Closet Confessions: How I Dress For Myself On A Date | Fashion Haul | Trinny

This is really about rediscovering your femininity and sensuality through the lens of an outfit. For today’s Closet Confessions, I’ve been contemplating the woman I am today how that might translate into my date-night wardrobe. For me, that means swapping out the chunky boots and trainers I wear as part of my day-to-day businesswoman attire and opting for a sexy heel instead. Whatever makes you feel like the best version of yourself, use it as inspiration for your next date-night outfit…
Take a whistle-stop tour through Trinny Woodall’s (fifteen) wardrobes with Closet Confessions. In each episode, Trinny deep-dives into a particular section of her closet, mixing high street, vintage, designer and everything in between. This is everything you’ve ever wanted to know about fashion and styling, from the expert herself.
Makeup all Trinny London, shop the range here
trinny.co/dressing-for-a-date
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BFF All Day in Sophie
Sheer Shimmer in Katie
Flush Blush in Reem
Black high-heeled boots: Prada
Black cowboy boots: Prada
Silver heels: Valentino
Giraffe print heels: Manolo Blahnik
Transparent leopard print heels: Alaïa
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Navy jacket and trousers: Celine
Navy sleeveless layering piece: COS
Silver cuffs: Tiffany & Co.
Pearl necklace: Chanel
Long silver necklace: Felt
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Navy V-neck jersey top: Acne
Navy trousers with front pleat: ME+EM
Drop necklace: Dries Van Noten
Constellation-print cape: Valentino
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Black pleated skirt Comms des Garçons
Long-sleeved puff-shoulder black top: Isabel Marant
Black heart heels: Alaïa
Black pom-pom coat: Joanne Hynes
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Black and white dress with gold floral appliqués: vintage Prada
Gold heels: ME+EM
Eye2Eye in Dawn
Eye2Eye in Universe
Eye2Eye in Emperor
Sheer Shimmer in Maiko
Sheer Shimmer in Dido
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Black balloon-hem mini dress: Alaïa
Long navy coat: Dries Van Noten
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Long leaf detail gilets in black and gold: James Lakeland Luxury
Black bejewelled belt: Zara
Black trousers: ME+EM
Gold clutch: Chanel

[@brookenankin6477]

Trinny! That was me that you met in Melbourne who had the cape recreated! Shout-out to my "Esuzanah", Nelli, who played a very major part in the making of it. I'm thrilled to bits you remember me xx❤

[@alamedadanceparty]

Amazing!!!! ❤❤❤

[@lauras7805]

Can we still get it or something similar? If so where?

[@brookenankin6477]

@@lauras7805 Google "Valentino Constellation Cape" and save some pictures to do a reverse image search to see if anybody is selling anything similar. I used a navy Zara cape as my base and bought un-freyable fabrics like faux suede and pvc to cut out my appliques.

[@EsteeWalts]

She most probably will not give a reaction. She is obsessed with clothing and rubbing her face at least twenty times a day , that's all.

[@muoian]

6:03 this pearl story is everything!

[@TaniaMcCartney]

Some beautiful options but those two leather leaf dresses are some of the most exquisite pieces I’ve ever seen. OMG, the envy! They are beyond, and you look just incredible in them. Please please pleeeeease do a CC on them x

[@tonirose6776]

Have to agree: the leather leaf dresses are absolutely gorgeous, sexy, yet sophisticated! Never seen some piece of clothing combining such disparate elements. You rock the look, Trinny.

[@TrinnyLondon]

💕

[@farrukhpatel4930]

Best closet confession yet. Loved you in everything. Very inspiring. So glad you are always willing to shake it up . And your dialogue is so funny down to earth and entertaining. ❤❤

[@TrinnyLondon]

💕

[@debbie444]

Best closet confession for some time! Well done !

[@isola-bella]

"Not that I might even do anything more than have a dinner but I just want to have a good foot (or a good food) said Trinny while exfoliating the skin on top of her left foot... you killed me with this ❤! 😂😂😂

[@anitahirst3261]

I hate hate hate trainers with dresses etc and hate chunky platform boots so seeing you in elegant heels is such a treat ❤

[@kierremccune5901]

I agree with you 500%! I don't get Tinny's obsession with wearing big bricks in her feet. They're appropriate for some outfits, but she pairs them with everything.

