Ask the Edit: A Men’s Fashion Question

Jan 5, 2018

Hi Belle,

Can you help me with men’s fashion? My boyfriend is 6’6″ and hates shopping, so he would just buy whatever fit that was on sale, so his wardrobe definitely needs an upgrade. Since I love shopping and will do it for him, he’s not opposed to upping his style game…I’m just not entirely sure where to start. I can look at a man’s outfit and know if it’s stylish, but buying actual pieces is harder. And I wouldn’t really know what basics belong in a man’s wardrobe these days. Do you have any tips or resources you can share?

– Anna 

I don’t, but I’m sure Kyle does.  So let me tag him into the game.

The guiding principal with men’s fashion is fit.  Let me say that again, the guiding principal of men’s fashion is FIT! (But we’ll get back to that.)

The range of available style options is much more limited than women’s fashion. There are no dresses, few accessories, and if he wears leather pants…well, we have much bigger issues to cover. The simplicity of men’s fashion is great and difficult at the same time. Most of your clothes will work in conjunction with one another, but you’re occasionally going to wind up looking like you and a coworker planned outfits. #twinsies

Back to your boyfriend, for someone 6’6” and a medium build… the rack doesn’t exist, it’s “not a thing” as the kids say.  Which leads us back to fit…

Shirts. You need to measure your boyfriend (his sleeve, neck, and chest) and buy shirts that are cut to fit. An ill-fitting shirt (too big, sleeves too short, buttons pulling) wrecks the rest of the outfit. Shirts are your foundation, spend accordingly.  You should be spending minimum $60+ per shirt. Look for thicker material; thin material wrinkles and requires an iron or steam almost no-matter what.

Start at Nordstrom Rack; they have shirts sold by neck size, sleeve length, in all price ranges, and colors/patterns. Start with blues, purples, and whites. In both patterns and solid colors. These colors work with both brown and black foundations (shoes and belts) allowing for the most overlap.

Shirt Suggestions: Hugo Boss Plaid Shirt ($59) // BR Gingham Camden Shirt ($79, also in tall) // Club Monaco Cluster Dot Shirt ($79)

Pants. Again, fit. This isn’t a “what is your waist size” and done. You need an inseam measurement and more than likely you’re going to be getting them tailored. (With Nordstrom’s, or Rack, basic alterations are free).

Even more important than shirts, spending a little more on pants is critical. Once guys find a pair of pants they like, they keep them around. You don’t want them to wear out quickly and him to keep wearing them long after they’ve expired.  Then, you’re dating faded pants guy.

Dark Jeans are quickly becoming the standard. If you read my holiday guide, AG’s are my current favorite brand.  I was a 7’s guy way back; they make a good jean, too.

Look for jeans with as little spandex in them as possible. The more cotton, the longer they last and hold their shape.

Full disclosure, I’m not a fan of khakis for any reason. While I understand they serve a purpose, I feel like there are better options. Grey, blue, purple, red, or dark brown jeans and trousers.  Color is your friend.

Pant Suggestions: Lacoste Slim Fit Corduroy ($125) // Bonobos Slim Wash Chinos ($98) // AG Slim Straight Jeans ($178)

Shoes. I would be happy to write a whole post on just shoes, but I will keep this short(ish). You need six pair of staple footwear. A simple dark brown dress, a patterned light brown dress, a brown boot, a dress sneaker, a simple black dress shoe, and a trendy black dress shoe.  (Don’t listen to him, I would be grateful if all he had were six pairs of shoes.  Also, you can probably get by with three to start.)

Men’s shoes are unlike women’s shoes; there is no such thing as a good looking pair of cheap men’s shoes. Good shoes are going to be expensive. The good news, styles don’t change much and shoes last forever if they’re cared for. Between polish and resoling, a good men’s shoe can last for years.

To Boot NY and Taft are both great brands.  I’ve walked a mile in each, so I can personally recommend all of them for quality and comfort.  Lastly, as an aside, if your boyfriend has square-toed dress shoes that are any wider than your knuckle throw them away.  So dated.

