Fall & Winter Footwear for Midi Skirts and Dresses

There were questions on the forum recently about what type of footwear to wear with midi skirts and dresses for Fall and Winter. There are many, many options across flats and heels and the footwear you choose will depend on how dressy you want to look, and how much you want to elongate your leg line. The higher the heels, the longer the leg line. Personally, I choose flat and very low heels (up to an inch and a half in height).

Here’s my current collection of Fall and Winter midi skirts and dresses. The voluminous olive COS dress is a little longer on me, but not knee-covering. It’s not a true midi because of the short front, but the sides and back are longer so I treat it like a midi. The red floral dresses are knee-covering.

Here’s my assortment of Fall & Winter footwear that I wear with the above skirts and dresses. I sport sheer black hose, nude-for-me-hose and black micro fishnets with the footwear. Sometimes I wear socks with the tall boots instead of hose. There are high-shaft booties with a sleek ankle fit. Western shooties that are extremely tailored on the foot. Refined oxfords, ankle strap pumps, and classic ink blue tailored knee-high boots. TAILORED footwear is my preference. Coincidentally, all shoes have a low heel.

If you don’t get very cold feet like I do, you can wear some of the more open footwear styles I wore with warm-weather midis all Summer long. Leave off the hosiery and socks. Here are my Summer midi dresses and skirts with the shoes that I wore with them. Pointy-toe ballet flats, classic sandals, loafers, mules and white sneakers. All of the shoes here are flat.

I don’t like to wear boots that gape at the ankle or calf with midis. The fit MUST be sleek. I wear a lot of light-coloured footwear because it bookends my blonde hair and looks crisp. I also enjoy some darks, metallics and brights to change things up. Or wearing white footwear with sheer black hose to create a graphic contrast. It works well when the midis are dark, which all my Fall and Winter midis are.

I’d love to get more midis because my outfit happiness factor is through the roof when I wear them. Hands down they are my favourite item to wear in 2018 across the seasons. White jeans and fun pants are a close second.

Eloquii Hankerchief Hem Rib Midi Skirt

Eloquii Tie Neck Midi Dress

Trend: A Nod to the Wild West

I mentioned in my trend report that Western wear is getting its fashion moment. A nod to the Wild West also made my seasonal must-haves list for Fall and Winter 2018. It’s a Trendy Classic, iconic, timeless, and always in style. But because it’s fashionable at the moment, you’ll see larger and deeper assortments at retail. 

Western wear is generally an earth-toned and neutral palette, but these days pink cowboy boots are not uncommon. When I think of Western wear, cowboy boots and all sorts of variations of them are top of mind. But there’s also ornate cowboy belts, felt and straw cowboy hats, fringed anything, suede and shearling jackets, shearling vests, sheepskin, pony and cow print, plaid barn jackets, moccasins, bootcut jeans, ponchos, ruanas, tiered skirts, ruffled blouses, studded bags, saddle bags, prairie dresses, denim jackets, denim shirts, bandanas and checked shirts.

Shopbop
Tibi Felix Boots
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4
Zappos
MARC FISHER LTD Baily
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2
Zappos
Diba True Cuddle Bun
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2
Hobbs
Exotics Dress
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5
Shopbop
R13 Cowboy Dress
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3

You can interpret the trend as fully as you like, especially when you live in an area of the US where Western wear is a stylish staple. Others might prefer to add hints of Western wear to their outfits. Or remix Western items with their avant-garde, hard-edged, Preppy, Modern Retro, Punk or Sporty styles.

My clients run the gamut. Some adore Western wear, and are never without a pair of cowboy boots and bootcuts. Some like fringe, suede and denim shirts, while others are into denim jackets, ponchos, ruanas, weathered brown leather and ruffled plaid blouses. And some don’t fancy the vibe at all.

Personally, I like the irregular juxtaposition of adding a Western element to a polished, pretty, crisp, dressy and very un-rugged outfit. That’s my ‘80s gene coming through, which is why I bought a pair of optical white Western shooties at the Nordstrom Anniversary Sale this year. I LOVE these shoes, and they’ve become unexpected wardrobe workhorses. I thought I’d wear them from time to time, but instead want to wear them all the time. They’re very comfortable, and add a fresh 2018 component to my outfits. 

