How to Style Denim in Your 20s 30s & 40s w/ 40overfashion

How to Style Denim in Your 20s 30s & 40s w/ 40overfashion

Today we have our good friend John Galfano (@40overfashion) in the studio! We put together three different looks for you to gain inspiration to step outside your comfort zone and style denim at any age!

Check out John’s Channels:





Our Favorite Videos:

The Best Boots Under $250 –
How to Style Chelsea Boots –
Suit Supply or Indochino Suits? Who Makes the Better Suit? –
Double Breasted VS Single Breasted Suits –
The 5 Best Jackets for Spring –
10 Casual Shirts PERFECT for Spring and Summer –
How A Properly Fitted Suit Should Fit –
6 Ways to Wear White Sneakers –
5 Reasons To Dress Like You Give A Sh*t –

How to Grow Your Beard and Keep it Looking Fresh –
How I Get My Hair Cut || How to Ask For a Haircut –
5 Huge Haircut Mistakes –

How To Cook The PERFECT Steak in 2 Minutes! –
Gent’s Lounge Cookbook: Bacon Frittata –
Gent’s Lounge Cookbook: My Favorite Breakfast –
Gent’s Lounge Cookbook: Avocado Toast –

5 Cocktail Terms Every Gent Should Know –
Whisky 101: How to Taste Whisky –
10 CHEAP Whiskeys You Should Buy TODAY –

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Follow Blake on Instagram –

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#gentslounge #menswear #likeagentleman #40overfashion


  1. Wilson Negrini on March 17, 2022 at 5:17 pm

    same haircut for the 3? Lack of style or personality?

  2. DEAR MR MAC on March 17, 2022 at 5:20 pm

    Blake all the way

  3. mookeychase0907 on March 17, 2022 at 5:20 pm

    I like em all prob wouldn’t rock the T wit George’s fit but Im lookin at who’s haircut is the slickest…

  4. Donald Bingwa Armando on March 17, 2022 at 5:21 pm

    Blake for the Win. I am in my late 30s

  5. BoBo Innovation (Recoil-Savvy Nersofter) on March 17, 2022 at 5:22 pm

    Why everybody in the film kept rubbing their hands?

  6. Rick Terscale on March 17, 2022 at 5:22 pm

    With "Classic" tailoring, the fashion styling works across all ages. If you have the body, the form, the look, then it shouldn’t matter too much what your age is.
    When it comes to distressed, vintage, ripped jeans styles … these are better suited to younger generations.
    But older guys need to be careful not to dress in a way that actually makes them look older than they are. John’s cardigan and shirt make him look older than he is.
    Also take care with color! Color is so important. That light/cool blue shirt with silver hair and pale complexion doesn’t work. A white shirt would have provided better contrast with the rest of the outfit. Or even a shirt that had similar/close coloring to the shoes would have been magic!! A warmer colored shirt would have set off the darker, warmer look perfectly.

  7. Rene Vacio on March 17, 2022 at 5:24 pm

    Great video. I like the look and I’m just know trying on jackets and currently only own boots, like Thursday, Taft, and Siminon Becket. And I was looking for looks on the web with that combo and there isnt alot so I was wondering if yall could do a video like that? Like what you guys do.

  8. James Garvey on March 17, 2022 at 5:24 pm

    What brand is that knitted blazer??

  9. FloridaGary E on March 17, 2022 at 5:26 pm

    John’s look is more polished. Nicely done.

  10. Sonny on March 17, 2022 at 5:28 pm

    Great Video. Thank you for posting.

  11. Dylan Lundgren on March 17, 2022 at 5:31 pm

    Where are Blake’s jeans from?! Love that wash.

  12. Luis Quintas on March 17, 2022 at 5:34 pm

    Pongan, subtitulos en español gracias.

  13. rdefabri on March 17, 2022 at 5:34 pm

    In my 50’s, so @40overfashion has it right for me. I sometimes wear loafers / no socks, and lighter wash, but primarily dark wash with boots or brogues.

  14. Narciso Veloz on March 17, 2022 at 5:36 pm

    Tell people not to be obese and after that they can wear anything and then they would look fine even if they wear clothes from the goodwill store.

  15. Q-Storm76 on March 17, 2022 at 5:38 pm

    I’m in my early 40s, but strangers always mistaken me for a 20 something guy so I can go either way 😊 with footwear and apparel

  16. Truth Hurts on March 17, 2022 at 5:38 pm

    Where can we get this denims?

  17. Juan Carlos Jimenez on March 17, 2022 at 5:38 pm

    I’m in my 40 s but love Blake’s outfit : such very versatile.

  18. travis mayhew on March 17, 2022 at 5:40 pm

    I like George’s look for the clubs

  19. Fall Front 21 on March 17, 2022 at 5:41 pm

    In my fitties—who gives a fuc#

  20. ponypower8 on March 17, 2022 at 5:43 pm

    All 3 styles look great. John’s getup is age and size appropriate for me. I even think it’s also appropriate even for young professionals. I’ve always been a fan of smart casual, kinda Ivy League vibe or Ralph Lauren style, so I think John’s getup looked awesome.

  21. Jim Klemens on March 17, 2022 at 5:44 pm

    Why didn’t anyone roll their pants up?

