Alyson Walsh-Leather_jacket_280_hush_uk_com_drape_front_dress_399_jaeger_co_u-a-27_1442449330535
Erm, not with those shoes…

The Jaeger dress I wore in the Style Tribes photo shoot (now available HERE) has opinion-dividing credentials – the midi length, the funnel neck, the sack-shaped silhouette – but I’m a fan. And sometimes it pays to play around with proportions. Look at Balenciaga in the 1950s. Made in the UK, the dress is from the Jaeger’s new Laboratory collection; it’s also khaki green and covers my varicose veins. To me, this limited edition midi feels a little Carine Roitfeld, and very Ageless Rocker. That’s the Hush biker jacket nonchalantly slung over my shoulder, though a tuxedo jacket would work, too:

The midi dress has a relaxed shape, is comfortable to wear and could make an easy alternative to the jumpsuit; just not with those shoes. Footwear that makes you look like you’ve got something wrong with your feet is always a no-no. Much better to go for a pair of elegant heeled ankle boots, Mary Janes or trainers.

53 thoughts on “How to wear a midi dress

  1. I really love the dress although it looks more brown (here) than the moss green colour shown on the Jaeger website. I love anything midi-length! There are so many lovely frocks that are cut just above the knee – they seem to be everywhere!

    And I actually don’t mind your shoes, although heeled ankle boots would look great, I agree.

  2. Just not sure about the midi length (even on you, Alyson,and you are a stunning woman) but no, can’t make up my mind whether that dress is stylish or sack-like and dull. Now the jacket – oh yes, more of stuff like that please!

  3. I actually like the way you have styled it even the shoes. Just not keen on the dress. I might have put a belt with it either on the waist or low slung depending on figure shape.

  4. Alyson I think you look great in that dress. Fab outfit for you. But not for me. I love the look of the Lab range at Jaeger and am glad they are going down a more fashionable route. But none of it suits my colouring unfortunately! I don’t suit black, leather, muddy browns or high neck clothes like that. Never mind. Winser London ticks all the boxes for me and has some flattering midi length dresses and skirts in gorgeous colours.

  5. I like it on you a lot .
    The shoes and jacket stop it from looking like a sartorial mistake and give it edge . Trouble is heels are out for me now, and I’m not sure flats will look good especially on a petite frame.
    For me , wearing this would be about attitude: good hair and general grooming, confidence and spot on accessories . I would try a v long skinny scarf ,maybe a Hermès maxitwilly to break up the vastness of it.

  6. This is a great photo of you–specifically your hair. The dress looks good while you are standing still but I can’t help wonder in real life when you are moving about that it isn’t too much fabric. I disagree about the shoes. I think they work with the jacket providing edge, definition and a point of view.

  7. The shoes are great with that wonderful dress, and do not look like they’re correcting an orthopedic problem. I love the whole outfit. It is what I occasionally buy and do, break out of the jCrew look for a little excitement and surprise. Bravo!

  8. This dress and the crew look are a cop out. Women of a certain age are already invisible. Why make it worse? This dress shape is what has made Eileen Fischer a billionaire!
    Why be a sad sack, to coin a phrase? I usually love the looks you come up with, but I ‘m not loving this one.
    Also, please, I am tired of moto jackets!!!! somebody out there, please give us some alternatives!

    1. I agree on the dress. It, like a lot of Eileen Fisher, screams, “I give up.” Sad, shapeless clothes for forgotten women. As Nora Ephron said (paraphrase), There used to be store called the Forgotten Woman. Now that I am that forgotten woman, the store has gone out of business. How ironic is that?
      What’s worse is the color of the above dress looks charitably like a brown paper bag or, less kindly, like a soiled diaper.
      I love black leather jackets, but I think I am over the hardware affectation.

    2. Are you an affionado of fancy -dress style beloved by many female bloggers of a ‘certain age ‘ [ hate that expression , let’s call it over 50 ]
      I see that as fancy dress style and an expression of a huge desire to be seen .
      There ‘s so much about fashion I would forbid if I were the fashion police, but this dress is not one of them .

  9. Yes, short boots would be smashing with that dress. I like the dress, but I’m not crazy about the color or the great expanse of plainness. I’d love to see this with a different knit pattern somewhere just to add interest.

  10. Love everything about that dress – shape, fabric, colour, length. You and the dress look gorgeous together. When did Balenciaga ever go wrong?
    As I am a sewista, I have just the right piece of fabric and the know-how. I shall make one for myself.

