Next investment on a 400 USD budget. live in CT and NYC

[hb20091]

Hello All. A Merry Christmas and a Happy new year in advance to those who may respond to this post later.
So Ive been lurking for over a year expanding my knowledge and understanding of what makes/breaks a wardrobe, suits and general style in particular for which Im thankful to this forum. Ill make this thread short to avoid making a novelette.
Query: Ive build up a bit of a wardrobe and seem to be in a position where I have exactly 400 USD for investing in my next item/s. The item I may be looking into may include the following and I require guidance as to what would serve me best in the long run.
1: Casual winterwear such as long sleeve henleys/sportshirts to layer into my jackets.
2: Dressier boots such as a Chukka or a Chelsea with vibram soles ( I live in Norwalk which is hilly and snowy through the winters so leather might be a no no ?). Also Id be taking some long city walks in these so Im wondering if theyre comfortable enough for that purpose
3 knit ties
4 Sport coat/s ( I already own a blue blazer but its almost 6 years old and in need of retiring . Im leaning towards designs similar to Spier and Mckay Neopolitan lapels and suitsupply havanas )
5 jackets/coat/pullovers

I need help honing in on one or two of these items since I realise that getting all of them altogether would be a challenge and just take the fun out of slowly building one .
A bit of info about me and what i own and what i mostly would be wearing these for for those who wish to require more info before commenting:
26 yo Medical Grad. Moved to Norwalk with the wife and have basically been a hermit over the past few months giving exams. The only times Ive gotten to dress up have been when we go see NYC or when were having date night and these items will mostly be used for that purpose.
My wardrobe currently includes:
1a couple of dress shirts (mostly white french cuffs) with a few gingham sport shirts and a blue OCBD (CT Uniqlo Canali and Muji)
2 Oxfords have a Barrett Black oxford which I believe is Blake stitched but does its job well. havent used it beyond formal events. 1 dark brown oxford from Fragiacamo (not Ferragamo). Its an italian shoe brand Ive only seen mentioned once here but again looks good, Blake and does its job for formal events.
3two navy suits that I got made from my country (Pakistan) . theyre fused but the measurements are good enough as is the fit. 1 charcoal Birdseye which I paid a bit for that actually has a full canvas construction(checked with a tailor here to confirm) so Im happy on the suits department.
4 A chesterfield coat from Uniqlo that surprised me in terms of how its held up so far.
5 Trousers and chinos that mostly occur in grey and tan barring a houdstooth trouser and a copper colored chino.
6 two sneakers (one white from Lacoste) and one blue slipon with white soles from COS
7 ties that are mostly solids or stripes and perhaps a bit too wide for e except a knit blue I own which is why im planning on expanding in that territory(grenadines)

Thats about it from my wardrobe.
I appreciate any and all comments .

 

[emptym]

I'd get the boots first. A chukka or a chesea in a classic style will serve you for decades if you take care of them, and you can wear them casually with jeans now or with a coat and tie later. Imo, chukkas are better than chelseas for wear w/ a sportcoat and tie. But I noticed from @dieworkwear's blog that Pediwear has the RM Williams rubber-soled craftsman on sale for about $350 after deducting VAT. Those are a great pair of boots. I suggest getting that and one or two of the smaller items on your list, like a knit tie. If you got the RM Williams, you'd have about $50 left in your budget. KJ Beckett has some good knits for about that, shipped to the US. You should be able to find one from Polo on eBay for that too. Lands End often has them for less. Kent Wang, Conrad Wu, Drakes, and others sell them for more.

 

[hb20091]

I'd get the boots first. A chukka or a chesea in a classic style will serve you for decades if you take care of them, and you can wear them casually with jeans now or with a coat and tie later. Imo, chukkas are better than chelseas for wear w/ a sportcoat and tie. But I noticed from @dieworkwear's blog that Pediwear has the RM Williams rubber-soled craftsman on sale for about $350 after deducting VAT. Those are a great pair of boots. I suggest getting that and one or two of the smaller items on your list, like a knit tie. If you got the RM Williams, you'd have about $50 left in your budget. KJ Beckett has some good knits for about that, shipped to the US. You should be able to find one from Polo on eBay for that too. Lands End often has them for less. Kent Wang, Conrad Wu, Drakes, and others sell them for more.