[@nicolelela7423]

That short dress is so you. Definitely keep. Do NOT listen to the girls. It looks perfect with the first and the second jacket. It’s a KEEP!! My favorite outfit of the entire grouping!!!

[@allgoodwithme3290]

Exactly!!!

[@mareesimonis7656]

The shoes add real va va voom power! All the outfits were sexy & elegant. One exception being the super short bloomer dress .. too short. The last black/gold duo were stunning!

[@teresacarle294]

😊Actually thought it looked ✨️sensational✨️on her AFTER she removed that short bubble hem. It lengthened it & obliterated the cloying sweetness of it. She does have spectacular long, slim limbs〰️why not showcase them in her special selection of glamour heels!? 🖤Loved it paired w/the long duster coat🥂. Hope she keeps it. 💚Bridget from Cali☘️ (using my pal's YT acct)

[@audreymadden5426]

U always been stunning woman... What I like about u most is that your very honest and open when comes to styling and aesthetics ❤

[@TrinnyLondon]

💕

[@catherineofsweden905]

Trinny is just…honestly…the most inspiring beautiful woman, I can’t 😂 . National treasure.

[@ellekeogh6881]

The pearls confession! 😂😂😂 You’re so fab Trinny! Love the celine pant, legs look great!

[@alpaca2376]

Jesus Christ the commentary is as legendary as the outfits; where the outfits are elaborate chess moves designed to enhance and create subtlety based on occasions. The date better be impressed 🎉

[@EsteeWalts]

JC forgotten. It's ALL about looks and making ( wrong) impressions. 🤣 She stumbled twice on these heels. Everybody does.

[@erica6825]

Loved everything, except that super-short black dress that Lila has claimed. I thought it kind of "rubbed you out", as if you weren't your complete self in it. Absolute favourites were the navy outfit in the beginning with the pearls with a story :) and the final gold leather dress. Gorgeous!

[@KateMeacock]

Ohhh Trinny!.....Pleeeeaaaase keep your characterful, funky, cool flats......Use for walking to certain date venues, pop in your bag and swop for your gorgeous heels upon arrival! Perfect!!😊❤🎉

[@zeldabaker1331]

Love the black leather thingy, a classic piece, and liked the jacket over it.

[@thefallencure]

Omg I think I squeaked when I saw the James Lakeland! What a gorgeous piece.

[@louisejohnson5184]

I think that your feet will be screaming at you for more comfortable shoes 😮 I love your platform boots and trainers. 😂

[@notaclue822]

I do too but Trinny can do both.

[@louisejohnson5184]

@notaclue822 Yes, I agree. I got into chunky boots and trainers by watching Trinny, but I'm useless with dainty heels.

[@latifa1020]

Thank goodness you dropped the clod hoppers and are into heels!!! Love that leather dress with the Zara belt and the Gold is an absolutely gorgeous life-changing garment...

[@juliecarlson280]

I love everything, but those two final outfits are stunning.

[@lynnpetti3817]

This was great fun, as always. You remind me to “try” to have more fun with clothes. The cut leather vests were wonderful.

[@sallyannflanagan8627]

I think a short link necklace would look more modern than the long pearls, love the outfit.

[@chichipotter4487]

6:17 the most stunning outfit I have ever seen you in Trinny. Absolutely breath taking. Class all the way. So darn inspiring !!! Love from Australia

[@notaclue822]

Love the Fenwick s number. So gorgeous.

[@biancaslens]

Unpopular opinion (maybe) but I really loved you in that short dress , it was a total Kate moss moment when you added the long coat! I think you can pull it off very elegantly ♥️

[@CrazyMaryJo]

That planetary themed sleeveless architectural coat is stunning. From who/where? And is it felted wool?

[@debracannon7574]

I think the cape is Valentino x

[@CrazyMaryJo]

@@debracannon7574 did she say the fabric? Looks like a felted wool.

[@sarastarski]

That story about the Chanel Pearls! You made my day Trinny! I replayed it few times! You are a Legend! 🔥 Great video, stunning outfits and shoes 💫

[@hannahbetts5934]

GREAT title, joyous content. I completely love this. Dressing to access that side of yourself, whether or not there's a male "audience".

[@ellekeogh6881]

PLEASE DO A CLOSET CONFESSIONS ON THE JAMES LAKELAND DRESS

[@kayelle8005]

Yes. We need a closet confessions devoted to that amazing leather piece from the closing down sale!

