When Footwear Stops Being Comfortable

You need to know exactly what you currently have and how it fits before you can make informed decisions about what to add to your wardrobe. No shortcuts. Keeping your assessment of all wardrobe items current is especially important for footwear because our feet work very hard. 

Now is as good a time as any to edit and review your footwear collection and pass on shoes that are worn out, no longer work with your style preferences, or are uncomfortable. Do not expect footwear that was comfortable last season to be equally comfortable this season. Feet change, which is why you have to re-fit your footwear every season, or after not wearing a pair for a while. 

I don’t compromise on footwear comfort because unhappy feet ruin my day. As I recently mentioned in my style goals update, I can no longer walk comfortably in heels that are higher than an inch and a half, so I’ve had to pass on many pairs of shoes this year. But I’ve happily and frequently worn most of the shoes that I’m passing on, which makes things easier. 

The collection shows the exact styles that I’ve passed onto Dress for Success in 2017. All in reasonably good condition. With most of them the heels are too high or too heavy. I think my Timberland sneakers caused my toenails to tear because of the way they rubbed those exact spots after wearing them for a while. The gold oxfords are brand new but not returnable. They turned out to be half a size big, and I can’t get them to fit comfortably.

There are four pairs of less-than-comfortable shoes that I’m keeping. The two pairs of  booties with two inch heels are the perfect height to wear with my bell-bottom jeans and sailor trousers. They only come out at night when I sit for most of the evening, so I’ll manage. The rose gold pumps are my only occasion shoes, and therefore a temporary placeholder. I’ll pass them on when I’ve found a suitable replacement. The wedges are a sentimental purchase from Tokyo that I can’t part with just yet. I enjoy looking at the floral pumps, so for now they’ll continue to decorate my closet. 

Dressy and casual boots for Autumn and Winter are my shopping priority, and I already made great headway at the Nordstrom Anniversary Sale. As much as I try to make the right footwear decision upon purchase, there’s a bit of luck involved too. Sometimes footwear isn’t as comfortable as I thought it would be, which I find out only after I’ve committed to them and put them through their paces. Sometimes they can work with a little doctoring, stretching, padding, BodyGlide, and breaking in, which is good news. Or I simply make peace with the mistake and hope not to make it again.

What to Wear on a Long Flight

I help my clients put together their travel capsules, which means deciding exactly what they pack for a vacation or business trip. What to wear on the flight itself is one part of the discussion. For short business trip flights, clients wear work attire that can take them directly to their first meeting. For short vacation flights, clients wear a casual or smart casual outfit that works for the setting of their destination.

Selecting what to wear for a long fight is trickier. I travel frequently, and most of it means spending between 6 to 14 hours on a plane. Over the years I’ve perfected what works for me, but it’s by no means a flop-proof formula. That said, most of my clients have adopted a similar outfit strategy so it might be helpful info for you too. 

Comfort is key on the plane, but also while moving long distances in airports and dealing with public transport. So is feeling good about my appearance. I choose a casual, insulated and robust outfit with structure and polish in any colour palette. The outfit formula is the same despite the season or destination because long flights are invariably freezing and layers are practical. 

Here are the components of the outfit formula:


I wear a very comfortable pair of blue jeans. Robust, forgiving, warm, versatile, and crease resistant. I’ll wear an invisible belt to keep my jeans up because they stretch out during the flight. I don’t wear leggings or Athleisure because the look is not my cup of tea. Dresses and skirts are too breezy and I can’t walk as fast in them. Some of my clients choose stretchy Ponte pants instead of jeans. 


I always wear a camisole. All my bras are comfy so there is no need to differentiate for the flight. After that, I choose a fairly crease-resistant pullover, shirt or blouse in a fluid fit that is NOT white, and looks good untucked. It must have longer sleeves, and look polished. I don’t wear T-shirts, but have worn a striped peplum knitted top that worked well. 


I add a crease-resistant denim jacket or blazer for warmth, structure and polish. I choose a style that is sufficiently comfortable to wear throughout the flight. 


I choose a coordinating and very comfortable pair of flat booties, or fashion sneakers that I wear with socks or knee-highs. Foot coverage is important for protection and warmth. Absolutely no heels higher than an inch. I usually wear my heaviest shoes to save weight on the luggage. 

I do not believe that slip-on shoes are essential for flights so that you can slip them on and off easily at security or on the flight. It’s much more important to wear the RIGHT shoes for the trip and flight. It’s a few extra moments to take off and put them back on. No train smash. 


I wear a watch, wedding ring and specs no matter what. Sometimes I fly in my pearls. 

Scarf & Wrap

I wear a scarf that coordinates with my outfit for warmth, interest, and chic. I pack a cashmere wrap in my hand luggage to wear as a blanket on the plane. That way I don’t need to use the blankets they offer, and I’m warmer and more comfy too. 