Shoe Suggestions: Taft Jack Boots ($250) // Cole Haan Williams Wingtip ($120) // To Boot NY Oxfords ($160)

Jackets. As a guy, sport coats are your best friend. They take an average outfit to dinner party ready. Blue of all shades and pattern, colors for summer, black for nights out, Herringbone for a rare fall occasion.  Buy a jacket or two, wear them, maybe (if you’re brave), add a pocket square.  (Get ready to be folding pocket squares and commenting on the folds of pocket squares, ladies.)

Jacket Suggestions: Brooks Brothers Regent Fit Camel Coat ($280) // Slim Navy Blazer ($248) // Boss Teal Mini-Dot Sport Coat ($245)

Sweaters. Again, sweaters could be a whole post. Keep to simple sweaters, no patterns when you’re starting out.  Choose thin-to-medium materials (cashmere, if you want to splurge); heavier sweaters just add bulk.  Also, avoid sweaters that are too short, unless you want your boyfriend to look like a cartoon character.

Sweater Suggestions: Ted Baker Quarter Zip ($114) // J.Crew Melange Sweater ($75) // Todd & Duncan Cashmere Crew ($198)

{image found here; this post contains affiliate links}



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  1. Rebecca says:

    Anna could also consult He has some great resources for tall (and average-build!) guys.

  2. Madeline says:

    Great post! I would add investing in some great undershirts that fit well and have nice lay-flat collars. I can’t tell you how many times I’ve seen a guy with a nice sweater or half-zip with a gross, rumpled collar of a free t-shirt peeking out, ruining his look. Or NO undershirt at all, which can be very off-putting, especially if you have chest hairs that are out of control. *gag*

  3. Monica says:

    Fold your own pocket square, Kyle.

    • Melissa says:

      Bahhhhh … I had the exact same thought!

    • Margaret says:

      I disagree – I love doing little things like this for my guy. Teamwork makes the dream work.

    • Kyle says:

      There was some editorializing once this post was handed over for publishing! I always fold my own…

    • Belle says:

      I fold them rarely, comment on the folds daily. It can be funny, other times, it’s like, honey, no one cares.

      • anna says:

        Haha, I think it reads like ladies should be prepared to fold the squares as if it’s our duty, but I totally get what you mean. My bf is super fiddly with pocket squares and constantly second guesses himself, so he asks me to help. I think it’s kind of cute, since they have so few accessories to fuss over.

  4. alison says:

    I love this post, thank you! My tangential question would be this: what’s the best way to go about helping a guy clean out his closet to make room for these more stylish options? My husband’s side of the closet could use a serious paring down but I’m not sure where to start.

    • Amber says:

      Maybe I am pushy, but I just tell my husband we are going to clean out the closet. Then I go through each item with him, pointing out things that look worn out or that he hasn’t worn in a while (say 6 months). If there’s a question about whether something still fits I make him try it on. If it doesn’t fit it gets donated. I used to try just suggesting that he do it on his own but after 10 years I realized that wasn’t going to happen.

  5. Alice says:

    I have a brother that is 6’5″ – find the retailers with tall sizes for casual shirts, including tees. Important whether tucking in or not. I’m tall myself and hate feeling like I’m constantly tugging things down. Jcrew and Land’s End are usually where bro’s Christmas presents come from, but those stores also fit his style – ymmv.

  6. Jen says:

    My fiance is a taller/bigger guy as well. He has about 20 button down shirts from Brooks Brothers and when I saw how much they cost I was shocked. However, the quality is AMAZING. He has had some for 15+ years and they look just as good as his newer ones. No ironing needed and he even puts them in the dryer. Plus, a nice button down has so many uses. Wish I could find pieces that were as good of a value!