Appreciate the helpful response! I was gravitating towards the chelsea/chukka choice as well since I originally planned on monkstraps vs boots and boots overall just serve me better for the weather.
One little addition to the query though and Im sorry I forgot to add this earlier:
Im 5 ft 5 inch in height and Ive got a shoe size that fits a 7e Allen Edmonds PAs/Strands etc. My boot size is a complete mystery to me since ive never owned or tested boots out. For that reason alone Im thinking of trying boots out in person. Theres an Alden Factory seconds/Shoe mart collection a walk away from where I live and Ive got a few Allen Edmond stores here as well. Other than those two Im thinking of swinging by The RM store in NYC and comparing its fit with the AE and Aldens.
How would you say the quality of the Chelsea/Chukkas of AE and Alden seconds compare with that of RM williams (non cordovan)? And apparently Massdrop is doing a sale on an AE chukka as well and Im wondering how that compares as well

Also thanks for the tie referrels. Kj Beckett has some beauties in there.

 

[emptym]

Imo, Alden, AE, and RMW are about the same in quality. I like Alden's lasts and patterns better than AE, so I have a few pairs of Aldens (particularly the LHS), but no AEs. I'd think one would have to judge seconds on an individual basis. If the Massdrop AE chukka is the unlined suede ones, then they look good and are a great value imo, but not appropriate for a NY/CT winter. For that I'd go with the RMW in the link. RMWs make what many think of as the quintessential chelsea, in part because they're wholecuts and the specialty of the company.

 

[hb20091]

Imo, Alden, AE, and RMW are about the same in quality. I like Alden's lasts and patterns better than AE, so I have a few pairs of Aldens (particularly the LHS), but no AEs. I'd think one would have to judge seconds on an individual basis. If the Massdrop AE chukka is the unlined suede ones, then they look good and are a great value imo, but not appropriate for a NY/CT winter. For that I'd go with the RMW in the link. RMWs make what many think of as the quintessential chelsea, in part because they're wholecuts and the specialty of the company.

Thank you again for that. Ill be on the lookout for the same model and see what size id order on pediwear based on that. Just in case though, since i might as well try both, would you have any recommendations on who makes a good Chukka Boot in that range (under 400 USD). Im seeing some Alden, AE, Loakes, Sanders and Some Crockett and Jones and Cheany ones that barely make the mark in that budget. Or is it mostly of whichever fits me best when it comes to these?

 

[emptym]

Yeah, fit is probably most important. There are subtle styling differences in chukkas (1, 2, 3, or more lace holes, for example, or last shapes). Alfred Sargent makes a good chukka. I'd probably check riderboot.com for sales. Their RBCB1 is a longtime favorite of mine.

Your RMW size should be one less than your Brannock size, so I'm a 10 C on the Brannock device and took a 9G in RMW.

 

[AlexWilliams]

I would go with the sport coat and the boots first because these pieces are more expensive and if you have the money at the moment, just get them and after you'll little by little get the rest. I would invest in a good pair of boots because these can last you for ages if they're of good quality. You can find some good quality but not that expensive pullovers and also some knit ties on Amazon, I get a lot of clothes from there and I'm pretty satisfied. The return policy is also good, just in case you don't like something.

 

[Phileas Fogg]

I would go with the sport coat and the boots first because these pieces are more expensive and if you have the money at the moment, just get them and after you'll little by little get the rest. I would invest in a good pair of boots because these can last you for ages if they're of good quality. You can find some good quality but not that expensive pullovers and also some knit ties on Amazon, I get a lot of clothes from there and I'm pretty satisfied. The return policy is also good, just in case you don't like something.

you answered a thread nearly 3 years old. Pretty sure by now the case has been settled.

 

[mhip]

I'd go with some JMM frames, since $400 3 years ago is about $650 today...