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4 months ago, I posted a thread on MFA asking for fashion tips for big guys. Someone told me to come back after losing weight. Challenge Completed: I’m down 65 pounds (and counting) in 4 months and now all my clothes are visibly baggy. Any tips for starting from nothing?(r/malefashionadvice)
Congrats! Although, for the record, “come back after you lose some weight” isn’t very common advice in MFA.
As far as starting from scratch, the Basic Wardrobe guide in the sidebar is a great start, but you’ll want to think about what works best in your climate, for your age, and for your job/school. It’s a inoffensive baseline to help you be well-dressed while you learn and develop your own style. The incredibly abbreviated version is straight/slim-leg jeans in a dark, nondristressed wash, vneck tshirts, Oxford cloth button-up shirts with button-down collar points (aka ocbds), simple canvas sneakers in neutral colors like white or gray, and brown leather shoes or boots in classic styles.
Edit: More details for a basic wardrobe on a budget. I’m going to focus on things you can try on in person, since I think that’s critical when you’re starting from scratch.
For jeans, Levi’s 501/514/508/511, which should be available at every anchor store at every mall in America. JCPenney has newly-renovated Levi’s sections in all of their stores, so that might be a good place to start. The numbers refer to different cuts (normal vs. slim legs, straight vs. tapered, etc), so I advise trying all of them on, and in a couple different waist sizes. If you’re unsure about which fits you best, post a thread on MFA with some fitting room pics. We’ll help you out.
Mossimo v-neck tshirts at Target are usually $8-10 and fit most people really well. Almost everything they have is a versatile color, but for wearing with dark jeans, I’d avoid navy and black because they don’t create enough visual distinction. For a quick fit check, make sure the shoulder seams of the shirt line up with the bony protusions at the edge of your shoulders. Too many people wear shirts with shoulder seams drooping halfway to their biceps, which looks sloppy.
Target’s Merona ocbds are also a decent choice, although this is a common enough shirt that they’re going to have something very similar at JCPenney, Macys, H&M, or any store that carries a large line of men’s clothing. Look for solid white or light blue. You can use basically the same quick fit check for ocbds that you do for t-shirts.
A lot of mall stores will carry Vans Authentics, which are a classic canvas plimsoll. Some of the stores are going to be obviously targeting a teenage demographic, but you can just ignore everything but the shoes you’re looking for. Look for white, off-white, or light grey. Avoid black. There’s a misconception that black sneakers go with everything, but it’s my mission to disabuse people of that idea. Black is a stark, somber color that’s incongruent with the casualness of sneakers. Black’s also not a neutral, and as I mentioned in the bullet about t-shirts, it doesn’t go well with dark blue denim.
For casual leather shoes, Sperry Top-sider boat shoes are a really popular option, but they’re more of a spring/summer shoe in my opinion, so we’re getting to the point where they won’t be in season. Some versatile options that are more appropriate for Fall are desert boots, tan bucks, and blucher mocs. Unfortunately, these may be harder to find in local stores. Again, shades of brown are what you want.
You can pick up all of this stuff for $300-400, which isn’t a bad investment for looking good.
2nd Edit: I just saw in another comment that you wear size 15 shoes, so mall stores may not work out for you after all. I put this guide to large-sized footwear together a few weeks ago, and you can see that most of the shoes I recommended above are available online in your size.