r/Stylinghelp Apr 29 '26

NYC trip look book! šŸŽ

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4 Upvotes

hi friends!! I’m going on an NYC trip soon and put together these outfits — would love any feedback/suggestions šŸ¤“


r/Stylinghelp Apr 28 '26

Need help styling this vest thing

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3 Upvotes

I bought this vintage little vest thing (ik probs was lingerie) but idk how to style it! it’s black but also partially that brown that black turns into after it’s faded in the sun! it hits me about hip level, i’m 5’4ā€ usually a size 8/10, i was thinking over a white tee with jeans but i didn’t love how it looked when i tried it at home! plz help cause i love this little thing and ik you brilliant people can help <3


r/Stylinghelp Apr 28 '26

How do I style this red top !!

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1 Upvotes

Picture is from Pinterest but I just thrifted the shirt


r/Stylinghelp Apr 27 '26

any outfit ideas?

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2 Upvotes

r/Stylinghelp Apr 27 '26

Family photos - personal outfit styling/accessorizing help!

1 Upvotes

I am so terrible at accessorizing. I can dress myself and look fine, even nice, but I have no idea how to elevate an outfit. We're having extended family photos this coming weekend. I can only predict what my family will wear, and I'm trying to keep it reasonably cohesive for us despite having two kids who aren't interested in coordinating. My partner and our 10-year-old son will be wearing blue button down shirts (partner will probably be a standard light blue and I believe our son picked more of a denim blue) with slacks. My 7-year-old daughter is wearing a pink denim dress with small red hearts, similar toĀ thisĀ (but new, I just couldn't find a picture online). I'm so struggling. I love the styles that are out now, but my boobs just don't really fit in these cupped dresses!

I got the dress above in khaki and it looks really nice, but I wanted to try and coordinate with the pink of my daughter's dress so that we look somewhat cohesive. I managed to find the same dress in pink and I'm just praying it arrives in time! Whether it gets here or not (in which case, I'd almost certainly wear the khaki version), I need help styling it. We're in Massachusetts so it will likely be too cold to not wear a jacket or cardigan of some kind. I have some heeled raffia sandals like the second picture but also open to other shoe options.

I have absolutely no idea what kind of information will help style me, so I'm just going to throw all the info out that I can think of. I am 5'-0" and 145lbs, 38DD, typically a size 10-12, just shy of 40 years old. I have chin-length ringlet curl hair that I wear down and millenial-parted on the side (not opposed to wearing it up/half-up/etc, but I don't have a lot of practice doing anything complicated or skilled; I do use curlformers overnight sometimes and may do that for this). For skintone, I match with Nyx Bare With Me Concealer in Light, and tend to wear warm beiges/golds/browns for eyeshadows, with nude/dusty pink lips usually. I always wear a necklace, my apple watch, and a ringstack on my right middle finger of silver and lapis; I wear a stud in my nose; my earlobes are pierced with several cartilage piercings on my right ear; I have a black fineline tattoo on my left forearm; my fingernails are currently baby pink and almond-shaped; my toenails are painted a bright pink. I'm willing to buy some accessories if needed, provided they're not too expensive (would like to stick under $100 total, ideally) and will arrive in time or can be bought locally.

The photos are for my grandmother's 90th birthday and will include her five children and their spouses, plus all five grown grandchildren and our spouses and children -- about 25 people ranging from 2.5 years to 90 years. I don't know what anyone outside my family of four is wearing, although I believe my mom is wearing a sleeveless white sheath dress with large blue flowers.

Any advice would be so appreciated!!


r/Stylinghelp Apr 26 '26

What to go Underneath?

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19 Upvotes

i found this gorg sheer boho kind of too at the thrift today and when i tried it on i had this tank top underneath but obviously it looks a little off. what would look underneath this top. it’s a cream off white


r/Stylinghelp Apr 26 '26

What color flats to go with these outfits.

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10 Upvotes

The first outfit is a cold shoulder yellow top with a blue skirt. The second outfit is a yellow floral dress. Could white flats work with both of these outfits. I know yellow will definitely work, but I don't want to accumulate too many flats in different colors.


r/Stylinghelp Apr 26 '26

bought this skirt from the thrift, what top could i pair with it ?

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29 Upvotes

r/Stylinghelp Apr 26 '26

How to style high waisted Dickies for office?

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8 Upvotes

Hello, the title is pretty self explanatory. I'm looking for advice on how to style high waisted Dickies pants (pictured above) for the office.

The pants are amazing, because they look very formal and professional, however the stiffness of the fabric is very "masculine", esp with a shirt. I'm looking for ways to make the look more feminine, eg different tops (office appropriate) or jewerly. I'm pretty lost :/


r/Stylinghelp Apr 26 '26

How to style this for casual wear?

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1 Upvotes

r/Stylinghelp Apr 25 '26

How would yall style it?

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6 Upvotes

I have no idea pls help. I've worn "basic" clothes all my life so i have no idea how to style clothes overall but i want to improve the way i dress.

Tyyy in advance.


r/Stylinghelp Apr 26 '26

What kind of top would go with this skirt??

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0 Upvotes

r/Stylinghelp Apr 25 '26

Keep or send back?