    • J says:

      +1 brooks brothers non-iron shirts. they make them for both men & women. yes, very pricey but when you calculate the cost per wear, totally worth the investment. they really do come right out of the dryer looking like they were pressed! (even the cuffs and collar)

  7. anne says:

    Mom of several very tall boys here — at 6’6″ don’t expect to easily buy off the rack, especially if your guy is on the skinnier side. For my 6’8″ son-in-law we’ve had pretty good luck with Indochino for relatively affordable chinos, dress shirts and suits. We’ve never really found jeans that work. Lands End has decent tall sweaters for guys; Banana Republic sometimes does, although they still seem fairly short. For my 6’4″, 145lb son, we’ve found that Uniqlo carries pants in narrow waist sizes in a 34″ inseam. They also tend to be skinnier in the leg, which works better for him. If anyone has any other sources, I’d love to know about them.

    • Kerry says:

      I would also add Zara and Ted Baker to this list. Ted Baker is the only brand that fits my tall/slim husband off the rack. The price point it high, but its probably worth it considering he has to get everything else tailored. Nordstrom usually has a great selection!

    • anna says:

      Try a 6’4″ former football player with thighs like tree trunks. Either nothing fits or it looks like it’s meant for someone obese who wants to hide in a sack.

  8. Libbie says:

    Two questions: (1) Do you have any recommendations for extremely wide men’s shoes? My fiancé needs at least 4E and I haven’t found any reasonable looking dress shoes anywhere! (2) Where can I find him some tall AND slim clothing? Most tall stuff is far too bulky. Is tailoring his only option?

    Thanks so much!

    • Belle says:

      There’s a shirt brand called Hugh & Crye which might be worth a look. Their shirts are sized differently to accommodate slim and wide.

  9. Elle says:

    *guiding principle

  10. Monica T says:

    I’ve been dressing my husband for a while now, if it was up to him he’d be wearing too big….everything…but mostly too big relaxed fit cargo Dickies! Some men are all about comfort, but there comes a point, or an age, where you have to up your game. Kyle is right that FIT is what matters most, and quality is a very close second. Figure out your guys body type and then read some Esquire articles about suits and styles that flatter that shape, it really helps when you’re shopping!

  11. J says:

    Love everything about this post. Thanks to both of you!

    • Allison says:

      Yes yes yes! Thank you both. My husband is a t shirt and jeans guys, which I love, but as we get older and his career progresses he can’t get by looking like a schlubby intern. And even though I think I have a pretty solid hold on women’s fashion, I had no idea when it comes to men. When I try and search men’s fashion blogs to try and understand the “rules”, they are always waaay to fashionable. He would never consider even cuffing a jean or touching a scarf. I really appreciate that this is more realistic, classic without being Dad. Kinda like Abra’s suggestions, classic but still fashionable. 🙂

  12. A.J. says:

    can you elaborate on “dress sneaker”? because I think my husband could use such a thing but I can’t envision exactly what it’d look like.

  13. TheLOOP says:

    For the first 10 years of my marriage I lamented my husband’s sloppy dress sense and his belief that the only colors that exist are ones that start with B – black, brown, beige and blue. Then in the last 6 months, he went through a career transformation and started dressing really smartly and dare I say, a bit preppy – tailored suits, nice quality sweaters, shoes that aren’t split at the seams, dressy coats etc. While I LOVE how he looks, I did not bargain for the need for feedback on whether the pleat is perfect, whether the shoes go with the belt and yes, whether the pocket square is folded just so. Like Belle says, honey, no one cares.

  14. Sharon says:

    Despite being a single lady, I adore this post and everything about it, including Abra’s shoe comments. How many pairs do you really have, Kyle?

  15. Love this post! My husband isn’t tall, but he does need a bit of encouragement to break out of his t-shirt and hoodie tech man uniform. He has good trousers and denim, and wears decent Clarks oxfords everyday, but finding an alternative to the hoodie is a struggle. One of his holiday gifts this year was a cotton-cashmere sweater from Nordstrom – still soft and warm, but just a little nicer.
    He loves Indochino for (rarely used) suits, blazers, and button-ups. You can get really good deals on their made-to-measure shirts especially.

