How to have ageless style in menswear
How to have ageless style in menswear

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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. Given that in former times, women did not have their own money their clothes depended on what their husbands/father approved to buy and/or 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.

Menswear is 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
older woman in posh menswear summer outfit for work
Oliveo 3/4 sleeve chambray shirt with J. Crew seersucker pants, croc imprinted belt with tiger eye buckle, LV bucket bag, Tissot stone watch, Ray Ban sunglasses, Aigner sandals, and cat scarf (all own)

Secrets to ageless chic in menswear

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

  • No 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 over 40.
  • 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.
female blogger in seersucker with men's shirt for a posh casual menswear inspired summer work outfit
Side view of Oliveo 3/4 sleeve chambray shirt with J. Crew seersucker pants, croc imprinted belt with tiger eye buckle, Tissot stone watch, LV bucket bag, Ray Ban sunglasses, Aigner sandals, and cat scarf (all own)

Menswear pieces to try

Here is a list of menswear pieces you may want to try.

  • Aviator bomber jacket
  • Motorcycle jacket
  • Boyfriend blazer
  • Boyfriend jeans
  • Tuxedo pants or jacket
  • Tie
  • Trench coat, duffel or pea-coat
  • Fedora, baseball cap
  • Slim cargo pants
  • Utility jacket
  • Seesucker blazer or pants
  • Desert boots
  • Irish or plaid blazer
  • Baseball jacket
  • Buffalo plaid jacket
  • Engineer or riding boots
  • Aviator sunglasses
  • Men’s white top tank or T-shirt as a layering piece

Great menswear outfit ideas for women in midlife

Here are some further inspirations how to style the menswear look.

style blogger wearing a cat tie, leather pencil skirt, motorcycle booties and polka dot shirt Jones New York polka dot shirt layered under V-neck silk short sleeve sweater both tucked into the Ann Taylor leather pencil skirt worn with GNW tight, Hermes enamel bangles, Hermes collier de chien bangle, and Harley Davidson booties (all own). The cat print tie pulls the outfit togetherwork 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)

midlife woman in 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.

#midlifefashion woman looking chic in a menswear summer work outfit
Other side view of Oliveo 3/4 sleeve chambray shirt with J. Crew seersucker pants, croc imprinted belt with tiger eye buckle, Hermes collier de chien bangle, LV bucket bag, Ray Ban sunglasses, Aigner sandals, and cat scarf (all own)

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.

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Photos: G. Kramm

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