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City break with new boyfriend after divorce - help!

98 replies

lifeafterdivorce · 17/08/2025 06:43

I’ve just booked a city break in late September with a new partner. we’ve been seeing each other since January, but it’s the first relationship I’ve had after divorce, and the first new relationship for 20 years!! It’s been going very well but a holiday together feels like a big landmark and I’d like to look nice (and more importantly, feel good).

I’m 45, size 12, pear shaped, long back and short legs. I’m looking for one or two dresses that I feel great in, and one or two lovely tops that would work with wide leg trousers. Budget is flexible but ideally under £200 total. My usual shops are Cos, Uniqlo, Sweaty Betty

Boat neck and v neck shapes suit me, and green and blues are by far my most flattering colours. I usually wear navy as a neutral (though oddly after a lifetime of avoiding black as it drains me, I’ve recently started wearing it - would definitely consider a black dress or tops for evening). I like fabrics that feel good - soft or silky, fluffy wools, nice textures. Dresses need to drape or have some structure - nothing that clings, no lightweight jersey. It all needs to be fairly casual - footwear will be trainers or leather sandals.

its a city break in Europe and temperatures could be anything from 15-25 so nothing too lightweight. There will be lots of walking but also nice meals out. Also lots of time in the hotel room but I’m not worried about that bit - it’s dressing for outside where I need help!

I want to look relaxed but stylish, casually well dressed but not too middle aged. And not too glamorous as has to be consistent with my personality and normal life (dog walking, gardening, trousers and Birkenstocks rather than satin maxis and heels). Thinking Jo Whiley or Zoe Ball!

(also, I’d prefer to buy new I think - I do use Vinted but have had more failures than successes. I’d love specific item recommendations rather than categories (‘silk shirt’) if possible. Even better if it’s something you’ve tried - eg a dress that you’ve bought that you feel fabulous in. I’ve got a hankering for a lovely knit dress in soft wool but it needs to be very flattering on the tummy area!

sorry it’s a very broad question but would love some help!!

OP posts:
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Othersnotsomuch · 17/08/2025 06:44

Budget ?
where do you usually shop?

Othersnotsomuch · 17/08/2025 06:45

How many nights?

lifeafterdivorce · 17/08/2025 06:55

Budget, I’d usually pay up to £125 for a dress and ideally £50 for a top. Could go higher (have been considering a sezane chlo shirt at £100 for example). Can spend about £250 in total.

Shops - Cos, Uniqlo, i have a few shirts from WNU.

5 nights.

thank you!!!

OP posts:
lifeafterdivorce · 17/08/2025 07:07

Maybe I should also add how I currently dress. At the moment I’m mostly in balloon trousers and boxy t-shirts, which is a look I like and am very comfortable in - but it’s the antithesis of dressing for the male gaze and on this trip, I really want to look good for a man! (Please don’t judge me for this, I spent many years in a sexless marriage and it is a complete shock and joy that I’ve found someone at this stage of life that actually fancies me. I’m happy to lean into that a bit, while still staying true to my own personality - just don’t quite know what clothes to choose to do that.)

OP posts:
RemusLupinsBiggestGroupie · 17/08/2025 07:45

Have you got a pair of trainers you like and are comfortable? You’ll want them if you’re going to be doing lots of walking. Then you can work up from that for daywear eg some loose wide leg trousers, maybe a bias cut midi skirt.

For evenings, will you be wanting to stick with trainers or have you other shoes in mind? Some things will work better than others according to footwear.

lifeafterdivorce · 17/08/2025 08:20

Hi @RemusLupinsBiggestGroupie i do have trainers that I like, from community clothing. I also have quite a lot of trouser options, and a couple of good skirts (pleated midi, navy knitted maxi). It’s really dresses and tops that I don’t have.

For evening, I have a pair of dark red leather sandals that will hopefully work but would be willing to buy flats if needed (I have loafers, also boots)

oh, and I only have carry on luggage!!

OP posts:
EllatrixB · 17/08/2025 09:24

Ooh congrats OP!

A few starters for ten to help you narrow things down/rule stuff out:

Hush navy chiffon ruffle shirt, admittedly an eye-watering £90

Beaufort and Blake white broderie blouse, reduced to £49

Green floral Nobody's Child blouse with wide collar, reduced to £29

This sort of plain neutral top can be dressed up or down (although personally I wouldn't pay this for it!) - this one's from Wyse

Do you like the look of any of these? If so then that gives people an idea of what you might be going for.

Dresses-wise, I was initially going to recommend the Uniqlo Rib Jersey bras dresses for daytime but see those are out for you. How do you feel about jumpsuits? I have an excellent linen-blend sleeveless black jumpsuit from Ro & Zo that is quite useful for its versatility.

Chiffon Ruffle Blouse | Navy Blue | hush

https://www.hush-uk.com/chiffon-ruffle-blouse-navy-blue/012728-1659.html

IMissSparkling · 17/08/2025 09:26

Othersnotsomuch · 17/08/2025 06:44

Budget ?
where do you usually shop?

Can no-one read properly any more?!

Gall10 · 17/08/2025 09:29

Please don’t dress to please a man…..dress to please yourself! Self-worth is the most important attribute a woman can have. If you have self-worth you’ll have self-confidence…..there’s nothing more sexy than that!
Enjoy your time away…Hope you have a fantastic time.!

