's out of context.
Now I'm distracted and am trying to re-center. 🤣🤣🤣


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## joannacroc (Dec 17, 2014)

Ragnar Ragnasson said:


> I'm no help. I went straight to hot and sexy but that's out of context.
> Now I'm distracted and am trying to re-center. 🤣🤣🤣


Oh. OK. Do they make hot and sexy in size nerd? Pretty sure I own nothing that could be described as such. Usually just go with clothes that fit and mean that I am fully dressed before leaving the house, hence the problem.


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## Zedd (Jul 27, 2021)

Embracing your nerdery can be sexy. It's about how you own your nerdery.


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## Ragnar Ragnasson (Mar 4, 2018)

joannacroc said:


> Oh. OK. Do they make hot and sexy in size nerd? Pretty sure I own nothing that could be described as such. Usually just go with clothes that fit and mean that I am fully dressed before leaving the house, hence the problem.


You can find the magic balance 🙂🙂. Good to hear you're getting out and about!


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## joannacroc (Dec 17, 2014)

TXTrini said:


> Are you a jeans girl or a dress girl?
> 
> I personally like dresses, they're comfy and easy. Yesterday for casual but comfy date night, I wore a colorful sleeveless v-neck peplum top (fit and flare) and black silk shorts and wedge sandals. Otherwise short sundresses, mini skirts and tops. I always do my hair and makeup too since I don't when we stay in.
> 
> At 42, I don't dress trendy or like I'm trying to look younger. Nothing super low-cut, too short or too tight. I pay attention to fit and materials- no polyester or anything too cheap looking. The devil is in the details, I leave the trendy junkie stuff and pajamas to go out to 20 somethings.


I like fitted jeans and loose V neck T shirts for normal weekend days, with usually DM sandals or sneakers. I wear a dress if i'm going somewhere fancy. I own heels but walk like a constipated girafe in them so don't tend to wear them as much anymore. Wedge sandals, shorts and nice top are a good idea. Thanks. That sounds not too far of something I would feasibly wear.


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## TXTrini (Oct 2, 2013)

joannacroc said:


> I like fitted jeans and loose V neck T shirts for normal weekend days, with usually DM sandals or sneakers. I wear a dress if i'm going somewhere fancy. I own heels but walk like a constipated girafe in them so don't tend to wear them as much anymore. Wedge sandals, shorts and nice top are a good idea. Thanks. That sounds not too far of something I would feasibly wear.


Comfort is key! If you're miserable, it's hard to relax and enjoy yourself. It's been miserable in Texas, whats the weather like where you're at?

I hate heels too! I already have to take 2 steps to keep up with every step taller folks take, so glomping around in heels is no bueno... They've got really cute comfy wedge sandals these days, and don't forget to do your toes for a little boost!

Do you know what you guys are going to be doing? One guy sprung golfing on me after I showed up in tight jeans and a top and kept gawking at my butt when it was my turn. That made for an awkward time.


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## Diana7 (Apr 19, 2016)

Balance is the key here. Not too showy offie but not too plain.


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## Ragnar Ragnasson (Mar 4, 2018)

TXTrini said:


> Comfort is key! If you're miserable, it's hard to relax and enjoy yourself. It's been miserable in Texas, whats the weather like where you're at?
> 
> I hate heels too! I already have to take 2 steps to keep up with every step taller folks take, so glomping around in heels is no bueno... They've got really cute comfy wedge sandals these days, and don't forget to do your toes for a little boost!
> 
> Do you know what you guys are going to be doing? One guy sprung golfing on me after I showed up in tight jeans and a top and kept gawking at my butt when it was my turn. That made for an awkward time.


Maybe that indeed was his plan!


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## RebuildingMe (Aug 18, 2019)

I like casual summer dresses and open toed sandals. Just make sure you get a pedicure and clean up the feet.


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## TXTrini (Oct 2, 2013)

Diana7 said:


> Balance is the key here. Not too showy offie but not too plain.


That's entirely up to her.

Some people dress so far down, "showy offie" could be anything better than pajamas.


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## TexasMom1216 (Nov 3, 2021)

Business casual with fun jewelry?


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## LATERILUS79 (Apr 1, 2021)

Looks like you got a lot of great detailed advice from the women here. 

As a man, I'm with the rest of the guys here. You'll be fine.

