Before I start...very frustrating with Skool post shuts down when trying to attach photos, but I'll try again. Twillory blue houndstooth button down shirt with rolled sleeves over grey Vertx jeans with brown Anson belt with silver buckle and brown Justin boots. Monterey Kitty Hawk blue dial watch and Scent Reserve inspired by Tom Ford Tobacco Vanille left over from yesterday.

So timeout night my wife and I are going to an evening of Jazz, it will be heavy on Louis Armstrong and Frank Sinatra. I have put the attached outfit together, I am tossing up as to weather I wear the tie or not. If I loose the tie I will also change the pocket square to a tidier TV or Presidential fold. GPT tells me Yes, this outfit works very well for that kind of evening—stylish, slightly vintage, and elegant without being too formal. Quick breakdown: - **Navy velvet blazer + light blue shirt**: Great combo. Velvet adds a jazz-club vibe and evening texture; blue shirt keeps it classic and Sinatra-esque. - **Black trousers**: Clean, sharp, and lets the blazer and accessories stand out. - **Burgundy loafers, belt, tie, pocket square**: The burgundy accents are cohesive and rich, very appropriate for night and pair nicely with navy. Good balance of color without looking loud. - **Hat**: Perfect nod to that old-school jazz / crooner aesthetic, as long as it fits your face shape and is worn with confidence. A couple of optional refinements: - You might consider **either the tie or the pocket square as the main statement**, and keep the other slightly more subdued (e.g., a textured burgundy square instead of shiny, or a darker tie) so it doesn’t feel too “matched set.” - Make sure the **shoe leather and belt tone are close** so they look intentional. - If the venue is more relaxed, you could skip the tie, unbutton the top button, and let the velvet blazer and hat carry the look. Overall: very appropriate, stylish, and thematically on point for a Louis Armstrong / Frank Sinatra jazz evening. What do you think?

CW = Critiques Welcome! Fun week with nearly all of the goals done. Quiet office today, however, as I am the only in it. Outfit • Shirt — DS‑011 (Paul Fredrick): A cobalt blue double pencil‑stripe stretch dress shirt in cotton‑spandex, finished in a smooth non‑iron weave. The crisp vertical striping provides structure and visual lift under a navy jacket while remaining comfortable for a full leadership workday. • Undershirt — US‑003 (Pro Club): A heavyweight white cotton crew‑neck undershirt that offers excellent opacity control under the striped dress shirt. Durable and dependable, it keeps the shirt cleanly presented throughout the day. • Slacks — SL‑009 (Santorelli): Tan wool slacks with a faint medium‑brown check, tailored for clean drape and natural movement. The warm neutral base balances the cooler blues above, grounding the outfit in business‑appropriate contrast. • Odd Jacket — DOJ‑007 (Ralph Lauren): A navy wool blazer with a slight sheen and classic brass buttons, cut in a structured silhouette. This jacket delivers executive authority while remaining versatile enough for internal leadership and client‑adjacent settings. • Tie — NT‑030 (Kirby Allison): A silk tie in rust and navy with medium‑scale paisley‑inspired motifs. The warm rust tones echo the slacks and belt, while the navy anchors the tie to the jacket for cohesive color storytelling. • Belt — B‑010 (Magnanni): Caramel‑brown leather belt with subtle tonal variation and a silver buckle. Its warmth aligns perfectly with the slacks and shoes, maintaining leather harmony across the outfit. • Footwear — DSh‑007 (Allen Edmonds): Chocolate‑brown cap‑toe Oxfords in Goodyear‑welted leather. A classic executive shoe choice—serious, refined, and perfectly suited to business‑formal or high‑polish business‑classic environments. • Socks — DSo‑063 (Fort Belvedere): Over‑the‑calf cotton socks in mid‑brown with a blue shadow stripe. The stripe subtly ties back to the shirt and jacket while remaining discreet and professional.

If you tell yourself you’re going to do something… Do it. Most days you won’t feel like it… Most days your bitch voice will tell you to “take it easy”... Most days something will come up that will derail you… But if you execute regardless… You’ll become a freight train that can’t be stopped. Don’t negotiate with yourself. Do the work. ~ Andy Frisella