Reddit mentions of Timberland Men's EK Brook Park Chukka Boot,Brown Smooth,7 M US

Preface: This is going to be a long post, but I like oversharing/giving details.

I've only started to GAF about how I look/what I wear this year, it's been a very "informative" process. Wish I would've done this 10 years ago, but c'est la vie

 

I'm short + overweight (working on that though! Have a personal trainer, down 20lbs so far, still a ways to go, but progress is being made!) so any type of style has always been a struggle. EVERYTHING needs to be altered, especailly pants. I work in IT, dress code is business casual (most days its pants/shirt, occasionally jeans/polo, etc), although I've always trended closer to the business side of business casual.

In the past, I always went through a Harbaugh-inspired routine of having a set standard template that didn't require much thought: of Black Pants (Eddie Bauer), Black Socks, Black Belt, Black Shoes, and then just "mix it up" with different shirts (CT Non-Irons). My main concern was to avoid any type of faux-pas, better to play it safe and consistent.

 

Frustrated at myself, kinda hitting a midlife crisis this past winter, I decided to revamp everything. Reading a ton on MFA, GQ, MensXP, AoM, etc, got a crapload of conflicting info, and decided just to dive into it - I've tried to develop some sort of sense of style, I do know that I prefer quality/classics over trendy, and I thought the "good" brands would help me stick out some. Clothes, Shoes, Watches --> tried to improve it all.

 

This is what my "Wardrobe" now consists of, 90% is less than year old. any gaps/comments would be appreciated - Plus, as I lose weight, it's giving me opportunities to get new clothes, so always looking for new things. I'd proably like to have fewer but BETTER clothes, if I could do it over again.

• 30ish Dress Shirts, mostly all from CT. Some of them are getting too baggy, so will probably thin the heard by 10 or so in the next week, and replace them with 5 smaller cut shirts.
  
  
• 12 Polos, 5ish are various athletic/sports related ones, the rest (newest ones) are Lacoste, Polo, and Brooks Brothers
  
  
• Shoes: Cole Haan Lenox Hill Cap Toe Oxford, Black , AE Oak Street Cap-Toe Oxford, Black , Cole Haan Jay Grand Cap Toe Oxford, British Tan , AE Neumok 2 Wingtip Oxford , AE Park Avenue Cap-Toe Oxford, Black --> Reserved for formal occasions only , Nike Killshot 2s , Adidas Originals Superstars , Timberland Brook Park Chukka Boot, Brown Smooth , Sperry Top-Sider Gold Two-Eye Boat Shoe, Congac , [GH Bass Proctor Oxfords, Tan] (https://www.ghbass.com/product/proctor+buc.do)
  
   
  
  Pants:
  Normal rotation of 3 Blacks, 3, Navys, 2 Dark Gray, 2 light gray - All with the legs shortened + tapered, I don't get too radical with the pants.
  
   
  
  Other stuff:
  
  
• A bunch of "fun" dress socks
  
  
• Now have a collection of Watches: Bulova Curv 98A158, Gray , Michael Kors Gareth Brown, Citizen Ecosphere, Black/Blue, Skagen Titanium Mesh, Seiko Solar SSC139, Gunmetal/Silver, Seiko Solar SSC446, Silver/Gold/Black
  
   
  
  Summary: I don't know what this all adds up to, what "Style" this is, but I have to be honest, I do feel a lot better regarding the TYPES of clothes that I wear, and I have gotten a number of compliments, each one that I cherished greatly ;)
  
   
  
  TL;DR : I read too much stuff online, got confused, bought a ton of random stuff, and don't have any more space for new clothes. I do feel a little better though