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I recently got promoted and, as an overweight guy, I find it difficult to get clothes that look fashionable and make me feel good wearing them. This is what I wear today. Advises?(r/malefashionadvice)
Firstly, I commend you on seeking critique. It shows you care about how you wish to present and carry yourself, and how you wish to be perceived by others. That said, what is mentioned below is truly meant to be constructive and not destructive. Please don’t be offended by what I have to say.
- As previously echoed, the collar of your shirt is a disaster. At a minimum, I definitely recommend some collar bones/stays. Preferably in metal like stainless steel, silver, or brass. They add weight to your points and prolong their shape. These are awesome in an “emergency”. In future, I recommend carefully ironing your collars to keep them in tact and in form. Bonus points for spray starching your collars too. This can be accomplished when ironing. (If you don’t do ironing, plan to only dry clean your shirts and replace much more frequently.) More on shirts later.
- Jacket is okay, but far from phenomenal. It is an approachable style and functional, however it could fit you much better. You should aim to add a few properly fitted jackets/suits to your wardrobe. These should include a couple of investment pieces. Seek out a local tailor that you trust, or a retailer that includes tailoring with their own on-staff tailor. (Please stay away from 5 for 1 deals.) As for colours: Charcoal and/or Elephant Grey, Navy, and lastly, if you must, Black. Also, with your skin tone (or so it appears from the photo), you could also successfully pull of some rich browns. Perhaps Espresso or Chocolate. Some additional tips: Avoid fused jackets like the plague, and opt for side vents in the rear for your body-type. Also, always, always have your jacket buttoned unless sitting down.
- Trousers/Pants. Donate those baggy Khaki-looking pants. Pick up some properly fitting trousers for when you don’t wear a suit. Black, Charcoal etc. They will flatter you much better providing you with a proper and sleeker silhouette.
- Shoes. Those in the picture may be functional but they don’t do anything else for you. Aim a little higher and classier. These should be another investment as your feet have most-likely stopped growing and you appear mature enough to care for them properly. I do like brogues, and wing tips (as mentioned by others) but simple and elegant lace ups will do much, much more for you than your current pair and will be more multi-functional. Black lace-ups first, then add some brown shoes. Perhaps brown brogue or wingtips. FYI… Never grey. Ever.
- Belt. Choose a nice high quality reversible belt (Black/Brown) with a nicely understated and removable buckle. Pay close attention to the quality and finish of the buckle build. The aim is that the belt is to be replaced over time, but the buckle should be timeless. Here’s one that is stylish but not overly flash. Casual belts are way too easy to come across, and almost any will do.
- Shirts. White shirts are a staple. Find a style that you are comfortable with and that fits you well. Then buy a bunch. Then experiment with colours and patterns and fabrics. Branch out from just Oxfords, with other fabrics. See here for a nice and helpful guide. Tip: Store a few shirts at work in a closet or folded neatly in a drawer. You never know when a refreshed change of shirt will save/aid you.
I truly hope this helps. I look forward to seeing some new pieces/outfits in your wardrobe.
All the best good Sir.