Dare to Wear it: High Waisted Shorts

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By fashion contributor Ashley of The Daily Bucket

{Title Picture}
With the end of summer in sight I feel like I owe a shout out to the high waisted shorts that have made an appearance this year. They can look good or bad real quick and I find myself thinking the “mom jean” look isn’t so bad. Am I going crazy? Here are a few tips to help you style your last minute short purchase (in a good way)!

{Black and White}
A good hint for pieces that are more risky is to keep it neutral. Because these shorts are in black and paired with white and nude accessories the look feels more polished and classy. Its an attention grabber, but in a good way.

{Around the City}
Keep this look fresh by wearing a loose patterned button up and a light jacket that comes down past your shorts. Pair it with some strappy sandals and you are set.

Keep reading to see two more high waisted shorts looks!

Wear to Work
For a look that is appropriate for (some) work environments choose a longer trouser short that is less form fitting. Dress it up by wearing a blazer or a tailored jacket. Peep toe platforms polish this look off.

Day at the Market- Picture of Katrina via Ashley Thalman Photography
For a simple casual look the jean short works best. Pair it with a striped tank and basic accessories. This look is all about letting the shorts do the talking.

So, what do you think? Would you dare to wear high waisted shorts?

See more in the Dare to Wear it series here


I love this look. I actually think it looks more natural than wearing jeans or pants that hit at the hips. One, high waist shorts will hide the tummy usually, and they seem to be more comfortable (for me at least). That’s just my opinion!

There is NOTHING sexier on a woman than the fashion sense of an 80 year old man from Florida! Love it!

well, i personally think they are all cute in their own way…
it all depends on your bodytype if you can pull it off, some around us will look good in it, and some will not (just like all clothes). doesn’t matter if it’s 90’s, 50’s or 20’s as long as it looks great and the person feels comfortable wearing it!

Hello, 90s, I didn’t miss you… these are ugly, unattractive, and the only reason people like them is because they’re “fashion”. The back will make you have “mom butt”.

I’m a man and I don’t like how these shorts look on a woman, they are okay
(i.e. first photo), but they’re not sexy and can’t cause lust
(you know why I’m saying this).

I can’t talk for others, but April, these girls wouldn’t call my attention
if I find them around with those clothes.

If a girl is using this, she’s not begging for attention,
she just feels well with herself.

I’m sorry I must be a spoiler here…but I really can’t believe girls go around showing this much of their bodies – and actually wanting to expose themselves. I find it difficult to wear sleeves above my elbows or dresses mid-calf, much less anything else…. Its sad to me. Girls are begging for attention from men; not saving themselves for the man who is supposed to see them and own their bodies, and even more than this, by exposing so much, and begging for attention so much, they seem to have no self-respect, no sense of privacy, and no confidence in who they really are.
Just some of my thoughts here.

Well personally I think that is a large assumption to make about women. I’m a 28 year old virgin who wears shorts and plans on waiting till marriage. Just because I wear shorts or tank tops does not mean that I’m not waiting for that special someone. I used to not wear shorts because of a lack of confidence I had with my chicken legs and it showed in my demeanor and how I held myself. So being able to finally love myself for who I am and wear shorts without fear of what people may say has given me far more confidence! 🙂

I personally love this vintage, high waisted style. I was so sick of tiny shorts style that really was just about showing lots of skin and not taking the female form into consideration.

I cannot understand how you can disrespect women by stating that they should wait for a special man to own their body????!!!! A person’s value is not based on their appearance!

What in the world are you talking about? Wearing shorts and tank tops usually has nothing to do with trying to get attention from men. They’re wearing shorts, not stripping. I agree with BTB; how does waiting for a special man to own their bodies imply that a woman has any self-respect? It has nothing to do with saving your body for that one man, and you’re implying that a woman who wears shorts will sleep with any man who notices her. If a man hoots and hollers at a woman wearing shorts and a tank top, that’s his problem, not hers. A man who does that has no respect for women, regardless of what they’re wearing.

I wear shorts in the summer, and they usually only come up a few inches above my knees. If I had the figure, I’d have no problem with wearing shorts that are a few inches shorter. I personally think these high-waisted shorts are ugly and went out of style for a reason, but that’s just me! 🙂

I think they’re great. And the high waist keeps them from looking like the “jean underwear” of my teenage years.

These girls look cute but notice how no one is showing their behind. That is where high waisted goes wrong. And let’s not forget the definition of “mom jeans”.

Yes! I love love love this look! I have one pair that’s a bit higher cut that I absolutely love. Plus it’s the panel type with three buttons on either side. Something unusual and fun!

I personally love the look, but cannot pull it off myself. I have to much of a behind! It just looks…weird on me. but keep on ladies!

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