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Menswear inspired clothes have always inspired women. Think Marlene Dietrich in her tuxedo in the 30s. Babyboomer may recall how we fought to wear jeans and/or pants at school. Remember the power suits with camisoles underneath in Europe in the 80s. Read how to get ageless style in menswear without looking like trying too hard or not trying at all.

  1. Menswear Is Related to Power
  2. Is Menswear a Risky Trend to Style Effortlessly Chic
  3. Stylist’s Secrets to Ageless Style in Menswear
  4. Great Menswear Outfit Ideas for Women of All Ages
  5. Try a Tie as Twist on the Menswear Trend
  6. Top of the World Style Linkup Party No. 308


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Menswear Is Related to Power

Ever since mankind developed clothes, those who had less power or wealth admired and desired the clothes of the upper class. This means the clothes of those in power. When the commoner started to wear similar garmentents those in power created sumptuary laws to prohibit wearing luxe.

Given that in former times, women did not have their own money, what women wore depended on what their husbands’/father’s approval and/or what these men bought for them. Once women got into the workforce, they started wearing men’s clothes for practical reasons, but also to show their new gained independence/power.

Menswear was born.

Is Menswear a Risky Trend to Style Effortlessly Chic

Menswear can become costume fast when styling it like Carrie Bradshaw on Sex and the City. The same applies for the corset under a menswear suit. After a certain age, this Angelina Jolie inspired evening outfit looks like trying to hard and/or plain ridiculous. Well do I have to mention the men’s suit with the jacket worn backwards?

Wearing a non-tailored men’s suits with flat oxfords and a tie looks like not trying at all.

Instead go for one piece at a time, and not head to toe. It’s an everyday outfit not shopping your closet for a Halloween look...

Wear menswear with a feminine touch. #styleadvice Click To Tweet


American West style outfit with suede blazer jeans shirt

style influencer in menswear inspired suede blazer, jeans and tee outfit with sunglasses
Orvis suede blazer, Chicos Tee, amethyst buckle, Dooney & Brouke top handle snake print bag, London Jean boyfriend white denim pants, Tayler’s Gold’n Stone earrings, Prada pumps, Chicos top, Eagle Eyes sunglasses, topas head band


Stylist’s Secrets to Ageless Style in Menswear

To look ageless in menswear at any age stick to the following:

  • Never wear menswear all over.
  • Female ascents are a Must.
  • Go for pants suits with classic lines with jackets that are nipped in at the waist. Better even, unmatch the suit.
  • When wearing full-leg pants, treat them like a long skirt and showcase your waist.
  • When you wear boyfriend jeans go for a straight, not too tight leg and a relaxed style. Tuck in you top and/or wear it with a blazer for a chic polished look.
  • Look for cargo pants that are cut slim enough that you still can showcase your waist.
  • Shirts with French cuffs are a no failure menswear item that looks great with a skirt or jeans.
  • Oxfords with heels or brogues in silver, gold or gem colors are chic menswear items for women of all age.
  • Tuxedo-inspired jackets are great with jeans.
  • A tuxedo suit is great for a black tie event when worn with a camisole, pearls and patent leather pumps. Marlene Dietrich is the big style icon for the look.
  • Leather Bermuda shorts look stylish with sheer black panty hose or black tights in winter. More on styling leather shorts in the guide at the link.


#midlifefashion woman looking chic in a menswear summer work outfit

older woman in posh menswear summer outfit for work

female blogger in seersucker with men's shirt for a posh casual menswear inspired summer work outfit
Outfit details: Oliveo 3/4 sleeve chambray shirt with J. Crew seersucker pants, croc imprinted belt with tiger eye buckle, Hermes collier de chien bangle, Tissot stone watch, LV bucket bag, Ray Ban sunglasses, Aigner sandals, and cat scarf



Menswear Pieces to Try

Here is a list of menswear pieces you may want to try. Links go to guides on how to style the respective items. Which ever pieces you pick, pair them with feminine pieces for a nice tention.

