Timeless Dressing

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Updating the classics.

After our day together in New York City I was really taken to the idea of wearing a timepiece and started thinking about how that could integrate into my daily wardrobe from working days to all the holiday parties coming up. I was talking to my friend Laurel about this, who herself has such amazing taste (remember THIS shoot?!), on updating timeless dressing. I loved the idea of wearing a watch; it says a lot about a person, and with the IWC Portofino Midsize I think that says someone who is classic, intelligent, and above all timeless.

But let’s look at timeless dressing.

Laurel and I discussed how to make it more interesting, how to update the standard little black dress, how to do something surprising with a wide leg trouser… so in a sun filled studio on Manhattan’s west side we played dress up with Jessica Wall, with our city shining bright in the background, and spent together that thing that is the most valuable of all: time.

Cover image~ IWC Portofino Midsize Ardoise & Diamond Timepiece


The best thing to wear with black lace is more black lace. 

Above~ Jacket by TOME | Lace Playsuit by L’Agent by Agent Provocateur  | Skirt by TOME | IWC Portofino Midsize Ardoise & Diamond Timepiece


A full, dramatic skirt is essential for evening dressing, especially when worn with a backless silk shell. 

Above & Below~ Cream Silk Top by Chadwick Bell | Skirt by Marc by Marc Jacobs, Shopbop.com | Mary Jane Hells by Manolo BlahnikIWC Portofino Midsize Ardoise & Diamond Timepiece


Sexy doesn’t have to mean sleeveless. A long sleeved LBD with a deep V neck is a great update on a classic.

Below~ Dress by Donna KaranIWC Portofino Midsize Ardoise & Diamond Timepiece


A side tie blouse is the chicest twist on the classic silk shirt. This shirt is both sexy and understated.

Below~ Silk Blouse by ProtagonistIWC Portofino Midsize Silver & Diamond Timepiece


There’s nothing yummier in the world than satin and cashmere. This combination makes me feel like a baby bunny. 

Below~ Dress by Nili Lotan, Shopbop.com | Sweater by Protagonist |

 IWC Portofino Midsize Automatic Moon Phase Mother-of-Pearl & Diamond Timepiece

IWC_Timessless_Dressing_08   IWC_Timessless_Dressing_12

Every woman needs a great pair of wide leg trousers. Give this classic an update in a graphic print.

Below~ Polka Dot Trousers by Ralph Lauren | Turtleneck by Ralph LaurenIWC Portofino Midsize Silver & Diamond Timepiece

IWC_Timessless_Dressing_13 IWC_Timessless_Dressing_14

Nothing is more timeless than a trench coat. Styled in to an all white look, this piece is always stunning. 

Below~ Trench by Protagonist | Trousers by Ralph Lauren | Top by Brunello Cucinelli | Iriza Kitten Hells by Christian Louboutin | IWC Portofino Midsize Silver & Diamond Timepiece

IWC_Timessless_Dressing_15 IWC_Timessless_Dressing_16

Below~ Jacket by TOME | IWC Portofino Midsize Ardoise & Diamond Timepiece


A structured, oversize sweater is the perfect counterpoint to a sheer skirt – especially in black and white. Worn with loafers, the look stays classic and cool. 

Below~ Cream Sweater by Chadwick Bell | Embellished Skirt by Donna Karan | Loafers by Rupert Sanderson, Shoescribe.com | IWC Portofino Midsize Ardoise & Diamond Timepiece

IWC_Timessless_Dressing_20  IWC_Timessless_Dressing_37


Never underestimate the power of a little white dress. 

Below~ Dress by Marc Jacobs |  IWC Portofino Midsize Automatic Mother-of-Pearl & Diamond Timepiece


A classic cardigan goes mega sexy when worn with a perfect black lace bra. 

Below~ Cardigan by Giulietta | Lace Bra by L’Agent by Agent Provocateur | Burgundy & Cream Skirt by GiuliettaIWC Portofino Midsize Automatic Moon Phase Mother-of-Pearl & Diamond Timepiece



An oversize sweater with a flowy dress is the epitome of classic American dressing.

Below~ Sweater by Michael Kors | Dress by Wes Gordon | Burgundy Booties by Tabitha Simmons, Shoescribe.com | IWC Portofino Midsize Silver & Diamond Timepiece

IWC_Timessless_Dressing_26 IWC_Timessless_Dressing_27 IWC_Timessless_Dressing_28

The classic power suit gets an update with wide leg trousers and a men’s inspired tie belt. 

Below~ Blazer by Alexander Wang, MatchesFashion.com | Trouser by Balenciaga, Matchesfashion.com |  IWC Portofino Midsize Automatic Mother-of-Pearl & Diamond Timepiece

  IWC_Timessless_Dressing_33  IWC_Timessless_Dressing_35

PS~ IWC & me

All watches from IWC’s Portofino Midsize Collection | Modeled by Jessica Wall of Ford Models | Styled by Laurel Pantin | Makeup by Christine Cherbonnier | Hair by Michael Thomas Lollo | Shot at Jack Studios in NYC

  • Nice to finally see that result of these as I had seen you post about it on instagram. Lovely pictures.

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  • I am head over heels in love with every. single. look. Absolute perfection, class and sophistication without going overboard, I’m swooning!

    And the light in that studio is so so so beautiful! Amazing shots Jamie (the cover photo and fifth photo from the bottom are my absolute favorites!!).

  • Justine


  • Love the photos and the natural lighting. So beautiful (as always)!

  • Jamie

    The posing. The lighting. You nailed it. Phenom. Mmm hmm.

  • sam

    pretty face and fashion sense. Idol! Blessing that SATCH here in Australia is at 60% discount on garments ( http://www.satch.com.au/sale/) I will imitate all you have posted here! haha

  • pablohc

    Jamie, your use of black and white for contrast is absolutely marvelous! I admire your work so much!

  • Naomi

    That’s pretty rad. I love the sensibility in your picture taking!


  • Yvaine

    Eveything on this site is just like-able! They are what I patterned and what I shopped for today from Bell&Barnett…By the way, let me share that Bell&Barnett is having closing down sale.Check this out: