Trend Talk. How to Wear the High-Waisted Skirt This Fall. Second City Style Fashion Blog

Second City Style has been asked how to properly wear the high-waisted skirt trend that’s hot for fall. Let’s start with those who may want to avoid it. If you have a large chest, be careful. The last thing you want is the top of the skirt to serve as a shelf for your chest (remember this awful picture of Jessica Simpson from the summer?) and if you have a short torso, this look may only make you appear shorter.

Jessica Simpson’s bummer summer mishap

Moving on, this is a great style if you want your waist appear smaller (and who doesn’t?) and hide larger hips, thereby creating an hourglass shape. Notice most of the skirts are black or a very dark color? There is a good reason, black is slimming. If you have a killer body then bring on the red! However, if you have some problem areas, stick with the dark colors.

If you do not want to draw attention to your backside, stick with wool fabrics which are more forgiving than shinny stretch materials.

I prefer a great blouse tucked in. However, a belted jacket can look spectacular as well. Black opaque tights help create a long, lean line. Here are some stunning examples of looks to re-create.


Fendi High-Waisted Pencil Skirt $575 Net-a-Porter


Orlando Espinoza Skirt ($290) & Raglan Sleeve Top ($275) Second City Store


Escada Metallic Cape ($2,050) & Velvet Pencil Skirt ($650) at Neiman Marcus

Philosophy di Alberta Ferretti High Waisted Pencil Skirt ($495) & Puffed Sleeved Sweater ($395) Neiman Marcus

Some high-waisted skirt suggestions:


D&G Dolce & Gabbana High Waist Stretch Satin Skirt
$275 Nordstrom


Robert Rodriguez
High-Waist Skirt $264 eLUXURY

Theory Hollyann Belted Skirt $245 Shopbop


Nanette Lepore ‘Palette’ Skirt
$230 Nordstrom

L’Wren Scott Stretch Pencil Skirt $1,213 Net-a-Porter

Classiques Entierยฎ High Waist Skirt $128 Nordstrom

– Lauren Dimet Waters

5 thoughts on “Trend Talk. How to Wear the High-Waisted Skirt This Fall. Second City Style Fashion Blog”

  1. Wow, all of these are so cute.
    However, a little out of my price range. Are there any cute but less expensive versions of this hot trend??
    t-strap sandals? I know their season is pretty much dead but I really want to snag a pair of those too.
    fashionable yet price-concious

  2. Hannah,
    So I took your challenge and added one skirt that was under $150. I searched high and low, but to be honest the less expensive ones either looked cheap (which is bad) or were pencil skirts, but not high-waisted. I’m sure this style will trickle down to the mass production outlets like H&M and Forever21, but be careful that the skirt doesn’t ‘look cheap’…which judging by what I saw isn’t going to be too easy to find ๐Ÿ™‚

  3. wow thanks
    that new one on there is super cute (and just in my price budget)
    any updates on the t-straps? (again keep my price-conscious self in mind!)


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