I choose a large structured satchel in a neutral or colour. A large bag is practical because of the extra things I carry when I fly. It’s dressy and structured to create outfit polish. I don’t wear large crossbody bags, and casual bags are not my thing. I also carry the cotton drawstring sack that accompanies designer bags. I pop my wardrobe pet into it when it’s stowed under the seat during the flight to keep it pristine and clean.  


I carry lots of extras in my handbag and hand luggage to ensure my comfort. A carefully curated bag of snacks, my Kindle, noise-cancelling headphones, wet wipes, hand sanitizer, lip balm, eye drops, chewing gum, hand cream, emergency medication, glasses case, and a small make-up bag. I pack a coat in my hand luggage in Winter so that I can wear it upon arrival. 

I always style my hair, pack on the moisturizer, apply make-up, and spritz some scent like I do on any given day before I fly. I touch up before we land so that I don’t look and feel like a wreck. Fortunately, my short hair travels well so there is no need to pack a brush. 

And last, I usually wear EXACTLY the same outfit on the flight back home, which keeps things simple and effective.

Ensemble: Small Chain-Handle Shoulder Bag

I’m declaring the small chain-handle shoulder or crossbody bag THE bag of 2017. It’s extremely popular across a range of age groups, style personas, and dress codes. Dress it up or down, and create interesting juxtapositions. It’s as versatile as you want it to be. 

The ensembles here were inspired by street style I’ve seen recently. Very different vibes, but with the bag in common. Choose any colour palette and wear the chain-handle shoulder bag your way.

Faded Jeans & Cognac

Combine a pair of casual jeans with a boxy shirt and semi-tuck the front to create a hint of waist definition. Finish off the look with cognac sandals and optional belt to match. Choose a chain-handle shoulder bag in any colour. 

Fab Frock

Choose a fab dress and finish off the look with sandal booties, sandals, pumps, wrapped styles, loafers or oxfords. Add a chain-handle shoulder bag in a colour that works with the outfit. 

Cheeky Shorts

Combine a pair of short shorts with a fluid blouse. Finish off the look with a chain-handle shoulder bag and matching flat shoes, or throw on a pair of fashion sneakers that works with the palette. 

Skirt & Sneakers

Combine a casual or dressier skirt with a top that works together. Create a complement of white sneakers and chain-handle shoulder bag, and a scarf that pulls together the look. Or leave off the scarf. Add jewellery, eyewear and watch as desired.

Ensemble: Small Chain-Handle Shoulder Bag






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Fab Links from Our Members

According to this article, “athleisure is not just a trend, but a fundamental shift in how Americans dress.” Lisa confirms that she is seeing this where she lives more, and more often.

Shevia wanted to share this article about how plus-sized fashion can no longer be ignored. About time too, she says.

Sally is an excellent body image enthusiast and Angie thinks this is a great article

Fashiontern happened upon an ongoing discussion about sexist school shoes, and The Guardian reporting that a parent recently shamed Clarks for selling “flimsy” footwear for girls.

Two days later the newspaper announced that Clarks was withdrawing a school shoe called ‘Dolly Babe’ “although the equivalent boys’ shoe, ‘Leader’, is still available.”

Celebrating the Small Crossbody Bag

I’m a satchel and clutch gal, and generally not into crossbody bags. I like the visual vibe of the crossbody, but I normally find them uncomfortable on the neck and shoulder. They bruise my hips and feel cumbersome to carry on my side. But I’ve changed my mind about the crossbody after finding a very specific silhouette that works for me. 

Two years ago I came home with a darling little crossbody from Amsterdam because I loved the tomato red and the dressy gold chain-handle shoulder strap. I realized that I do like crossbody bags when they’re relatively small, structured, somewhat classic, and have some glitz factor.

Unless I’m traveling, my bag’s contents are minimal. This makes it easy to swap out my bag to suit my outfit. As long as I have my wallet, lipstick, tissues, keys and large iPhone — I’m sorted. The lightweight, small crossbody doesn’t aggravate my neck, shoulder or hips like larger styles do. It adds a relaxed urban touch to my outfits, and I enjoy being hands-free. 

Since I reached for that little red crossbody from Amsterdam a lot more than I expected (creating an effective complement with red shoes and scarf), I decided to add a couple more small crossbody bags to my handbag capsule. A dear little pet in blush to match blush loafers and belt, and a rock star in olive with guitar strap to incorporate into an olive capsule I’m creating for Fall. The exact items are represented in the collection below. 

I’m enjoying my wildcard crossbody bags. It feels good to sport something fresh for my style after years of satchels and clutches. I was in Salt Lake City for ten days earlier this month, and the small crossbody bags with dressy chain-handle straps were very popular there too. They were styled into dressy and very casual outfits, and looked fabulous. Some were sporting them with a work tote, satchel or case as their second bag. 

Who else is celebrating the small crossbody bag with me?