For example, I’ve been wearing the new white Western shooties with a few Fall midi dresses, a ruffled midi skirt, and a pair of high-waisted black skinnies. For toppers, I’ve worn my old Smythe equestrian blazer and new cape coat over the floral midi dress. I’ve worn the navy polka blazer, denim jacket and old navy Theory blazer with the navy ruffled skirt and a form-fitting top. I’ve worn the black high-rise skinnies with a tucked striped top and cape coat. In every outfit, I sported high-contrast sheer black hosiery or socks with the white Western shooties, and finished off the look with a light blue bag and white pearls. The white pearls and my blonde hair effectively bookend the white footwear. I’m enjoying the new-to-me vibe VERY much. The happiness factor is high, and here are the exact items from my wardrobe used to create the outfits.

Over to you. Will you add a nod to the Wild West to your style? If so, how do you wear the trend?

Team Mood Dresser or Team Uniform Dresser

There was an interesting discussion about mood dressing on our forum recently. The upshot was that uniform dressing is the antithesis of mood dressing. They are on opposite ends of a spectrum, with all sorts of variations in between. 

You are on Team Mood Dresser if you dress according to your current moods and emotions. For example, you’re under the weather so you choose a soft, cosy, sentimental and relaxed outfit. You’re feeling confident, positive and powerful so you choose a form-fitting dress in your best colour, killer boots, and top it off with a leopard coat. You’re feeling romantic, feminine and serene which means it’s florals, flounces, or a swooshing dress for the day. You’re feeling playful, energetic and cheeky, which means hectic pattern mixing is dead right. You’re feeling unsociable yet dramatic, so it’s back to black, black and more black. Or you’re serious, professional and intense, opting for dark, tailored and somewhat severe clothing for the day.

The second way you could be a mood dresser is by choosing an outfit to put you into the mood of choice. You might wear a tailored jeans-blazer-boots outfit because it makes you feel invincible. You wear bright colours and fun patterns to lift your spirits on a down, tired or grey day. You’re remixing stripes, florals and animal print to get your creative juices flowing for the day. You’re anxious and need a calming and soothing look, which means falling back on good old blue and white.

You’re on Team Uniform Dresser when your moods and emotions do not affect what you wear during the day, and what you wear does not impact your mood or emotions. You have a few defined outfit combinations for the season and run with them regardless of mood swings and emotions. You can plan your outfits well in advance and stick to the plan because, despite your feelings, what you wear won’t affect your mood.

Of course, both ends of the continuum are extreme and many of us would probably pick a position along the continuum instead. Which end do you tend to more? I’ll go first.

I bat for Team Mood Dresser. Unless I’m packing a travel capsule, I cannot plan a week’s outfits in advance because I need to pander to my current mood and emotions when I choose an outfit in the morning. I don’t have uniforms, and tend to mix things up a lot in silhouette and colour. My happy colours and favourite patterns effectively lift my spirits and energize me on a sad and tired day. Punchier and unusual outfit combinations arise when I’m in a creative, relaxed, care-free and spontaneous mood. I often wear a dress or skirt when I’m feeling extra confident and alluring. I wear shades of white when I’m feeling calm and high-energy. I wear brights and high-contrast neutrals when I’m feeling powerful, happy and positive, OR to make me feel powerful, happy and positive. I usually wear tonal dark outfits without high contrast when I want to blend into my surroundings, feel less social, and have a quiet day.

I’m VERY curious to hear your thoughts and preferences. Do you bat for Team Mood Dresser or Team Uniform Dresser? Tell us why and no batting for both teams. But if you can’t pick a side, feel free to hang out on the beach where I’m serving homemade cheeseless vegetarian pizza on a wholewheat base with spicy honey onions, eggplant and red peppers. Salad on the side, and strawberries and cream for dessert.

Roundups

Simpler Items

This week's list of top picks list is about basic pieces.

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Assorted Items

Items for Summer, both in and out of air conditioning.

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Casual Summer Vibes

This week's top picks are good for a casual Summer vibe.

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Summery Earth Tones

These items are for those who like to wear casual earth tones in warm and hot weather.