  22. Andy on March 17, 2022 at 5:44 pm

    The younger look would look fine on any age if the jeans weren’t all ripped and distressed.

  23. SoulDilah on March 17, 2022 at 5:51 pm

    Good video!!

  24. Tommy Gamba on March 17, 2022 at 5:53 pm

    Those shoes just don’t go with the shirt shoes are too light too nice for the shirt in the pants. It’s a bad pairing for the 20s age. Because it’s bad style for any age

  25. Bright Hosea on March 17, 2022 at 5:53 pm

    Thanks guys for throwing a light on this subject matter because am 44yrs old and I sometimes feel uncomfortable wearing denim jeans with Chelsea boots because I always thought am too old for such dressing.

  26. Michael Brown on March 17, 2022 at 5:54 pm

    What color belt did George wear?

  27. Roco 61 on March 17, 2022 at 5:54 pm

    I don’t agree about not wearing certain denims because of your age. I feel like if you put it together right and you feel good in it , rock it!

  28. Donna Arnold on March 17, 2022 at 5:55 pm

    John what brand and style are your jeans please?! Love your look!!

  29. Squadra916 on March 17, 2022 at 5:55 pm

    Great video and advices. I’m 35 but look wery young. Half of my jeans are dark denim(for more dressy look) a second half more like blue or dark blue jeans for more casual outfits(hoodie, tshirt). Very lightwash only for summer vey casual occasions. I need try dark grey jeans i think its the proper choice for olders with jeans colours

  30. Omar Salih on March 17, 2022 at 5:56 pm

    I don’t think Jon’s cardigan color fit the outfit the best. Just my opinion. I would go with black denim with that charcoal gray cardigan, love it btw.

  31. Kenny Gibson on March 17, 2022 at 5:56 pm

    Follow John s page so 40 over four me lol play on words.

  32. Jim King on March 17, 2022 at 5:56 pm

    There’s nothing wrong with light blue denim for any age, especially in the summer. Just stay away from raggedly holes in the knees or fake ageing. That looks stupid, for anyone, at any age.

  33. Raj Krish on March 17, 2022 at 5:57 pm

    Awesome… 2 of my fav style youtube icons. 👌

  34. winwinwin282828 on March 17, 2022 at 5:57 pm

    2, 3 1 for me , nearing 50.

  35. Rolando Vera on March 17, 2022 at 5:57 pm

    Guuuaaauu…so nice,so cool thanks a lot.

  36. Tim Mac on March 17, 2022 at 5:59 pm

    What if you’re a creative type, all these styles look like they’re for accountants or for people who work in a government office

  37. Edward Witherspoon on March 17, 2022 at 6:03 pm

    I feel with my age now I have to go with John. But George and Blake are my Guy’s. Keep up the good videos.

  38. Richard Long on March 17, 2022 at 6:04 pm

    John I like the sweater/jacket you wore in the video–kind of dressy, kind of casual. Blake, please drop the "I feel …" reference when you are relating a belief or opinion. Feelings are happy, sad, mad, glad, not your thoughts about clothing choices. Overall, helpful collaboration when it comes to figuring out this age and style/fashion issue.

  39. Shogo bXpG7!5 on March 17, 2022 at 6:05 pm

    they look like Italian mobsters 😭😂❤️

  40. P C on March 17, 2022 at 6:06 pm

    its perfectly normal and cool to wear skinny or slim lighter jeans with maybe some kneeholes when your 40 plus , it really doesn’t mather how old you are.
    No one ever should say what you have to wear for your age

  41. Rook on March 17, 2022 at 6:06 pm

    Do you mind listing the brands of jeans you’re wearing please? Thanks!

  42. Chris Hanlon on March 17, 2022 at 6:08 pm

    Can you list the link to the clothes, watches, and belts in this video (or share the brands/models)?

    I am particularly interested in finding the brand of the knit cardigan blazer.

  43. Maria Lopez on March 17, 2022 at 6:08 pm


  44. eshtylla on March 17, 2022 at 6:11 pm

    None of them looked good nor right. Useless content

  45. New Nobles & Co. on March 17, 2022 at 6:14 pm

    Blake killed it!!!

  46. Maple Hedgehog on March 17, 2022 at 6:14 pm

    I just turned 40. I want to wear distressed denim…..especially since i’ve been a musician and up on stage with that Rockstar Look. I’m 6’4" too with a belly so, i’ve been told to try n wear light color pants to drape over my chicken legs and darker tops to mask the chub.

    But i have to admit, John looks the slickest. Dammit…..i don’t want to dress 40.

  47. Bright Hosea on March 17, 2022 at 6:14 pm

    Thanks guys for your help

  48. TRISMUSIK on March 17, 2022 at 6:15 pm

    Wear whatever you want guys. I wear all 3 looks shown in this video and I’m 37.

  49. KurJan&Urbano on March 17, 2022 at 6:16 pm

    None of you wear hats???
    Just not sure your style can be trusted…

  50. MICHAEL on March 17, 2022 at 6:16 pm

    Nice video Gents!! Each look is perfect for the age range that they represent…
    For Blake’s look…
    Some say don’t wear a pocket square if no tie is being worn b/c ties and pocket squares are indicative of a dressier look not for casual wear. Your thoughts…??