Pick 3-4 colors including neutrals that you want in your wardrobe. Choosing colors that compliment each other in a variety of combinations (aka a color palette) will make it easier for you to put together outfits without thinking too much.
Every guy should have...
**2-3 undershirts (crew neck AND high V), white, gray and black
**1 pair of dark denim
**1 dressy casual pair of chinos in gray or navy blue
**1 perfectly fitted suit in gray or navy (save the black for the groomsmen)
Donate or tailor shirts and pants that don't fit. Eliminate clothes that have stains or holes unless you want to communicate that you just don't care about your impact on this world. -Disclaimer: As your stylist I'm an advocate for designer holes, but only when paired with more dressy items like a suit jacket or structured sweater.
Fit is everything!Like dating it either fits or it doesn't. The same applies to your clothes. Don't force an item into your closet if it's 'almost' the right size. If you love it enough get it tailored, take in the hem or order custom, but NEVER settle for less! -Disclaimer: the "order custom" or "take in the hem" doesn't apply to your dating life;)
Check out my Pinterest board of fit tip guides: https://www.pinterest.com/tweakedstyle/men-fit-tips/
Because you strive to be a winner some of the best ways to stand out from the rest is by adding those unique style tweaks to your wardrobe and personal brand (aka the way you communicate yourself to others).
No-brainer ways to add personality to your wardrobe...
Add 2-3 patterns within your color palette that you love (Pattern guides below) Pattern Guide Here Nine Patterns Every Guy Should Know
Choose shoes that inspire you. Don't play it too safe with your shoes. Pick shoes that show your personality. I'm all about breaking the rules with style, but shoes can really make our break an outfit. Make sure your shoes are clean, no holes, stains and are not too loud for your outfit.
Accessorize! Add a sporty watch (tech chic is definitely in right now) or leather bracelet to show your down-to-earth personality.
Be prepared for everything and layer lightweight undershirts with sweaters. Throw on a medium weight jacket for colder days and you don't have to worry about being uncomfortable. Don't forget the color palette rule in Step 1. Monochromatic looks are completely acceptable this season. Just add 1-2 items that add something new (i.e. color or a pattern).