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Hints of Spring

Some tried-and-tested winning items to refresh your style for Spring.

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Dressier Items

An assortment of dressier top picks might be just what the doctor ordered.

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The Items I Keep But Seldom Wear

In writing about a recent closet edit, I mentioned that I kept some infrequently worn wardrobe items. They are in excellent condition, fit well, look great, and most importantly continue to spark joy when I wear them. For a variety of reasons, however, they don’t get much wear. 

I don’t worry about items that don’t get much wear, as long as I love them and feel fab wearing them. Usually, I’m very into wearing my newer items, which does mean that older items can fall by the wayside. But infrequently worn wardrobe items often come back into favour, which is why I hold onto them.

1. Skirts & Dresses

These are more formal pieces that come out from time to time. I bought them knowing they’d be worn infrequently. I’ve worn the skirt, and a few lace dresses with denim jackets to work with clients and out to dinner in the past, and enjoyed the outfits. I might do that again next year with my new pointy-toe ballet flats since I no longer wear heeled ankle strap pumps.

2. Jackets

These jackets are old, and very old. The first ten year old navy jacket is a beautiful, well-made, tailored piece that I used to wear a lot with skirts and harem pants. Then I got into longer, more fluid jackets so it fell by the wayside. The Theory blazer in navy is eight years old and fell out of favour because I went off modern classic blazers. It’s impeccable, and I knew I’d wear it again. I did just that recently when I combined it with my new flowing navy 3.1 Philip Lim high-low midi skirt. The combination feels fresh and new, and I adore it. The seafoam moto is four years old and is seldom worn because I’m no longer into leather jackets. I’ll wear it from time to time because it’s a gorgeous colour.

3. Suits

I have a funky black Summer ruched suit with cropped pants that I bought in Tokyo six years ago. It’s fitted, gorgeous fabric, unique, and looks fabulous. I’m not into wearing much black right now, although the shorter sleeves and pant hems show a good bit of skin which offsets the black. It’s somewhat sentimental so I’m never passing it on. The mood might strike me to wear it at some point, and I’m looking forward to the day.

4. Jumpsuit

I’ve had this Summer jumpsuit for four years and worn it twice. It’s the most impractical, uncomfortable, and fussy item in my wardrobe, but quite spectacular if I don’t drink fluids, dodge the loo, and keep my movements to a minimum. It’s hemmed for two inch heels which I seldom wear, so there’s that too. (Ideally, I need to have the suit hemmed for one and half inch heels). It’s a Modern Retro item with a high longevity factor so it won’t date. I see no reason to pass it on because at some point I’m going to want to wear the fun piece, even if it’s just to a ‘70s party.

5. Outerwear

I’ve had the earthy cape for three years, and knew it was an impractical Seattle topper before I committed to purchasing it. It’s too long to drive in, and not very insulating for city walking. It’s not the best item to wear indoors when I’m out and about either. That said, it’s a fun Modern Retro piece that won’t date, and I love it. I won’t be passing it on because it sparks joy staring back at me from the coat closet. My ten year old arctic Soia & Kyo puffer is immaculate, impeccable quality, and fits like a dream. I have a newer arctic Soia & Kyo puffer in ink blue that I wear instead so this one fell out of favour. I much prefer dark blue to black, so it’s a no-brainer. But the old black puffer is a very practical, quality piece that I cannot part with. And it’s good to have a spare in the coat closet.

When you have a moderately sized wardrobe, you can’t expect every item to be a workhorse, especially when there are formal and some less practical pieces in the mix. But you CAN expect every item to spark joy. As long as I have the storage space and the items fit, aren’t dated, and are in good nick, I’m keeping them.

Fashion News Roundup: September 2018

A sustainable children’s collection at H&M, a new fashion documentary series, and more news from the fashion trenches this month.

Fun Fashion Fact

Did you know that the word duffel bag refers back to the town of Duffel in Belgium, where duffel, a coarse heavy woollen material with a thick nap, has been made for more than five centuries. The duffel bag may take its name from the fabric, but it may also come from another meaning of duffel: i.e. “transportable personal belongings, equipment, and supplies.”