  11. I think you look lovely here: understated and chic. The shoes look perfect with the rest of the outfit, though I’m not sure they look terribly comfortable if you have to walk anywhere…

  12. Alyson, you did warn that this dress has “opinion-dividing credentials” – wow, you called that one well and truly!

  13. Love the dress, the shape and the color. It just needs to be about 4-5 inches shorter. The addition of a flattering ankle boot would make all the difference. I agree these shoes are not great. This is a modern shape and it looks hip and young, not Eileen Fisher as others have noted. By the way your hair and makeup look great in this shoot too.

  14. I bought a similar cashmere (but knee length dress) from Jaegar last year. Loved it from the front and then looked how it appeared at the back. Too shapeless. The French apparently always tell you always to check your back before you go out. Try it and see what I mean. On a positive note, it is very comfortable!

  15. This is the most unflattering dress I have seen recently. The words ‘sad sack’ spring to mind. Jaeger have made a huge mistake with this one. I do wear Jaeger,but I would never wear this.Alyson, you look quite good in this unforgiving outfit, but you have the height to carry it off.

  16. This dress is absolutely beautiful, I love the colour and the cut, an the neck line! I have to find it for myself 🙂 you look stunning, the edgy biker jacket goes so well with this look. It was real pleasure to meet you this weekend 🙂 hugs x Beata

  17. No. Just no. That dress can only look good on a very tall woman with an ample bosom and behind to give it shape. The shoes are ghastly. I have no idea who started that shoe style but they don’t really look good on anyone. Shoes should enhance one’s leg line, not make the feet look like they were pinned on as an after thought. The same goes for shoes with ankle straps. Unless you have very thin legs, they make your feet look like they were an after thought. At the very least the dress needs a low-slung belt, pumps and some color at the neck.

  18. Dress colour, if accurate, is good with your hair colour. Dress style is just awful. Shoes ditto. Leather jackets can be wonderful but biker jackets are for bikers and the younger age group.

    Are you going to cover Marks & Spencer’s sustainable clothing selection?

  19. Absolutely love the dress and the colour ( though sadly I couldn’t find it on the Jaeger website) but I’m thinking, bare legs in the UK autumn/winter? I realise that black tights are a fashionista ‘nono’ but seriously what would you really wear on your legs with that length dress in cold weather?

  20. I’m going to choose to see Rick Owens Fabulosity in this, rather than Sad Sack I Give Up. Add some tall heeled skinny boots, and you’re there, especially paired with that rockin’ jacket. And although I’m a brunette, I’m taking a photo of your haircut and color to my gal in two weeks and going: THIS. Only with caramel highlights instead of blonde.

  21. I love it! I have a wonderful European Style linen midi dress I am dying to wear I feel wonderful in it – I just have to find the right place to wear it.

  22. I love how you’ve styled it – you’ve made a shapeless potato sack look cool. But you could do better!!! Something with SOME shape! Unless you’re going for a true man repeller look?

  23. You look brilliant, Alyson, love the edgy look! Shoes are just OK, but the overall look it super. I’m 5’5″ so would shorten the dress and wear short boots with a heel.

  24. You are a very brave lady to model this awful dress. Dreadful colour, dreadful shape (what shape?), dreadful length. Something of the Emperor’s New Clothes about this one. However, you have made the best of a very bad dress as your hair and makeup is immaculate.

  25. I love a sack dress (having no discernible waist) but the high neck makes this one hard to wear – such an unbroken expanse at the front. You look good in it, though.

  26. I love midi skirts or dresses, but not sacks — I’m old enough to have seen the look come & (blessedly) go at least twice in my lifetime, and I don’t think they flatter any shape or size (although I must say, Alyson, that you ROCK the look in this photo!). I’ve always worn them with high boots or black leggings/shoes and either a short jacket, or a very long jacket to emphasise the long, lean look of the profile. I have one midi left after my (maybe overly enthusiastic) post-retirement purge, a black knit midi that moves wonderfully. I have always worn it with a longer-length black turtle-neck, high black (or red) boots, a loose leather belt (black or red) & an array of long necklaces/pendants — all aimed at emphasizing the over-all sense of length. Interestingly, my shortest black leather biker jacket looks really good with this skirt as well. But the sack? Nope. I don’t think any woman, regardless of her height, shape or body size, is favoured by wearing a sack.

