Ask Allie: How to Style a Denim Skirt for Fall

I bought this denim skirt and this summer I wore it with a T and TOMS but I don’t really know how to wear it now that it’s getting cold without looking like a school teacher. Advice?

Denim skirts are one of those items that seem like a perfect wardrobe staple, but once you have it you realize it’s quite hard to style without looking dated or costumey. A few tips on how to style a denim skirt like this and have it look modern, fresh, and not at all like a school teacher.

This is not the denim skirt you may have worn in the early ‘00s. Back then, I had several denim skirts: distressed, dark and narrow, a-line and short, and everything in between. I went two ways, Lita Ford (would wear with engineer boots and a band tee or tank), or Faux Professional (with a blazer or ribbed turtleneck and knee-high heeled boots… and sometimes fishnets). This go-round with denim skirts, neither is really the trend. The goal, as it has been with fashion for a few seasons, is a bit of a juxtaposition. Hard with soft, dressy with dressed down. This should be in mind when styling your denim skirt.

How to wear double denim denim skirt shirt

This first look has become the hottest way to rock a denim skirt, thanks to Rihanna. Seen this summer wearing double denim with a leather baseball cap and pumps, this is a great way to make a denim skirt look modern and fresh. To make the look better for the cooling temps and to balance the distressed denim, I paired the look with tough black leather ankle booties and a leather wrap bracelet.  Throw a leather moto jacket over it when the temps drop even more.

what to wear denim skirt fall winter

A true juxtaposition is pairing beat up denim with luxurious silk. Balance the roughness of the skirt with a blouse with feminine details. Ruffles, puffed sleeves, or a pussy bow is the perfect pairing; elegant croco pumps and a leopard clutch continue the juxtaposition, making the styling obviously purposeful.

how to style denim skirt fall winter

This final look is the cool weather version of what you’ve been wearing all summer. Switch out the tee for a chunky cableknit sweater or a chic sweatshirt and the TOMS for sturdy boots for a cooler weather casual look that’s high on style and current trends.

Instead of treating a denim skirt like your jeans or denim shirt, consider it an embellished or creative fabric piece. Instead of having the top be the feature, keep the colors neutral so the skirt can take the spotlight.  By changing your outlook on the classic denim skirt, you’ll find so many new ways to style it in a modern way!

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The Sartorial Security Blanket

Fall has officially arrived in the DC area. Last week I came home from work and went upstairs to change out of my work clothes. I slipped on some boyfriend jeans and fuzzy socks (I know, the fashion quotient going on is THROUGH THE ROOF), but it was so chilly I needed another layer. To add to the high fashion of the look, I went to the closet to grab an oversized cardigan or shawl. I first reached for my ivory crocheted fringed shawl, a $12 special from Ross. A mix between something boho cool and something that smells like cat pee and sits on the back of your Great Aunt’s floral sofa, I wore the heck out of it last winter with distressed jeans, boots, and band tees.


The shawl, worn last winter, and then a selfie after leaving the emergency room in February.

But then I remembered how I wore this shawl so much of the time my arm was broken because it didn’t have sleeves and I could throw it on even when in a sling. Almost every day I wore that shawl as a cardigan, a coat, a napping blanket. I grabbed the hanger and could smell that very specific smell of hospital, even though I’ve laundered the shawl several times since that day in the emergency room, the day of my first surgery, and so many appointments after.  But it’s so cozy, and the fringe is so fun, and it’s so easy to throw on…

my fathers sweater2005, wearing my dad’s sweater

I have a sweater that I haven’t worn for years, but will never get rid of. It’s a blue and magenta marled ribbed turtleneck without any labels; I don’t even know what is the front and what is the back. The sweater belonged to my father, and I have many Instamatic photos of him wearing this sweater in New York, Russia, London, and my childhood home. Come high school, my dad let me wear the sweater and I eventually took it over as my own. I remember one of the last few days my dad was alive, he was in an out of consciousness and clarity in the ICU and I came to visit him. I took his hand, he opened his eyes, looked at me, said, “Nice sweater, kid,” winked, and then closed his eyes. I was wearing his turtleneck and that was the last time the two of us connected.

When I used to do closet clean-outs, the biggest disagreement would come with the “Security Blanket” garments. Clients would tell me that they wouldn’t, they COULDN’T get rid of ugly, unflattering, damaged, wrong-size and dust-covered unworn clothing because of the memories associated with them. Threadbare flannel shirts, stained sweatpants with holes in the crotch, dated too-small suits from their first job interview, ugly ill-fitting dresses from a first date or courtroom appearance, grandma’s quilted floral bathrobe. I thought it was ridiculous, clothing is just clothing. Memories come from experiences, not from their ex-husband’s Grateful Dead tee shirt or their mother’s Christmas sweater.

But what a hypocrite I was, asking people to toss sartorial memories when I had my dad’s sweater in my wardrobe. So maybe at the time the sweater fit well and looked cool and relatively classic, would I toss it if it wasn’t? Now several sizes larger and trends very different I haven’t tossed the sweater and I never would. But my “Broken Arm Shawl,” that’s another story.