[@tracyevans8977]

Oh my ! That leather dress in black is so Trinny . That is just absolutely beautiful

[@jmo4521]

Trinny looks absolutely fabulous!

[@margheritadefeo7433]

Loved this video! I love all your outfits! It’s true, we should let all the sides if our characters just breathe! Great advice! Love from Italy 🇮🇹 ❤

[@dorisbeckish580]

Im so jealous of you and your wardrobe. You look divine in everything you put on from the shoes to the date clothes! I loved it all!

[@mindtheprivacy]

I would have gone with the short dress. It looked amazing in her.

[@judithholder2537]

No, not mutton dressed as lamb

[@lucatri7191]

I love the black leather leaf Gilette. So awesome! A video about the different ways to wear this fancy cloth would be really inspiring. ❤

[@user-db5tb2mm9x]

Trinny, i am so happy you've got rid off all this chunkiness! All your " date" shoes look fabulous! Besides i have similar leopard print stilletos, which i totally love. I believe you should wear mini! It looks perfect on you! May be 10 sm above the knee would be perfect. Thank you for your inspiring and kind videos!

[@dons9228]

Whenever you warm up your makeup, you look so much better!

[@soniaz8874]

I know it's about being comfortable with yourself. But good lord your knees look fabulous, don't hide them! Your legs are still so youthful. For the sake of us that weren't as blessed, wear those short things in our honor!

[@elizabethrobles9934]

I’m so inspired I ❤ it. The leather at the end is my favorite. I need to try to make one.

[@daisybuckley5846]

I love how your knees have an American accent 🤣 “the quirkiness of me but not scaring off people” I’ve never related to a fashion statement more. For interviews and first dates I always have to tone down my overtly colourful, patterned and 60s/70s fashion sense. Speed dating event here in Melbourne on Easter Friday, no idea what to wear BUT I’ll make it work. Bloomers dress with long black coat is giving me Carrie Bradshaw vibes for some reason. The gold and black leather leaf dresses, OMG 😍😍😍

[@victoriapickles4110]

Heels are winners, I’m so happy you’re back in them ❤

[@kierremccune5901]

Yes! Yes! Yes! The sleek sexy shoes are sooo much better. They're feminine and accentuate your amazing figure.

[@user-px6gr8xd1v]

The lady would look absolutely stunning on a date or not ❤😘

[@mateam4024]

Wow, wow, wow!!!! Looooove all the outfits! 😊😊

[@markmasterson4811]

John Malkovich prepped for roles by getting the characters shoes right so Yr in great company Trinny.

[@leslie-anneblake6000]

LOVE the piece from Fennicks!! Absolutely gorgeous!!!great with the trousers underneath & the cropped blazer with leather cuffs❤❤❤❤

[@cdl6953]

Trinny needs to do a video on high heels - buying them, heel height, walking in them. Do you size up? Also, hacks so they don’t torture so much (make them more comfortable) as that would be a party/date killer 👠👠👠

[@janicemonroe5948]

I thought you looked exceptionally beautiful today. Love most of the outfits-and that coat w/the puff balls -so cool. Your closet is huge!

[@janet-myspinonthings7016]

I’m so appreciative of this video!

[@fabrylucy]

Loved this 🤩

[@foxyboots]

no way ................. Trinny crazy woman ! love you!!!

[@rozrena3959]

OMG the gold!!!!

[@raggiodelia]

I love closet confessions🎉Trinny you are very funny ,inspired and authentic human being.I just discover your channel short time ago.Thanks

[@beauteedit]

Love this video Trinny! Best of luck for your date xx

[@sarahtreacy7749]

Loved this! That leather black Fenwick (not sure if that’s the spelling!) dress was so versatile!! Wow!

[@TheBrownFaceBE]

I am a fan of the mini dress with the long jacket!! To me there was a sense of youthfulness and playfulness but still mature. I love my legs so I would definitely rock it. That leather piece is STUNNING! The gold… CHEF’S KISS, That would be my favorite look. The suit in the beginning would be third.

[@tinajoneswilliams4253]

I couldn't be more excited for this shift in shoes. I love them all. Xoxo 💕

[@gayane_igityan]

I need more of these confessions. You look stunning in everything…. And yes to the pointy boot

[@sarahq7569]

I come back to Trinny to remind myself how to nail the feminine look. Thank u!