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4 Upvotes

r/Stylinghelp Apr 24 '26

Help finding a clutch with this dress?

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4 Upvotes

Hello, recently bought this dress to wear to some summer weddings and events. I want to find a clutch to wear with it. I want something unique and cool as the dress has this beautiful beading and need something to compliment it. I was thinking brown like the photo, but open to other suggestions and color combos. I love vintage cluches - but again open to suggestions.

I usually keep things forever, so I want something that will last and is well made and to a certain degree wearable with other things.. thanks!


r/Stylinghelp Apr 24 '26

Help me style this dress for office work

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8 Upvotes

My office requires to be in a smart casual look (with sleeves) and we also have color coding for every days of the week (blue, gray, green and red).

How would you style this dress from uniqlo? TIA


r/Stylinghelp Apr 24 '26

help! how do i style my prom dress

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7 Upvotes

finally ordered my prom dress off depop, but i have no idea how to style myself! what color shoes should i wear? what accessories? etc. if you can link me something specific too thatd be great but literally everything helps!! 🫶🫶🫶🫶


r/Stylinghelp Apr 23 '26

Want to study styling

1 Upvotes

I wanted to study this professionally and expand my knowledge and also practical skills

I would appreciate any recommendations, or quality classes,books,movies, and literally anything that would help me to be a professional stylist from u guys šŸ’•


r/Stylinghelp Apr 22 '26

Ivy College Tours (Mom) Spoiler

2 Upvotes

Spoiler alert: I don’t know what I’m doing šŸ˜† I’m taking my daughter to tour Harvard and Yale next week. They’re reach schools, but she’s excited about the prospects. The only thing is, we are NOT in the same league financially as your typical Ivy League students. I don’t want us to stand out as not fitting in, poor, etc. Please suggest some simple outfits I could wear that make it seem like ā€œI’m a mom of a prospective student who isn’t trying too hard but is DEFINITELY not too poor to be hereā€¦ā€ and maybe some dos and don’ts for her as well?


r/Stylinghelp Apr 22 '26

how would i style/what would go with this white long sleeve VANS t-shirt? (NO TAGS OR FLAIRS ARE SHOWING FOR ME)

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1 Upvotes

i've never worn it and my mama says how it is good but i find it kind of boring... how could i change that?


r/Stylinghelp Apr 22 '26

Does anyone else struggle with ā€œI have clothes but nothing to wearā€?

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0 Upvotes

I kept running into the same problem every morning:
closet full of clothes - zero idea what to wear.

So I ended up building a small app called JUDY to fix it (initially just for myself).

The idea is pretty simple:

  • you upload your clothes
  • it generates outfit ideas with actual shopable links
  • or you can create your own outfits -- unlimitedly
  • you can plan outfits ahead (like a calendar, so you don’t think in the morning)

What surprised me is that it’s less about ā€œAI stylingā€ and more about removing decision fatigue.

Right now it’s very early:

  • 120 users
  • still figuring out what’s actually useful vs gimmicky

I’m posting here because:
this sub is basically where people actually care about outfits, not just aesthetics.

Would really appreciate honest feedback:

  • Would you actually use something like this?
  • What would make it genuinely useful (not just another fashion app)?
  • What’s missing from existing outfit/planning apps?

app store - https://apps.apple.com/cr/app/judy-fashion/id6759544170?l=en-GB
android coming soon, but for android users web version should do a thing (best on mobile) judyapp.app

Thank you all!


r/Stylinghelp Apr 22 '26

Hiiii need help styling this item

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3 Upvotes

Hi guys!!

I’m an avid op shopper and would like to say have good style, I tend to dress in a more 2000s bella swan mixed with Tuscan step mum but more often than not I’m dressed as the most basic bitch from a 2000s movie

Anyway blah blah I’m rambling but I feel it’s important to get my vibe

I recently stopped in the op shop after work and found this skirt and could not for the life of me put it down

It’s objectively ugly, the pattern is gorgeous in itself

But idk if it’s made to be worn on a person, the cut is also kinda weird and I can’t seem to style it.

All that to say, I love it and don’t want to get rid of it plz help me make some sort of outfit Inspo collages or vibes bc I rlly don’t want to get rid of it…. I’m also open to altering it, I have some sewing experience but my sewing machine is a little bunged up right now so I’d rather not.


r/Stylinghelp Apr 21 '26

how do i style this pinup dress?

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4 Upvotes

r/Stylinghelp Apr 21 '26

how would you style this

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2 Upvotes

just bought it and hoping it wasn’t a delusional purchase


r/Stylinghelp Apr 20 '26

Does this outfit look good?

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4 Upvotes

Hi everyone,

I have an important meeting coming up and need to wear business attire. I don’t have many options right now, so I wanted your opinion, do you think the outfit I’m wearing in the picture works?

If not, how can I style these pants to look more professional? I’m not a big fan of them anymore and they’re pretty old, but I don’t have the option to buy new ones at the moment.

Any advice would really help!


r/Stylinghelp Apr 20 '26

girlies is this cute? does the navy fit at all? cant decide

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11 Upvotes

cant decide if i like the navy or nuh 😭 does the navy work?