If you’re reading this blog, it’s likely because you care about clothing in an emotional way. It may be a certain designer, or how it your clothes help express your passion or personality, or because it can transform your figure or your career, or because it represents your faith, your culture, your community. Maybe you find style a mystery and are trying to figure it out. Clothing has energy, clothing can change your mood, clothing can change your life. And if you feel this way, you likely have a sartorial security blanket or two in your wardrobe.

I’m not going to suggest you toss these security blankets, but ask you to think about what memories, and what energy is associated with the garments. If the memories associated with a garment are good, well maybe it’s worth to keep it. Honestly, it’s not so bad to have a dust collector in the back of the closet if they make you feel good and remind you of good times and good people. But be honest with yourself regarding those memories, and why you’re holding on to the item. Don’t let the negative energy of a garment hold you in the past and hold you back.  I’m getting rid of the “Broken Arm Shawl,” coziness isn’t worth the illness, pain, and sadness associated with it.  Life’s too short to wear things that make you miserable or remind you of misery.

I encourage you to join me and get rid of any clothes associated with heartbreak, injury, illness, death, pain, or sadness. Donate it or ceremonially burn it, just get it gone from your life. Quality, not quantity, even when it comes to the emotional hold-ons collecting dust in the very back of your closet. You deserve a wardrobe that makes you feel, as well as look beautiful.

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Comfy and Chic Boots for Fall: The Chelsea Boot

I can’t wear more than a 1” heel and need a new shoe for fall. I’m looking for something I can wear with pants and jeans to work and home.

I can’t keep up with trends, can you suggest a shoe for fall and winter that won’t be tacky next year? I don’t have to dress up much at work, I wear a lot of casual pants and sometimes leggings with tunics or dresses.

I have an answer for both of you – the Chelsea boot. A classic short boot that has been chic for years and likely will be for many to come, this boot is quite popular this fall making it easy to find in a variety of colors, styles, and pricepoints. Also known as jodhpur boots or Australian work boots, this style of boot has been around since the Victorian period, so you know it won’t go out of style any time soon.

Chelsea boots are made to be easy to slip on, with their signature elastic gussets on the side and a pull tab on the back. While such boots are obviously styled with trousers and jeans, current trends show Chelsea boots slipped over skinny jeans and leggings or styled with tights and skirts. It’s refreshing when current trends are classic AND comfortable! A few favorites I’ve found on the web:
comfortable stylish low heel shoe for fall winter
1. Trotters ‘Leah’ Chelsea boot is of supple leather with a rubber footbed, making it comfortable and flexible. Available in narrow, medium, and wide widths as well as two classic colors (black and cognac), this is a great choice for the fussy foot who wants chic style. $144.95

2. For you heel-aholics, there’s a Chelsea boot for you too! I’m drawn to the ‘Zane’ from Chinese Laundry with its stacked wood heel and scalloped shape at the elastic. Cognac would look great with distressed denim, and the black and wood combination would look fantastic in winter with a chunky turtleneck, a-line mini and thick tights. $119.95

3. For those who like to make a statement with their feet, the ‘Meow’ from Ganni Veronica is perfect for you! A tan and black leopard print on leather will complement much of your wardrobe and a wood heel keeps it fun and fashionable. $342.77

4. A Chelsea boot doesn’t have to be of glossy leather, and the ‘Aimee’ from Naughty Monkey shows that a slouchy suede Chelsea can be quite chic. Available in black, tan and taupe, this is a bootie that would look best with casual looks, be it boyfriend jeans or wool tights and a dress. $79.95

5. Want to take full advantage of the chunky soles and heels that are back on the scene this season? Then you may like the ‘Alter Ego’ Chelsea from ASOS. While the sole is trendy, the rest of the styling is classic, making it a good choice if you plan to incorporate the chunky shoe into your long-term personal style. $104.74

6. Why keep the Chelsea boot to classic footwear, when it’s such a wearable style? The Chelsea makes for a great pair of rain boots, as evidenced by the ‘Crain’ by Aldo. Available in black and brown rubber, it’s a smarter workweek choice than candy-colored knee-high wellies. $50.00

7. Cole Haan is my go-to for classic and elegant work shoes. Their ‘Draven’ Chelsea boot is no exception with a higher but still wearable heel and classic lines. While it’s available in basic black and brown for work or play, the Maple Sugar Suede would pair beautifully with a cream fisherman’s sweater and distressed skinny jeans. $298.00

8. The ‘Ava’ from Paul Green is one of my favorites because it has a fun spin on the classic Chelsea. With a medallion stamped toe box, the shoe stands out in a crowd but is still conservative enough for the workplace. Available in black, Cuoio (a light cognac), and Truffle (a taupe that would look great with brown, black, or gray). $365.00

9. Can’t go wrong with a classic! The ‘90s are back, so no better time to get your Doc Martens fix with their ‘Flora’ Chelsea boot. A low heel and DM’s well-known quality, these are available in a polished black leather that will only get better with wear and time. $139.95

10. For those who desire little to no heel, the Brogued Chelsea Boot from Boden are a great choice. Available in black, Red (which looks more like Cordovan to me), or Navy, this boot would look great for the office but also adorable with skirts and dresses. $198.00

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