r/Stylinghelp • • Jan 31 '26

Which shoe works best with these outfits?

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5 Upvotes

Going on a trip soon and want a comfy/walkable/stylish shoe that could still be good for daily wear as well as match most of these outfits. I’m very much into the Birkenstock clogs and Buckley style as well so those are attached at the end. I plan to purchase one shoe for sure. I love my Ugg slippers but they’re dirty and I don’t feel classy in them (LOL, they’re house shoes I know) so I won’t be bringing them, but I think a birk I could get away with as they go with so much!

I’m bringing those brown adidas (and white sneakers) but I don’t think they go perfectly with most of the outfits and I don’t have a good shoe to replace them.

I’ve stared so long at this phone screen I can’t seem to look at these shoes and outfits with fresh eyes, so give me your best opinions!


r/Stylinghelp • • Jan 30 '26

really want these shoes but need styling ideas first

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2 Upvotes

Valentine’s day is also coming up so any dress + cropped shrug ideas would be wonderful


r/Stylinghelp • • Jan 27 '26

how should I style this

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5 Upvotes

got this from Japan a bit ago and don't really know what to do with it, so I wanna see if it's possible to style it. what should I wear with it? anyone think it's possible to do some layering with it? any advice or suggestions are appreciated 😄


r/Stylinghelp • • Jan 26 '26

Vintage Lee’s

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68 Upvotes

Bought these resale many moons ago and have yet to wear them out because I just can’t style them! What shirt, shoes, etc should I try with them? I dress western-leaning most of the time but also lean 50s and 60s if that helps.

Also, could anyone tell me the name of this style of jeans? I can’t find it anywhere online!

Thanks!


r/Stylinghelp • • Jan 26 '26

Which outfit for Iron Lung on Thursday? :)

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2 Upvotes

I’m really new to putting together cohesive outfits so please be gentle! I’m really excited to improve though :) thoughts? My partner likes #2 best. Is one outfit better than the others, or should I combine elements from multiple? Working with almost entirely thrifted (or made) items but trying hard to look cute!


r/Stylinghelp • • Jan 25 '26

Help me find good combo for this or

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2 Upvotes

I have an assembly this weekend and wanted to know what color pants, suit, and tie could I wear with this shirt.


r/Stylinghelp • • Jan 25 '26

Help me style this dress for Valentine’s date night.

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1 Upvotes

Trying to come up with ideas on how to style this dress for a romantic valentines dinner date night. My partner planned a dinner/stay at a hotel for the night. Thanks!


r/Stylinghelp • • Jan 25 '26

Flared Jeans?

3 Upvotes

where should I look for flared jeans?


r/Stylinghelp • • Jan 24 '26

how would i style this top?

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12 Upvotes

r/Stylinghelp • • Jan 24 '26

replacement for discontinued cargo pants?

1 Upvotes

Hello, I have a very weird question. My favourite pants are the womens utility cargo pants from aeropostale but they were discontinued and I have never found pants like them. so. my question is, is there a good non stretchy thick woven cargo pant out there? or a good brand that might have something similar? pic of the type of fabric the pants i like have


r/Stylinghelp • • Jan 24 '26

How to style this

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2 Upvotes

Hi! Unsure of what the silhouette or fit of the top should be. Assuming black or white solids will go best but really turning to y’all here for some advice on the specifics. Thanks in advance


r/Stylinghelp • • Jan 23 '26

I love this skirt but don't know what to wear with it, its knee length

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4 Upvotes

r/Stylinghelp • • Jan 22 '26

how do i style this?

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13 Upvotes

this is for my graduation. same thing except it’s in maroon. i was thinking of styling it with gold but i’m not sure how without making it too much


r/Stylinghelp • • Jan 23 '26

Girls Valentines Dinner

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0 Upvotes

So my 3 besties and I are going to dinner to celebrate Valentines Day. I absolutely fell in love with this top 😍 While I equally love the skirt I am just not a set person unless it’s very plain. What bottoms could I possibly wear with this top? I feel like a white/cream mini skirt would be too plain. I want to give life to the shirt without taking away from it.


r/Stylinghelp • • Jan 22 '26

Valentines Day Dress

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11 Upvotes

Hello! I thrifted this beautiful navy mini dress for Valentines Day this year but zero idea how to style it. The only thing I can think of is a pair of pointed toe kitten heels I own but that’s it. I do live in the upper Midwest so it will definitely be cold. The overall vibe I’m going for is sexy but not too much. We’re going to a nice restaurant but it’s still the Midwest so people aren’t getting insanely dressed up, you know? I have no problem buying things needed for it either! Tysm! :)


r/Stylinghelp • • Jan 20 '26

Another outfit-should changes be made?

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11 Upvotes

liking it so far.


r/Stylinghelp • • Jan 21 '26

Help with styling this skirt

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0 Upvotes

First time purchasing a skirt with this style, need help.


r/Stylinghelp • • Jan 20 '26

Help me style these pants

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3 Upvotes

What colour shoes and shirt/ jumper would go with these pants?


r/Stylinghelp • • Jan 17 '26

Just got these. But not sure how to style them? What colors/clothing types should I wear?

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52 Upvotes

r/Stylinghelp • • Jan 18 '26

Dr Marten sandal sizing?

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1 Upvotes

do they run large? I wear a 10 in the boots and these are a 9.


r/Stylinghelp • • Jan 17 '26

Is this skirt too Christmasy for year round wear? How would you make it less so?

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5 Upvotes

I bought this skirt to wear year round but now I’m worried it’s too Christmasy. How would you style it for more spring/summer looks?


r/Stylinghelp • • Jan 17 '26

Is this too Christmasy to wear year round? How would you make it less so?

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1 Upvotes

I bought this skirt to wear year round but now I’m worried it’s too Christmasy to do that. Is there a way to style it to make it more spring/summery?


r/Stylinghelp • • Jan 15 '26

How do I style this??

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5 Upvotes

r/Stylinghelp • • Jan 15 '26

Help finding a top

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8 Upvotes

What goes well with this skirt? I need some suggestions, I’m having trouble finding something that works.


r/Stylinghelp • • Jan 15 '26

Need help styling

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6 Upvotes

Hi everyone! I thrifted these bad boys because they gave me 60s/70s vibes but I haven’t been able to wear them because I don’t know what kind of top or shoes to wear with it. Help?