November 07, 2012

How to dress a man

Ever since I've known my boyfriend of nearly 8 years, he has only ever had 2 opinions about his wardrobe - he doesn't have enough clothes (true) and men's fashion is so boring that he hates to shop (not true!).

The issue is not that he doesn't care or have a sense of style, he does actually, but his lack of enthusiasm and patience for shopping and his lack of desire to own a VARIETY of items rather than a few staples (that get replaced as they wear out) has left his wardrobe predictable and changing it has always been too big of a fashion mountain for me to try and climb.

This weekend however, he finally asked!  The magic question came - can you please help me shop?  Of course I can! I love going through closets, weeding stuff out, and filling in the gaps.  Although he instantly refused to let me reorganize/color code his whole closet (boooo, not sure how he ever finds stuff), I was able to sift through the rubble and had quite a good time designing my new boyfriend. Such a great tall dark and handsome canvas if I do say so myself, just needs a little decorating!

This weekend also forced me to learn what I like about male fashion (not something I usually pay much attention to) and what would be the least painful way to take him around the stores on Saturday.

I came up with a few basic rules to solve typical guy shopping problems and even wrote down a list of what he should have in his closet so we could be targeted and keep the experience relatively painless.

Here is my Saturday dissected into problem, solution, and goal.

Problem: Guy Shopping Pitfalls
  1. Shopping takes too long - usually because they don't know what they're looking for
  2. Not shopping with outfits in mind - hence the random assortment of shirts in their closets
  3. Forgetting about layering - add some life to a plain shirt with a vest or sweater
  4. Clothing that's uncomfortable - if it's not comfy, they probably won't wear it (case in point - most guys hate dress shoes)
  5. Need to have an end in sight - start the day with a good plan of attack and take little breaks to refuel.
 Solution: Fairy Girlfriend Shopping Rules
  1. Take stock of their wardrobe.  In my case, he had a random assortment of shirts, some good blazers, and 2 pairs of distressed jeans.
  2. Make them a plan of attack. Decide which stores you're visiting, what you're looking for in each one, and what order you'll be visiting them in.
  3. Be a personal shopper! Pick out lots of items and make them try things on.  Take thought out of the process and just get them in the dressing room before they realize what's happened.
  4. Keep their aesthetic in mind.  Most guys do care about "their look" and they need to feel comfortable so don't go handing him those shiny waxed jeans unless he can handle it.
  5. Be encouraging and offer opinions.  It's way more fun to shop when someone picks something out for you and loves how you look in it. I also found that by telling him the details I was looking for in items, he started to have more of an opinion himself on what he liked.
Goal: Starter wardrobe for my dude
(he works at a software company so jeans/blazer is fine for work attire)
  1. 2 pairs of jeans - one casual, one "fancy" for work (like a dark wash)
  2. 2 pairs of pants - not necessarily fancy but something that can give him more variety, like khakis (NOT cargo pants or anything with zippers)
  3. 7 nice shirts - not t-shirts.  Polos, button ups, etc
  4. 4 sweaters/vests - and the layering begins!  If he has some knits that coordinate with the nice shirts, he'll instantly up the style factor a notch
  5. 4 t-shirts - comfy, no holes! and they can't have software logos on them
  6. 2 comfy sweaters/sweatshirts with style - nice close fitting hoody or equivalent
  7. 3 pairs of shoes minimum: 
    1. Dress shoes
    2. Gym shoes
    3. Walking shoes (not to be confused with #2, running shoes need to be forbidden outside the gym)
  8. Jackets:
    1. 2 blazers
    2. 1 fall coat (leather jacket would be great or wool coat)
    3. 1 winter parka


  1. Haha I am totally in charge of dressing my man. I have to be very aware of his favorite items. He doesn't really like to switch things up much.

  2. Um you should come down and overhaul MY closet!! haha you're so organized!!!