  16. Claire says:

    My husband orders a ton of his dress clothes online.. Paul Frederick is a great place for shirts (if you ignore the dad-style of the website you can find literally every size, color and fit option) and suits, vest, sport coats can all be gotten made to measure from Indochino.

  17. Beth says:

    My husband loves MTailor. They make custom shirts, jeans, and suits that are priced about the same as Nordstrom or J. Crew. You get measured using your phones camera, clothes are delivered in two weeks, and you get free remakes or returns.

  18. Anna says:

    Thanks Belle, Kyle, and everyone for all the tips in the comments too!

  19. Martha says:

    Thanks, this is helpful. My fiance wears some form of a polo shirt and khakis EVERY day to work. I finally convinced him to at least get some in other colors than red and to buy a sport coat and have his dress pants tailored for when he needs to do presentations and attend formal events. He’s hard to shop for because he’s 4.5 feet tall and wears a men’s 3 shoe or a kid’s six.

  20. Colleen says:

    My husband is 6’5″ and most stores do not have clothes that fit him well – including Nordstrom and Nordstrom Rack, J. Crew, Banana Republic. Many of the brands you mention can be on the expensive side and have very slim fit clothing which doesn’t work well for athletic builds.

    The only exceptions where we’ve had luck is with dress shirts at Nordstrom and the occasional suit at Nordstrom Rack.

    For inexpensive casual t-shirts and button-ups, I recommend the big and tall section at Kohl’s.

    For casual activewear – tshirts, shorts – try Columbia’s tall sizes online. Kohl’s also carries big and tall Nike sizes.

    For khakis, jackets etc. try Land’s End and L.L. Bean tall sizes. We also love Eddie Bauer tall sizes for shorts that are long enough for taller guys.

    For denim, I highly recommend Lucky Brand Jeans. They can be pricey, but we’re fortunate to have a Lucky outlet store near us and often have good luck finding them on the racks at Steinmart too,

    In terms of suits, aside from a lucky trip to Nordstrom Rack, if we’re shopping for a specific type of suit we have to head to a department store like Dillard’s or Macy’s, or Men’s Wearhouse when they have good sales to have something custom-tailored to fit.

    Good luck!

    • anna says:

      Great suggestions. There seem to be a lot of options for tall and “big” and increasingly more for tall and slim, but not a whole lot for tall and athletic builds.

  21. Lynn says:

    Duluth Trading Company is the only place where I can get clothing that both fits my 6’6 husband and lasts. The quality is great and they have everything from casual wear to more office-appropriate styles.

  22. Jennifer says:

    Great post and loved reading the comments. Another thought may be investing in an image or wardrobe consultant. Yes, these exist for men and perform the same functions as an image/wardrobe consultant for women. While the service is not free, they can save both you and your SO a significant amount of time (and eventually $$) by taking a full set of measurements, directing your guy toward online and B&M stores that carry clothing in their fit range and style preference, and providing guidance on fit, fabric, classic styles, and pulling everyday and special occasion outfits together. Men don’t always ask for directions, but they are pretty good at following them ????. It can also be informative for many of the female commenters who want to help but don’t know where to start. For some couples where the guy has priorities other than fashion, bringing in a third party can also take out the dynamic of a perceived nagging girlfriend or wife. The final alternative may be the two of you watching Ryan Gosling work his magic on Steve Carell in “Crazy Stupid Love” which comes with the benefit of Ryan Gosling’s abs ????

  23. Tammy says:

    My husband is also 6’6″ and has a slimmer profile so its always a struggle to buy him anything. Here are his favorite brands:
    – Suit Supply (for collared shirts)
    – Banana Republic (for chinos and khakis)
    – Ted Baker (for blazers, sweaters and collared shirts)
    – Barbour (classic jackets that are pricey but will last forever)
    – LL Bean (for winter wear options)
    – Pladra (unique plaid shirts with cool animal patterns at the cuff and collar)
    – Abercrombie (for jeans – as a 30 something this makes me cringe but whatever fits!)
    – Wolverine (1,000 mile boot – he’s kept them in his closet for the last 7 years and they go with every casual outfit you can imagine)

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