[@TraceyBarracloughInspiration]

You’re a sexy minx Trinny. I wouldn’t feel sexy in heels though, because I wouldn’t be able to ruddy walk 😂 Sexiness, as I’m always saying, is a state of mind - think sexy thoughts and guess what! We can also date ourselves. Love the JL gold item; I’ve got a couple of JL investment pieces that are now probably vintage and I still wear to death, and a couple of quirky Joanne Hynes pieces. The woman I am today is edgy and cool. I hope. Thank you as always. Happy dating! 💋

[@teresacarle294]

😊Yes, Trinny's such a vibrant woman🎉. 🤫While it's not entirely my thing, I'm enjoying her exploration of sexy. I fully embrace your notion of dating ourselves. ⚡️Amping up the quality of our dress. Increase drama & glamour🎭 in our wardrobe bcos we've decided we're worth the extra effort😁. For me it's not doing it to impress anyone.🙃Although I hope it attracts lively, interesting people. Like the notion of modern 🎬Matrix😎〰️my idea of being powerful & dangerous requires walkabilty.💥Kick azz operators aren't mincing about on stilettos👠 (unless there's 🚖door-to-door car service). 😬Plus 1.5yr later, I'm still in PT mode after 2 surgeries on a broken leg & awaiting a 3rd op👨‍⚕️. 🕊Praise God, the worst of the swelling has receded on my tibia plateau fracture & my sprained ankle has FINALLY recovered. Building up strength & stability remains a priority.🤭Flats are in my foreseeable future. 🤔Lean modern minimalist, classic chic w/a decided feminine twist. Generally, prefer skirts for all that (& our extreme Mediterranean/Desert pocket 🏜). Full length trousers & blazers go off the table as soon as things hot up here🌡. 🆒️Cali Coastal streetwear. Much of my decisions are climate driven. Love 🪖camo for it's palette & parachute lightness. Utility & moisture wicking fabrics are world🌐 changing here, so I find myself leaning slightly into tech/combat aesthetic🥵. No chinos or jeans👖(except cut-offs for hiking neighborhood🏘).✂️Considering converting khaki cargo pants & shorts to a maxi skirt & bucket hat respectively. 🥰Adore living vicariously through Trinny. Tempted by her elevated pinstripe mafia style. Wanna embrace my collection of blazers w/epaulets & military🎖detail too. Inject some frivolity & funk into my trouser suits w/o going overboard. 🤓Been evaluating ways to reinvigorate ♻️ my beloved pencil & a-line suit skirts too. Find real ways to work 'em in rotation🔄. They need some🤏 friction too.😖Can't bear anything costumey🧚‍♀️. To avoid that it needs to be authentic. 🔑Need the right ⚖️balance of ♂️|♀️ energy. Cheers🥂! 💚Bridget from Cali☘️ (using my pal's YT acct)

[@ElizabethYerolemides]

Trinny how conservative can you get ! - I am shocked at how you change your style to go on a date! You have inspired me over the years to go with whatever your style is - be it over the top or whatever! The most daring outfit was the mini dress

[@ceejae2349]

Love that leather vest! It's td4 (I'm old)

[@nicolelela7423]

The navy coat with stars….everything.

[@sarahmurphy-nf4yl]

BEST video for ages 👍 👌 Really enjoyed it 🙏 🤲

[@kelleeturner4324]

This is a great one!

[@qwert3879]

The last gold leave dress is epic 🤩🤩🤩🤩🤩

[@melissalees2631]

Love this last outfit! ❤️

[@emmag2006]

Triuny looking absolutely stunning in all of those outfits. So happy to see the big clumpy shoes finally being cast aside 😊

[@rebeccaakam7466]

I’m thinking you look gorgeous in everything…You Rock it! But please don’t get rid of the chunky trainers and black boots… I love that look! X

[@EsteeWalts]

Indeed boots for soldiers or worse....orthopedic. In no way elegant.

[@eleanoretutwiler7010]

Love doing the confessions and prep for femininity! Hope you do additional color palettes as well. This was perfect.