Chewbecca · 17/08/2025 09:32

I'd look at some of the outfits worn by INPO on Instagram. She always looks modern and 'put together'. I think it might be partly her accessories / jewellery - how are yours? Might be worth considering.

Chewbecca · 17/08/2025 09:33

E.g.

City break with new boyfriend after divorce - help!
Mulledjuice · 17/08/2025 10:02

I don't dismiss your premise but please remember that he already fancies you as you dress now!

lifeafterdivorce · 17/08/2025 10:04

ooh thank you @EllatrixB very helpful suggestions. The Hush and Wyse tops are definitely the kind of thing I would wear. I am currently looking at this Suzanne top, which seems dressy enough for evening but casual enough for my general? https://www.sezane.com/en-en/product/abelia-blouse/black#size-12. Jumpsuits don't work for my shape (long back) and I find them a bit awkward to wear in in-between weather where might need a coat.

I would love dress ideas, though I don't really know what I want!! Something casual and easy to wear, yet also flattering?

Thanks for the INPO suggestion @Chewbecca - it's really helpful to see outfits on someone that is closer to my size than a Sezane model!

And I do appreciate your point @Gall10 but I have plenty of self-worth (and a lot more of it since I started dating someone who is nice to me, unlike my ex-husband). It's just nice to have come through the other side of a painful divorce and be looking forward to a fun few days away - I want to enjoy dressing up a bit more than usual and feeling good in my clothes (and yes, having someone else tell me that I look good in them). That's all!

OP posts:
lifeafterdivorce · 17/08/2025 10:11

ah @Mulledjuice that's very nice of you, and yes, also true! I definitely don't want to go miles away from my normal self. Just a slightly more dressed up /less practical version (especially since I won't be doing any dog-walking for a few days....)

OP posts:
Mookie81 · 17/08/2025 12:02

Othersnotsomuch · 17/08/2025 06:44

Budget ?
where do you usually shop?

Are you being serious? Confused

Patagonia21 · 17/08/2025 12:47

For such a special holiday I would spend a day shopping in person, trying on dresses, skirts and trousers that really make you feel amazing. As well as Sezanne blouses and new underwear. It’s part of a new relationship and he will appreciate it.

I find shopping on line for blouses works but for other things it’s helpful to try on different sizes and shapes with a full length rear view mirror! sizes seem to vary so much at present

jay55 · 17/08/2025 13:33

John Lewis have masses of dresses in the sale right now.
I found this at John Lewis & Partners. What do you think?
https://www.johnlewis.com/south-beach-puff-sleeve-button-detail-midi-dress/p113112480?tmad=c&tmcampid=7&s_share=jlappios_Y29tLmFwcGxlLlVJS2l0LmFjdGl2aXR5LkNvcHlUb1Bhc3RlYm9hcmQ=

lifeafterdivorce · 17/08/2025 15:31

thank you @jay55 but I can't really pull off the puff sleeves look, though I like the shape on others. Thanks for the link to the JL sale - I've been scrolling through loads of sites in the sales but then just end up confused, or find something I love and it's not in my size.

I like this for a day dress https://www.johnlewis.com/celtic-co-check-tie-front-pure-linen-dress-rust-navy/p113073139?size=12 but will it look a bit old-fashioned and frumpy in reality? (sorry I know that's a hated MN word!)

I also like this https://www.wyselondon.com/products/simone-dress-green-woodblock-print but maybe too light for late September?

Simone Dress - Green Woodblock Print

Simone Dress - Green Woodblock Print

Meet your new favourite sundress, the Simone! A gorgeous green woodblock print, designed in-house at Wyse. Breathable and comfortable, with no compromise on style, the Simone is perfectly low maintenance and high impact for the holidays! Flattering sof...

https://www.wyselondon.com/products/simone-dress-green-woodblock-print?_gl=1*oupq6f*_up*MQ..*_ga*OTE2MjU1Nzk1LjE3NTU0MjA1NTA.*_ga_K9GVDC04ZT*czE3NTU0MjMxNzckbzIkZzAkdDE3NTU0MjMxNzckajYwJGwwJGgxOTAxNzgxNTY4

OP posts:
jay55 · 17/08/2025 15:56

The green dress is lovely. And would work on a sunny day.
The check could go either way.

jay55 · 17/08/2025 15:57

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jay55 · 17/08/2025 15:57

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RemusLupinsBiggestGroupie · 17/08/2025 17:09

How about a black jersey column dress? Can be worn with trainers or sandals and with a shirt or jacket over.

The checked dress is a no from me, sorry.

lifeafterdivorce · 17/08/2025 17:23

Ooo thank you @PickleASturgeon some great suggestions there. I might order and try…

@RemusLupinsBiggestGroupie would be open to a jersey column dress but would have to be very heavy material/with some structure - I’ve put on a bit of weight and it all seems to be going on the middle.. do you have any suggestions for one that would drape or hang well?!

OP posts:
PickleASturgeon · 17/08/2025 17:53

Glad you like them. No idea what they will be like in real life, but I thought they looked nice online. I know the brown is not a colour you specified, but thought maybe the shape would be worth a try.

Hope you have a lovely time away.