Help me mix & match my new clothes!
September 15, 2014 9:31 AM   Subscribe

I just purchased a bunch of new clothing at Theory, which is definitely a much hipper store than I'm used to shopping at. (My old standby was Banana Republic.) The sales staff was very helpful, and I'm very pleased with what I came home with, but I'd love some help in mixing and matching everything. Photos of (almost) all of the items I bought can be found here.

I've labeled everything "shirt 1," "shirt 2," etc. since some of the color differences are pretty subtle, so if it's easier to just call out number combinations ("shirt 3 with pants 5 and sweater 1"), that would be great. The one thing missing on here is a third sweater that's the exact same style as the other two except it's a very dark navy. (I couldn't find it online and I couldn't take a picture of it that didn't make it look black.)

I also have a few specific questions:
• What color socks should I wear with these shoes? (I also got them at Theory, but they are from Common Projects, in case you are curious.)

• And speaking of shoes, any recommendations on other styles of shoes to think about that might go well with any of these outfits?

• Should I be wearing belts with these pants? They all fit quite snugly (much skinnier than I'm used to!), so I'm not sure. But if so, suggestions on belts would be great.

• I also need new jeans. Theory had some great jeans from Rag & Bone, but they were all button-fly, which is a deal-breaker. Zipper fly only, please!
And in case in makes a difference, I'm a male in my late 30s, living in NYC. Thank you so much for your help!
posted by Conrad Cornelius o'Donald o'Dell to Clothing, Beauty, & Fashion (7 answers total) 2 users marked this as a favorite
Should I be wearing belts with these pants?

If you're going to tuck your shirt in, then absolutely yes you must wear a belt. If you're not going to tuck your shirt in, I would still say yes. Belt should match your shoes... are you planning to wear the shoes pictured with these pants? I would only wear those with jeans.

I wouldn't wear Shirt 4 with Pants 6 and I wouldn't wear Shirt 4 alone with black pants or you'll look like a waiter. Shirt 4 should go with navy or gray pants. Most of the rest goes together as far as I'm concerned, except I wouldn't wear all black or all navy.

Frame of reference: I'm female, late 30s, was married to a guy whose wardrobe looked almost exactly like this (except for the shoes).
posted by desjardins at 9:41 AM on September 15, 2014

1. Pretty much any color socks except white.

2. Re shoes and really everything matching in general -- there's an odd divide here between casual and what to me looks like business formal. Like you have a bunch of dress shirts that look like they'd be worn with suits, and also some dress pants, and a casual leather jacket, casual chinos, casual sweaters, and sneakers. So in terms of shoes, dress shoes to go with all the dress pants and dress shirts. The sneakers will be fine with the chinos and sweaters. In terms of matching stuff overall, I think you could wear any of the light colored dress shirts with any of the dress pants. The black, grey, and deeper blue dress shirts I would return since they only match the chinos, which are too casual to wear together.

3. Yes, unless you plan to wear your shirts untucked.
posted by Sara C. at 9:48 AM on September 15, 2014

Wear cool socks. Those are cool shoes so wear cool socks. Here is a cool sock you can wear with those shoes. Here is another.

For jeans, just go with Levi's. They're a classic, available in a host of different cuts to fit whatever sort of ass situation you have going on, and aren't going to have any sort of silly trendy flair to them.
posted by phunniemee at 10:00 AM on September 15, 2014

That is a set of extremely basic clothes, that virtually all go together. Just don't wear all black, and don't wear black and navy together (because that tends to look like an accident and you meant to wear all black or all navy). Contrast between tops and bottoms is good. Agree on yes to belts.

And I also agree with Sara C, depending a bit on what industry you're working in. Be careful with dark tops & dark bottoms together, and if you want to supplement your wardrobe go somewhere where you can get some nice patterned shirts.
posted by brainmouse at 10:22 AM on September 15, 2014

I agree about not wearing a white shirt with black pants because it does make you look like wait staff. Otherwise, they all go together and I think navy and black are fine, too. If men's pants have belt loops, wear a belt.

I think you should start wearing interesting socks, but I think it'll take you some time to get used to that. Start with polka dots, stripes, small patterns in muted colors, and get bolder as you get used to it. I wouldn't wear blue socks with brown pants and vice versa, but socks that are not too far off the dark-/light-ness of the pants are fine. As you get used to what colors you like together, the socks can be quite an interesting addition.
posted by theora55 at 10:57 AM on September 15, 2014

These are all pretty neutral and you should be safe with most combinations. My husband basically goes through a sweater + shirt + trousers combo every winter. He has gotten more experimental lately with patterned shirts and different kinds of collars for sweaters.

My tips:
- Top lighter than the bottom but avoid too much of a contrast like white+black
- Your black sweater will go with all of your shirts (except black) and all your trousers (except black) so go mix/match crazy with that one.
- The red sweater I'd pair with 4 (white) or 10 (beige). 6 (pink) if you think you can pull it off (I think you could as long as you are not a redhead?). I think you're good to go with any of your pants depending on the formality of the situation. Depending on the occasion, your style, and the length of your shirt you may possibly be able to get away with it untucked with pants 2, 3 and 6.
- Always wear a belt. To be safe: 1 shiny black, 1 matte black, 1 matt brown, all leather. Match with your shoes.
- Love the shoes. I think you can wear them with pants 2 and 3, matte black leather belt.
posted by like_neon at 11:52 AM on September 15, 2014

Response by poster: Thanks, everyone. I am pretty young-looking for my age (sometimes described as having "boyish" looks). I also work from home alone, so these are not intended to be work clothes.
posted by Conrad Cornelius o'Donald o'Dell at 4:20 PM on September 15, 2014

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