How to Combine Comfortable Shoes with Your Dressier Outfits


Can you please give me some ideas on footwear for Natural/Relaxed personalities that aren’t Chucks or jandals (flip-flops). Or hiking boots. But similarly nonrestrictive – no pointy toes/squashed feet.

Comfortable stylish shoes


  • With trousers look for:
    Ankle boots
    Knee high boots
  • With skirts and dresses go for:
    Knee high boots
    Ballet flats with inbuilt support (try Frankie4Footwear)
comfortable relaxed shoes


The trick with combining a comfortable, more relaxed shoe with your dressier outfits is:

  • Look for one that isn’t too chunky
  • Find one with some detail or interest (such as the leopard print examples)
  • Look for a quality leather (not fabric)
  • Low vamp shoes look best with skirts or dresses (ballet flats or knee high boots both fit the bill)
  • High vamp shoes are great with trousers.  Oxfords, loafers and ankle boots are all right in fashion at the moment.

Don’t forget about the level of refinement when choosing a shoe!


Remember that comfort doesn’t have to mean ugly!


I'm not sure if it's for you but how would you feel if you learned all about the colours and styles of clothing that suit your individual personality, shape and style? Just imagine what it would be like when you can open your wardrobe and pull together fabulous outfits that make you look and feel amazing every day? If you'd like to stop wasting money on the wrong clothes and accessories plus join an amazing bunch of very special women also on their style journey - then my 7 Steps to Style program is right for you. Find out more here.

More from Imogen Lamport

Up Up and Away in a Hot Air Balloon

Tuesday this week, my honey and I took a hot air balloon...
Read More


  • Just want to weigh in that comfy doesn’t always equal flat – sometimes the toe box is the problem (bunions) in which case “not too clunky’ can be hard to achieve. Ballet flats are not helpful as more of a heel takes pressure OFF the painful bunion area. Most comfy are Danskos, Fluevogs and the like, wide with some chunky heel or wedge, hated by many. Fortunately, those of us who wore Doc Martins with flowered dresses in the 90’s can handle it!

  • This topic is close to my heart. I have very wide feet and have been wearing orthotics since my early thirties. Low vamp shoes such as ballet flats and loafers are a no-no. So I wear Mary Janes and T-bar shoes with skirts/dresses and low-heeled boots or oxfords with trousers. I am still searching for a lovely Summer sandal. offers a variety of fashionable European brands and styles.

    The level of refinement is extremely important. Despite years of trawling the internet and visits to specialist shoe retailers I still can’t find glamorous shoes that accommodate my needs. So I wear ‘level 2 refinement’ shoes with my ‘level 1’ clothes. In fact over time I’ve begun to wear less formal business wear and wear more unique/artsy clothing so that the focus is much less on my shoes.

  • My fussy feet (wide with bunions) have become even fussier now that osteoarthritis has set in. I have the exact same problems combining shoes with dressy outfits as Ramona and Tamara. As a matter of fact, I recently went on a quest to buy some dress shoes with lower heels. I never found anything in my size that met the required level of refinement necessary to wear on really dressy occasions. Like Tamara, my clothing has to be such that the emphasis is not on my shoes. Fortunately, I was able to find stylish shoes that work for most occasions in my life, but it’s a myth that really stylish and dressy lower-heeled shoes are available in wide widths. Even on the rare occasions that I find such a gem, they’re never comfortable enough. Oh, and I have to shop online because the local stores don’t carry wide width shoes. Worse, my heels are narrower, so I can’t wear pumps; my heels slip right out of them. It’s downright depressing.

  • Im similare to the comment above me becuase I also prefer to take the focus away of my shoes Not necessary artsy, because I tends to style classic in a more creative way. You could say, Im just a rule/style breaker when it comes combining shoes to my outfits!

    Some people might find this naive/stubborn thinking (and has to do with personal preference, not critism nor trying to offending people), but personally I love the look of ankle booties or loafers with skirts/dresses, its looks “quirky”. Perhaps not in traditional/very formal enviroments, but otherwise I would wear this combo anywhere! Also regardless how formal the enviroment is, I would never jepordize my health for a pair of dress shoes. (and would your workplace or the place you going to seriously send you home because you cannot wear those “perfect” shoe choices in some countries? But I’ve come across people who think your looks/bodyshape has something to do with dress codes, like if you look too skinny or chubby in something, you are not “appropriate”, HA…which is a bit “odd”. )
    Beside, Orphodics inserts/insoles doesnt always work in my experience. I keep going back to my ECCO “nicer” walking shoes, ’cause my feets and ankles cannot handle others W/O having to take pain killers for it even if they have those orphodics insoles/inserts. (Its a bit cheezy, but people often say, if you want to dress nice, you have to endure the pain. But eating painkillers for 2~3 hour wear of a pair of dress shoes, that’s a tad over the top! I can endure blisters and tired legs but not taking medicine just to look more dressed up. -_-) My everyday/dressier shoes are about level 2 in formality, however (I often blend my shoes to my hosiery, skin or hemline and look for shoes with a more refined leather to make looks dressier), so I dont think that would cause the same “dresscode/outfit disaster” as wearing flip-flops or runner shoes to a more formal or corporate event. 😀

    But the style guide that you should wear oxfords and ankle boots with trouser, doesnt that has to do with elongating your legs rather than the dressyness of your outfit? (because the former is not an issue in my case because Ive somewhat long “chicken legs”). I prefer to use column of colors and wearing right hemlines to elongate some areas, not the shoe style

  • I posted a comment yesterday, but it’s not showing up. Basically, I have the same problems as Ramona and Tamara, and struggle to find comfortable and stylish footwear that meets the level of refinement necessary for occasions when formal attire is required. I find it downright depressing, as there is no reason why shoe manufacturers can’t make pretty shoes for those of us who have foot problems.

      • Finding shoes that meet my day-to-day fit, style and comfort requirements is challenging. It’s a safari hunt just to find my size. I don’t know what I’d do if I couldn’t shop online. Still, I’m grateful I have a collection of shoes that work for most of my outfits. Like I said, I’ve yet to find what I need for formal wear. It just doesn’t seem to be out there anywhere.

    • I agree! My ideal would be something with a low heel, comfortable sole/soft leather but made with a shiny patent leather material and/or fine detail suitable to wear to weddings, formal occasions. Have been on the lookout to no avail. Surely there is a market for such a thing? Do formal shoes have to be so painful (to those of us who wear comfy shoes 99% of the time) that you kick them off after 10 minutes and go barefoot?

  • I have had fussy feet almost all my life, and now I have osteoarthritis. Though imperfect, the best solution I have found is: low heel (not completely flat), size up and insert an insole (athletic style).

Leave a Reply

Your email address will not be published. Required fields are marked *