How to Dress like a Man 101

Continuing the lists to help writers mess with gendered expectations, here are the items men are told to acquire in order to fit in. Yes, this came from a compilation of such lists for men and by men in 2021. You can use this idea to mess with the stereotypes though, add items from this and the list for women to bring ambiguity or a sense of non-conformity to your narrators. ow

Clothes speak of personality, profession, and class not just gender (my take). The various articles found online from Men’s magazines promoted the higher end clean businessman look but with some searching I found the Rugged Male wardrobe within other blogs. In all, they spoke of the following items regardless of what kind of demographic they aimed for. 

  • Jeans (relaxed fit, boot fit)
  • Cargo pants
  • Carrhardts
  • Khakis 
  • Chinos
  • Suits (wide shoulder, fitting, dark colours, 2 pieces, medium weight)
  • Shorts
  • Shirts (button down, long sleeve, short sleeve)
  • Flannel shirts (plaids and checks) 
  • Sweaters (cashemere, wool, fleece, heavy, chunky knits)
  • Hoodies
  • Cardigan
  • Sleeveless shirt (but only one)
  • White tee shirts/undershirts
  • Coloured short sleeve tee shirts
  • Long-sleeve tee shirts 
  • Polo shirts 
  • Blazer
  • One long, heavy wool winter coat.
  • One long, lighter raincoat/trench coat.
  • Raincoat
  • Peacoat (long or medium length)  
  • Blazer 
  • Vest (winter weight)
  • Jackets (leather, sports, rain, denim)
  • Sport shoes (sneakers)
  • Boots (sturdy, leather, cowboy, steel-capped boots)
  • Sport shoes (sneakers)
  • Business shoes (one pair of dress shoes)
  • Flip flops 
  • Bathrobe
  • Swim trunks (not speedos)
  • Underpants, boxers, briefs
  • Waistcoat
  • Socks (sensible, plain, funny)


  • Watch
  • Rings
  • Hat
  • Sunglasses
  • Umbrella
  • Scarf
  • Glasses
  • Wallets and Money Clips (sensible, leather)
  • Gloves (leather)
  • Caps, beanies, cowboy hats, baseball caps
  • Belts (leather)
  • Cuff links
  • Ties (medium width, sensible, one red, and for fun a bow tie)
  • Storm cuffs
  • Snug-fitting collars 
  • flap pockets 
  • Scarves ( matched with the proper clothing) 
  • Thicker material, heaver stich, longer inseam, buttons on right side, straight cut.

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