  27. That on me would be a big NO-NO. I’m short and that length would definitely not work. I too like to see a little more shape for a female and those shoes…. ACK! No way with this dress. But that’s just my opinion. Love so many of the other things I’ve seen you in 🙂

  28. This is relaxed, casual, effortless look with amazing loose dress and structured jacket – very contemporary. Love that it’s not fussy with jewellery or accessories – clean and minimalistic. I do wear same cut dress with gold “pool slides”, oxfords or trainers and leather jacket. I think this length is great for trainers or low heels – shorter dress would not complement calves and overall proportion.
    Fashion is not necessarily about showing off your assets (especially on daily run), it’s about creating a proportionate silhouette – a relaxed, fit or dramatic.

  29. As work wear for a middle aged office manager it’s just fine but “rocker”? Seriously? Where’s the attitude? The edge? The sass? This old rocker certainly can’t see any from where I’m sitting.
    That dress needs to be shortened by at least a foot and a half and the I-don’t-do-public-transport shoes replaced with chunky ankle boots. Opaque tights would hide the varicose veins! Where’s the black eye liner and the jewellery?
    I’m sorry, a pristine black leather jacket costing more than the average family holiday is the sartorial equivalent of a bank manager going out and buying himself a Harley on his 50th birthday. A mid-life crisis. A true rocker’s leather jacket needs to look like it’s had a life. Money can’t buy authenticity.

  30. Well I love it if you love it! I think you rock it cos you love it, but in all truth it really doesn’t matter what I think or anyone else for that matter! There’ll always be people who hate our choices so best to ignore! True freedom is trusting oneself to feel good and I think you do a great job Alyson. Carry on being YOU! X

  31. Ruth: . Your comment “There will always be people who hate our choices so best to ignore!” would seem to completely invalidate the reason for a comment section. So are all the people who responded negatively to this dress “to be ignored”?
    Alyson appears to be the type of woman who can cope with remarks positive or negative. In fact, I rather think she welcomes a variety of opinions. After all, criticism can be constructive and we can all learn from it.

  32. Most entertained by the strength of feeling generated by this post!! Somewhat distressed by all the remarks about Eileen Fisher clothing screaming I give up or sad sack or similar. I like to think I’m a little edgy in my style ( ageless/aging rocker with scandinista tendencies) little did I think that a liking for E F knitwear was tantamount to shopping Eastex or Country Casuals! Perhaps they have a different vibe in the US?

  33. I absolutely love the look. Styles always look best on someone taller than 5’2″…need styles for the over 50 petite.

  34. Alyson, you look great in this because you have the height and slimness to carry the style, rather than anyone over a size 12 uk and/ or under 5 ft 8, who I suspect would look like they are wearing it to, unsuccessfully, hide their body. For me, this veers into Eileen Fisher sack territory. We could have a whole separate discussion on why EF keeps getting mentioned………

  35. I think you look super cool — great outfit. I do agree that fashion-forward flat shoes or ankle boots (maybe higher-shaft sock boots) would look even better. Wearing any footwear that isn’t totally current or fashion forward would be bad. Avoid conventional/classic heels with a look like this.

  36. No! No!! No!!! This “style” is what I’d call a “shoplifter special!” That is it’s only worth wearing if that I what you intend to do..! Neither the colour or the length work, either- it’s simply not worth wearing!

  37. Oh Lord….even on a thin woman like you this outfit is a disaster. Keep the shoes and jacket, but switch out that potato sack!

  38. No no no no. You look so pretty and fresh… and then the dress?! No no no no no. I don’t care what Balenciaga did… it was a bad idea then and a bad idea now.

  39. I think it’s wonderful. I’ve been thinking about this issue a lot lately, that is, about the whole concept of what’s “flattering” and what women our age will get the most mileage out of, clothing wise. More and more I’m coming to the conclusion that the whole point is to bring attention to our faces, and this outfit does that beautifully. Plus, it creates a long unbroken line. I think it is flattering because it draws attention to the face — which houses the brain — so who cares if it’s “flattering” in the more pedestrian sense? I think we’re really all old enough now to seriously question why we cling to the idea of what’s the most “flattering” to our bodies, and why that default-translates to something that reveals our shapes. Do we really want men (or anyone else) to be checking out our asses and boobs anyway?

    I have come to believe that we’ve all forgotten where the whole Tom Ford/skintight bandage dress/vicious high heels look came from — hookers. It’s just become so ubiquitous that we stop seeing it that way. I know that at first I might sound like a fundamentalist or super-conservative and prissy, but I assure you I am none of those things. It’s the idea that we’ve reached an age where our experience and accumulated wisdom should be the focus. But having said that, like many women my age, I have slim legs and arms and a not-so-slim belly, so this look works great for me. Even if it didn’t, I think fabrics that skim the body rather than cling to it are almost always more attractive for our cohort.

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