| Where are you going in this outfit? A backyard BBQ, grocery store or out to dinner? Short shorts aren’t my thing, so pay attention to the leg length (measure from shorts hem to crotch). Measure the shorts you currently own to determine your ideal length. |
Honestly, the first two shorts look like what my ex bil, who is a hill billy, used to wear in the 90's when he was in his 20's. Before the confederate flag tattoo, but after becoming a teenaged father. |
| I hate wearing shorts and I've started wearing casual dresses most of the time. They're so comfortable. |
The third link is just a normal, not "big and flows" pair of linen drawstring pants. Also, having bough Gap Factory stuff before, they will almost certainly shrink and be an inch or two shorter after you wash them. Those are middle aged mom pants if I ever saw them, and will look fine with a regular t shirt or tank. The Uniqlo pants are more voluminous but I'd have to try them on. I have a pair of poplin drawstring pants that are a similar shape (I think from Banana Republic) and they are very flattering. I wear them with linen shirt, sometimes tucked sometimes not, and a pair of slide sandals, and it's a very easy and comfortable hot weather outfit that also looks pulled together (and will work for a casual office even). |
Honestly, the first two shorts look like what my ex bil, who is a hill billy, used to wear in the 90's when he was in his 20's. Before the confederate flag tattoo, but after becoming a teenaged father.
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Same all shorts give me a wedgie, even the "long" ones. I go to skorts (biker shorts which don't give a wedgie) covered up by a skirt, so that people don't pass out just looking at me in biker shorts. Also with dresses I wear biker shorts underneath too! |
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Bermuda shorts are a thing this year. I think if you are over 30, you need to wear a more polished version, like this:
https://www2.hm.com/en_us/productpage.1331872002.html Not the baggy, masculine ones. |
| The issue with skorts is that they tend to be too short. |
What type of shoes though? That's what I struggle with. I have a long torso with short legs and longer shorts just make my legs look stubbier. |
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I like linen shorts. I have pairs from Marine Layer and JCrew that hit mid-thigh (probably a 5" seam if I had to guess; not super short). I also like linen pants and dresses in the summer.
If I'm going to be active, I'll wear a skort from Athleta. |
Yeah, there's no way I'd wear those shorts unless I was wearing wedges or a sandal with a heel. I'd look like a frump otherwise. |
If they have a higher waist, they will elongate the leg. I also have a long torso with short legs. I wear mine with flat sandals most of the time. I don't like how they work with sneakers. |