[@dawnmon89]

Love the content! But why get rid of the black boots they are gorgeous and can be sexy :) can anyone please tell me where there are from? Have been looking for ages for ones like those thanks ❤️

[@annsandlund8376]

Trinny, you crack me up 😂apart from your expertise in what to wear and how ❤️

[@Bsowow]

love the bath robe the most 🎉

[@susantaylor5068]

Best Closet Confessions this year Trinny - you looked fabulous in all your outfits - and perfect make up every time 😊

[@leahcardzansi3924]

Stunning beautifully done the black and gold divine 😊

[@imamorninglory]

Omg! Trinnie you are so Funny! I Adore You! Best Closet Confession Yet! The Conversation is Everything! Hope You Enjoy Your Dates, You’re Looking Fabulous! Hugs Trinn!

[@ritarivera8279]

Yay Trinny , stepping up your show game … I LOVE IT … you haven’t aged one bit !!! Rick it !!

[@ritarivera8279]

Your date is lucky to have you !

[@annMarieL11]

I love this woman 😍

[@fuenmonzo]

Trinny, te sigo desde España, me encanta como combinas todo y tu frescura. I love the way you create your looks always thinking out of the box. You are awesome.

[@Emma-kb1qw]

WoW !! The last two outfits 💞✨👋

[@marycoffey9441]

Love Mollys, honesty ....... I'm not sure about the sleeves on the Michelle Vanderham dress ,a bit short and tight .

[@grainnedelaney993]

Don't throw those runners and boots away, you will be back in them, the heels make us so tired,

[@janparr6889]

she's not actually getting rid of them

[@krismyers4940]

Beautiful! Beautiful!

[@susanwilcox1783]

I love the bobble coat!

[@cattfuller]

Last gold&black outfit is good to add a splash of color though, like red clutch, emerald green, royal blue in different textures such as suede. You look amazing.

[@agnev111]

‘It's like candy I can feel it when you walk…’🍬 I was wishing it would’ve been me trying on the tights, dresses and heels mmm

[@MYKEYCARD]

Absolutely Wonderful 🙏💜🌍💜🙏

[@donnashort9634]

That leather thing!!!❤❤❤❤

[@deborahmatthews7940]

Love vlogs but I don’t think women of our age need to ask very young teenage / early 20s girls on how we should dress. Short skirts for all ages. You was rocking it until she said no. I’d sooner you consult with women same age. You are the queen of style. x

[@katarzynaflorczak990]

Great looks, especially gold :D

[@pa26mk]

I think a black choker or something around neck would make the gold outfit at the end even better. I'm a guy, so what do I know but I feel quite strongly about this, in terms of balance and just bringing that bit of black up the body to break up all the gold and match the other black accents that are going on further down. I thought you looked amazing in the shorter skirts, I didn't think you looked like mutton at all, you look after yourself and have the confidence, grace and style to pull it off. Hope the date goes well!

[@JBUHJBUH]

I've always wondered, from a guy's perspective, are there particular connotations to a choker necklace for you? If someone wore a choker on a date, would it affect your opinion of them? If so, in what way?

[@pa26mk]

@@JBUHJBUH I'm probably not the right person to ask as I don't date women, my thoughts were purely based on aesthetics here. You pose an interesting question though and im pretty curious about what men who do date women would say...

[@zabindhanji]

I absolutely love the last two dresses (blue and gold)! Now that's your kind of sexy...for the woman you are today. The bloomers were too short and 'try hard'.

[@loubella32]

Trinny, you look incredible! Enjoy the dating scene 🫶🏻

[@carolannanderson3217]

This has got to be one of my favourite Closet Confessions!!! Having followed you Trinny from the 'Trinny & Susannah' days not only have you brought me joy but helped me to love my style and what works for me. So seeing you do that for yourself at another junction in your life was very uplifting ❤. Loving the heels, you have always looked fab but 60! You are killing it...Happy Birthday xx.

[@FAQ_Qureshi]

Please do an in depth video on how to style different types of boots , loafers and sneakers.

[@queencrimsonqueencrimson]

Does anyone know where the black platforms boots at the beginning are from please?

[@salyol7]

Looking really good

[@human_no847]

Trinny who is the green abstract painting by that's in the background? It's beautiful. You looked stunning in the black skirt outfit, that was my fave. :)

[@karenfurreedan5815]

Great video Trinny, would love your advice on how to break in new shoes, particularly heels and how to walk with confidence

[@debblackmore7460]

❤❤ good luck with date love this jacket whole outfit is absolutely stunning ❤❤