Any suggestion I would make are broad strokes. Wear something comfortable and feminine. That's it. I think a lot of guys think like I do. It is rather pleasant to see a woman dress in feminine clothes. That doesn't mean "showy" types of clothing. I have no idea what the correct words are for the different types of clothing, but I assume you understand what I'm saying. There are clothes that are obviously made (and cut) for men and the same for women. 

He already likes you, hence the reason he asked you out on a date. I think he will be more than thrilled to see you dressed in comfortable clothing (for the activity you've all chosen) that is feminine. No need to show any skin, just feminine.


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## Diana7 (Apr 19, 2016)

TXTrini said:


> That's entirely up to her.
> 
> Some people dress so far down, "showy offie" could be anything better than pajamas.


Its all up to her, but she is asking for advise. People know that showie offie isnt pyjamas.


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## TXTrini (Oct 2, 2013)

Diana7 said:


> Its all up to her, but she is asking for advise. People know that showie offie isnt pyjamas.


Not the people wearing them...

Anyway, I'm offering advice as a fellow 40-something-year-old dating today.


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## Diana7 (Apr 19, 2016)

TXTrini said:


> Not the people wearing them...
> 
> Anyway, I'm offering advice as a fellow 40-something-year-old dating today.


As I was. In my 40's when I started dating again after a long time. 

Everyone has offered different advise. She can take what she wants and leave the rest.


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## Ragnar Ragnasson (Mar 4, 2018)

LATERILUS79 said:


> Looks like you got a lot of great detailed advice from the women here.
> 
> As a man, I'm with the rest of the guys here. You'll be fine.
> 
> ...


I recommend a little skin though.

But I'm a guy so there's that


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## Diana7 (Apr 19, 2016)

Ragnar Ragnasson said:


> I recommend a little skin though.
> 
> But I'm a guy so there's that


That's why I recommended that she took a balanced outlook in what she wore because some men would like a bit of skin and some may prefer a little more modesty. It does depend on the guy involved. In the end though she needs to just be herself and wear the sort of thing she usually does for an evening out. Something she feels comfortable but confident in.


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## joannacroc (Dec 17, 2014)

Update: first date this week (he is persistent) and apparently for sort of upscale casual drinks slash food. Getting a pedicure this week for the first time in like 3 years. Maybe it can counteract my runners feet?


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## TXTrini (Oct 2, 2013)

joannacroc said:


> Update: first date this week (he is persistent) and apparently for sort of upscale casual drinks slash food. Getting a pedicure this week for the first time in like 3 years. Maybe it can counteract my runners feet?


Hey, it can't hurt. In fact, it'll feel like heaven if they include a foot massage. 

So are you guys meeting up after work?


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## Zedd (Jul 27, 2021)

joannacroc said:


> Update: first date this week (he is persistent) and apparently for sort of upscale casual drinks slash food. Getting a pedicure this week for the first time in like 3 years. Maybe it can counteract my runners feet?


Well, to this guy's eyes, this sorta screams out flirty but conservative sundress and wedge sandals, if ya got 'em.


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## Diana7 (Apr 19, 2016)

joannacroc said:


> Update: first date this week (he is persistent) and apparently for sort of upscale casual drinks slash food. Getting a pedicure this week for the first time in like 3 years. Maybe it can counteract my runners feet?


Hope it goes well for you.


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## pastasauce79 (Mar 21, 2018)

I'm 42, and even though I'm married, I go out on dates with my husband. I like to wear fitted jeans (even during summer) with a nice top and sandals or flats. I wear dresses with sandals. I don't wear shorts to dates. I feel they are less dressy for a dinner date. 

I have to feel comfortable with whatever I'm wearing. My husband doesn't care what I wear, and I think most men don't care as long as you are not wearing pajamas and bunny slippers.

Have fun and enjoy your date!!


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## davjo (6 mo ago)

I understand your feelings. I visit my local therapist in Sydney, he helps me a lot.


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## Ragnar Ragnasson (Mar 4, 2018)

pastasauce79 said:


> I'm 42, and even though I'm married, I go out on dates with my husband. I like to wear fitted jeans (even during summer) with a nice top and sandals or flats. I wear dresses with sandals. I don't wear shorts to dates. I feel they are less dressy for a dinner date.
> 
> I have to feel comfortable with whatever I'm wearing. My husband doesn't care what I wear, and I think most men don't care as long as you are not wearing pajamas and bunny slippers.
> 
> Have fun and enjoy your date!!


Hey, don't knock the pajamas and bunny slippers! That would work too.


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