28 Comments

Thank you for this ! I never know what to wear with denim cut shorts in Town! I'm afraid I'm too old to wear it and at the same time... I don't care!

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I'm getting there too! Starting to feel like I'm aging out jean shorts, but I am determined to figure out a solve!

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You are still young... I am almost 50 years old my darling .... Total despair 😂😂😂🙃🙃🙃🙃

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Valerie, good to know you're here! I'm 52, for crying out loud. I still have denim shorts because I literally cannot find anything else. The longer shorts require a heel (I think?), which I'm not against if they're comfortable and not too high. I wear said denim shorts only out of pure necessity.

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I truly believe you are never too old to wear shorts as long as you feel like doing it! As stated by my mom who is wears shorts in the city at 59 years old. She tells everyone is good for your legs health and I second that! They enjoy the sun and the air in the city

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Yes, very true! I actually love denim shorts, I love denim anything, but I feel too casually dressed. They are often ripped and distressed, so yes, I feel like I'm trying to look like a teenager. But Leandra has provided some excellent styling advice here so there's much hope!

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Q: How old is too old?? (Asking for a friend...)

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EXCELLENT question !!!!!!! All is in the head !!!!

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I actually find I’m more ballsy about what I wear the older I get… 😂 maybe not older and wiser tho?!

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I love this sentiment. I reject the possibility that you can be aged out of any particular garments but welcome the idea that you might decide you've grown out of a certain look. With denim shorts, I'm fairly confident we have lightyears of time, no matter how old or young we are to make them work. They're like sandwich bread!

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Whew, really took myself on a headspace journey from yday's perspective on aging out to today's on growing out. Semantics, man.

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Agreed! And I’m delighted with your suggestion of wearing them with a neat little jacket - revolutionary, thank you!

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a neat little jacket - revolutionary ! I m agree with you !!!!!!

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Loved your bag post today! Didn’t know where to comment on it. Can you give an recommendations on how to find cool bags on Etsy or other sites? Vintage? Thanks!!

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Do you find The Constance sandals by The Row comfortable?

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I do, yeah. Mine are the flat ones which probably helps and the sling back stays up which is often my main frustration point

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Great post and thank you! I wear denim cut offs (I am 59!) and love how you put these looks together! Looking for slingbacks now. Thank you so much.

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I just took a pair of my hub's jeans and did a straight cut-off and then washed & dried them with a wet towel. voila~Perfecto! Gave them the perfect fray and the leg opening worked better for my muscular legs than most women's cut-offs do. Thanks for this post. Always a struggle to figure out how to dress casually in the summer without looking like every past year version of your-self.

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Fantastic post, Leandra! I'm not sure I can wait for Thursday's post - words cannot describe how dire my shoe situation is.

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What’s your biggest sandal problem right now?

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I feel like a slob in the summer. I vastly prefer jeans and light summer pants which are casual, obviously. So I'm thinking shoes would help me feel less slobby but I need to be able to walk comfortably during the day. I'm open to a comfortable heel! I'm open to anything, quite frankly. I'm ridiculously obsessed with denim so I wear it in the evening too. Comfort less of a concern here but walking comfortably, not tottering around and covered in blisters, would be awfully nice! Thank you so much!

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You are singing my siren song!!! All about a refined, practical shoe. I got you

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I think I mean swan song?

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Ha! Well, it’s truly an emergency situation so siren works well. You put it far more succinctly than I, however.

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I'm also interested in sandals or other summer shoes that are comfy and easy to put on *and* are fancy enough to elevate a casual summer outfit.

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Agree about the age. But with the jacket and shirt, it’s doable. Loooove this article and all the others. Thank you Leandra.

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So true ! And useful !

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