  • Bomber jacket
  • Motorcycle jacket
  • American West men’s suede blazer
  • Boyfriend blazer
  • Boyfriend jeans
  • Tie
  • Trench coat, parka, duffel coat, janker or pea-coat
  • Tuxedo pants or jacket
  • Fedora, baseball cap, driver’s cap, fisherman hat
  • Slim cargo pants
  • Utility jacket
  • Seesucker blazer or pants
  • Irish or plaid blazer
  • Baseball jacket
  • Oxfords, lace-up shoes, boat shoes, loafers
  • Buffalo plaid shirt or jacket
  • Desert or combat boots
  • Engineer or riding boots
  • Aviator sunglasses
  • Men’s white top tank or T-shirt as a layering piece



Great Menswear Outfit Ideas for Women of All Ages

Here are further inspirations how to style the menswear look.

work outfit with Irish blazer with leather sheath dress Leather sheath with Orvis Irish blazer, layering top, GNW tight, Clarks booties, booties (all own), and boot toppers c/o Top of the Boot

over 50 years old woman in menswear inspired outfit with blazer for work Orvis menswear inspired Irish blazer over GNW Luxe sweater with Oscar de la Renta leopard print scarf, INC leather pants and Clarks booties (all own)

fashion blogger in unmatched suit of plaid blazer and pants GNW Luxe cashmere sweater with Burberry menswear inspired plaid blazer, Hermes collier de chien bangle, Clarks booties, statement necklace, and chocolate INC leather pants (all own)

stylist in menswear seersucker pants and gingham button-down shirt Menswear inspired J. Crew seersucker cropped pants, Carhartt gingham button-down shirt, Kieselstein Cord belt and buckle, Hermes collier de chien bangle,  Juicy Couture slides, Longchamp cuir pliage bag, and Ray Ban sunglasses (all own)

ageless style in menswear with boyfriend jeans with navy blazer, plaid shirt, and pumpsLondon Jean white denim boyfriend jeans with Oliveo plaid shirt, Oliveo navy blazer, L.K. Bennett pumps, Ray Ban sunglasses, Kieselstein Cord belt and buckle, and structured bag (all own)

If you liked any of these outfit inspirations, it would help me if you pinned them to your own Pinterest board. It’s a great way that your friends, family, and others can see them too.

Stylist tip: Don’t wear menswear from head-to-toe.



Try a Tie as Twist on the Menswear Trend

In one of these menswear cycles, I bought this cat tie for me a couple of years ago. This outfit is a twist on the menswear trend. A little bit classic with a polka dot black and white button down shirt, which is two classics in one: Polka dots, and the eternal black and white trend, which is also a perennial trend. Polka dots are very feminine and posh when they are small – read not larger than the nail of your pinkie in size.


influencer wearing a Windsor knot tie, leather skirt, shirt, vest

stylist in menswear tie
Layering a silk short-sleeve sweater over a Jones New York polka dot shirt worn with tie, Ann Taylor leather pencil skirt, GNW tights, Harley Davidson booties, August Silk top, and accessorized with Hermes bangles and a collier de chien belt (all own) for a posh menswear inspired work outfit


The cherry red of the tie and the black, gray and white cats have a gender neutral to feminine vibe. Red is a very feminine color. The skirt being made of leather, the motorcycle booties and studded belt give the outfit an edge. The bunch of red bangles add to the feminine touch. I love the Windsor knot because it is so big.


When wearing the menswear trend go for a mix of very feminine items with the menswear. #agelessstyle Click To Tweet

Do you like menswear? How do you style your menswear items? What are your greatest concerns when styling your menswear items? Let me know, I am curious.

When you liked the outfit recipes of this post, and want recipes for all kind of dressing situation in midlife, buy my book How to Dress for Success in Midlife.



Top of the World Style Linkup No. 308

Top of the World Style linkup party every week on Thursday

Welcome to the Top of the World Style linkup party.


Debbie in hankerchief abstract floral print dress
Debbie from Yours Styled Story became the Top of the World OOTD Readers’ Fav for the second time in a row. Photo from her post


jacqui in gray long jacket blue sweater black leather pants and booties
Jacqui from Mumma B Stylish became the Top of the World Style winner. Photo from her post


leelo in graphic tee tulle skirt denim jacket ballet flats
Leelo from Beauty by Miss L. became Top of the World OOTD My Fav. Photo from her post


Congrats Ladies! Grab your award buttons.

See these awesome looks at the Top of the World Style #linkup party. #timelessstyle Click To Tweet


To the party


I invite all fashion and style bloggers to co-host the top of the World Style linkup party. Just send me an email with your request.

Photos: G. Kramm

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