It is that time of year again: too hot and too cold.
It’s too hot to wear winter jackets and jeans, yet too cold to wear flip-flops and open-toed shoes.
That leads to something I call The Great Boots Dilemma. Women pair various types of boots (because it is cold) with skirts or shorts (because it is warm). I understand this idea. But beware, it can be done very wrong.
Here are some recent Great Boots Dilemma sightings on the Pearl Street Mall.
I have solicited advice from the experts that I will share below.
Flat red boots with a black skirt.
Stylist Rachael Donaldson: “The Ugg look is schlumpy and over-done, but they are practical here in Boulder and a nice break from heels. Points for them being red.”
Stylist Marian Rothschild: “This girl has great legs for boots of this height. Very shapely.”
Fashion blogger Ken Izawa:
* * *Boots over jeans and boots with a sundress.
Donaldson: “OK on the jeans girl (but can we talk about her ill-fitting jeans?). Use equestrian straps to keep your jeans tucked tightly into your boots. Short dress with lots of print and those boots break this woman into too many parts making her look a square (literally) and they don’t pay off the lightweight flounce in her dress. Pretty much a don’t.”
Rothschild: “Never wear winter boots with a sundress! You’ve just crashed two opposite seasons together. Don’t do it! And if your jeans bag around the top of the boot as they do in this photo, that means you shouldn’t be wearing those jeans inside the boot. Therefore, only wear skinny jeans inside a boot.”
Izawa:
* * *Boots and printed socks and skirt.
Donaldson: “I like it. It works because the boots are fairly simple, allowing the wearer to play a bit with the socks, and there’s a break between her socks and the skirt so she doesn’t look like she has on crazy tights.”
Rothschild: “This girl needs an honest friend or a full-length mirror. So many fashion don’ts in one picture. She’s wearing winter boots with a summer skirt and a summer bag. But the worst is the argyle socks. I’m just shakin’ my head. No, No, No!”
Izawa:
* * * Fringe boots with a pattern skirt.
Donaldson: “The dress is too busy to allow for a shoe that is also busy. Makes the wearer look messy and unsophisticated.”
Rothschild: “Hopefully she has new shoes in that bag because those ’70s moccasins need to go bye-bye.”
Izawa:
* * *Black slunchy boots over black pants.
Donaldson: “Works. The slouch in the boot balances the sleekness of the pants.”
Rothschild: “These boots are fine with these leggings, but a dress would look much better than these layered shirts; they’re too short and very ’80s looking.”
Izawa:
* * *Short-shorts with bulky boots.
Donaldson: “Shorts are a tough ‘fashion’ item to wear, so once you get past that… Um, I can’t, they’re just too short on her… OK, shorts = a wedge or summer shoes, not the has-been Ugg look. Screams ‘tragic.’”
Rothschild: “Again: Don’t mix summer and winter fashions together.”
Izawa:
* * *
Boots and a dress on a street musician.
Donaldson: “Nice look for the length and shape of her skirt.”
Rothschild: “She’s got the right idea, but these boots have seen better days; they need to be replaced.”
Izawa:
* * *Western-style boots with feminine dress.
Donaldson: “Another nice combo. It really works here: color, shape, fit, everything.”
Rothschild: “These boots look great. The heel is a wonderful height: high enough to give the foot and leg shape, but low enough to be comfortable. The height of the boot is great, too. They hit the calf in a nice place which flatters this gal’s curves. Curves are good.”
Izawa:
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